HALOGEN DERIVATIVES.pdf

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CONTENTS EXERCISE - I (A) EXERCISE I(B) EXERCISE - II EXRECISE - III EXRECISE - IV(A) EXERCISE IV(B) ANSWER KEY EXERCISE–I (A) (Choose the correct option. Only one is correct) Q.1 Which one is liquid at room temperature: (A) CH3Cl (B) C2H5Cl (C) CH3Br (D) C2H5Br Q.2 The correct order of melting and boiling points of the primary (1°), secondary (2°) and tertiary (3°) alkyl halides is: (A) P > S > T (B) T > S > P (C) S > T > P (D) T > P > S Q.3 Pick up the correct statement about alkyl halides: (A) They show H-bonding (B) They are soluble in water (C) They are soluble in organic solvent (D) They do not contain any polar bond Q.4 What would be the product when neopentyl chloride reacts with sodium ethoxide: (A) 2-Methyl-2-butanol (B) Neo pentyl alcohol (C) Both 1st & 2nd (D) 2-Methyl-2-butene Q.5 Reduction of alkyl halide by LiAlH4 is the type of reaction: (A) Nueleophilic substitution reaction (B) Electrophilic substitution reaction (C) ElectrophilicAddition reaction (D) None of these Q.6 2-methyl butanoic acid is formed by the reaction CHCl3, NaOH and (A) Propene (B) Ethene (C) 1-Butene (D) 2-Butene Q.7 CCl4 + KOH (excess)  end product of the reaction is: (A) K2CO3 (B) CO2 (C) C (OH)4 (D) HCOOK Q.8 The yield of alkyl bromide obtained as a result of heating the dry silver salt of carboxyic acid with bromine if CCl4 is: (A) 1° > 3° > 2° bromides (B) 1° > 2° > 3° bromides (C) 3° > 2° > 1° bromides (D) 3° > 1° > 2° bromides Q.9 Which of the following statements is invalid: (A) The more stable the carbocation the faster it is formed (B) Propyl cation changes to more stable isopropyl carbocation by 1,2 shift of a hydrogen (C) Isopropyl chloride reacts with sodium ethoxide to form 1-ethoxypropane (D) Propyl halides reacts with sodium ethoxide to form 1-ethoxypropane Q.10 Nitrochloroform is prepared by the action of chloroform and: (A) Hot aqueous solution of KNO3 (B) Hot aqueous solution of NaNO2 (C) Hot concentrated nitric acid (D) Hot dilute HCl + aq. NaNO2 solution Q.11 Which of the following compounds is most rapidly hydrolysed by SN1 mechanism. (A) C6H5Cl (B) Cl–CH2–CH = CH2 (C) (C6H5)3CCl (D) C6H5CH2Cl O || Q.12 CH3MgBr + CH2  CH  C  H OH | (A) CH2  CH  C  H | CH3  H2O product (major), product is (B) CH2  CH  CH  CH3 | OH (C) CH3–CH2–CH2–CHO (D) None is correct Q.13 Which is incorrect about Hunsdicker reaction? (A) Only Cl2 can give alkyl halide (B) I2 will give ester when treated with RCOOAg (C) The reaction proceeds through free radical (D) F2 cannot give alkyl halide Q.14 Major product for the reaction Br2  is: hv (A) (B) (C) (D) Q.15   II B   I A Steps I and II are (A) both SN1 (B) both SN2 (C) ISN1, II SN2 (D) I SN2, II SN1 Q.16 What are A& B in the following reaction? Mg /THF A (i) CH3CHO  B (ii) aq.NH4Cl (A) & (B) & (C) & (D) None of these Q.17 Ester A (C4H8O2) + CH3MgBr   C4H10O (2 p

CONTENTS
EXERCISE - I (A)
EXERCISE I(B)
EXERCISE - II
EXRECISE - III
EXRECISE - IV(A)
EXERCISE IV(B)
ANSWER KEY
ORGANIC CHEMISTRY
HALOGEN DERIVATIVES
EXERCISE–I (A)
(Choose the correct option. Only one is correct)
Q.1 Whichone is liquid at roomtemperature:
(A) CH3Cl (B) C2H5Cl (C) CH3Br (D) C2H5Br
Q.2 The correct orderofmelting and boilingpoints ofthe primary(1°), secondary(2°) andtertiary(3°) alkyl
halides is:
(A) P > S > T (B) T > S > P (C) S > T > P (D) T > P > S
Q.3 Pick upthe correct statement about alkylhalides:
(A) Theyshow H-bonding (B) Theyare soluble in water
(C) Theyaresoluble inorganic solvent (D) Theydo not contain anypolar bond
Q.4 What wouldbe the product whenneopentylchloride reacts withsodiumethoxide:
(A) 2-Methyl-2-butanol (B) Neo pentylalcohol
(C) Both 1st & 2nd (D) 2-Methyl-2-butene
Q.5 Reduction ofalkylhalide byLiAlH4 is the type ofreaction:
(A)Nueleophilicsubstitutionreaction (B) Electrophilicsubstitutionreaction
(C) ElectrophilicAdditionreaction (D) None ofthese
Q.6 2-methyl butanoic acid is formed bythe reaction CHCl3, NaOH and
(A) Propene (B) Ethene (C) 1-Butene (D) 2-Butene
Q.7 CCl4 + KOH (excess) end product ofthe reaction is:
(A) K2CO3 (B) CO2 (C) C (OH)4 (D) HCOOK
Q.8 The yield of alkyl bromide obtained as a result of heating the dry silver salt of carboxyic acid with
bromine ifCCl4 is:
(A) 1° > 3° > 2° bromides (B) 1° > 2° > 3° bromides
(C) 3° > 2° > 1° bromides (D) 3° > 1° > 2° bromides
Q.9 Whichofthefollowing statementsis invalid:
(A) The more stable the carbocation the faster it is formed
(B) Propylcationchanges to more stable isopropylcarbocation by1,2 shift ofa hydrogen
(C) Isopropylchloride reacts with sodiumethoxide to form1-ethoxypropane
(D) Propylhalidesreacts with sodiumethoxide to form1-ethoxypropane
Q.10 Nitrochloroformis prepared bythe actionofchloroformand:
(A) Hot aqueous solution ofKNO3 (B) Hot aqueoussolution ofNaNO2
(C) Hot concentrated nitric acid (D) Hot dilute HCl+ aq. NaNO2 solution
Q.11 Which ofthe following compounds is most rapidlyhydrolysed bySN1 mechanism.
(A) C6H5Cl (B) Cl–CH2–CH = CH2
(C) (C6H5)3CCl (D) C6H5CH2Cl
Q.12 CH3MgBr + H
C
CH
CH
|
|
O
2 

 
 

O
H2 product (major), product is
(A)
3
2
CH
|
H
C
CH
CH
|
OH


 (B)
OH
|
CH
CH
CH
CH 3
2 


(C) CH3–CH2–CH2–CHO (D) None is correct
Q.13 Whichis incorrect about Hunsdicker reaction?
(A) OnlyCl2 cangive alkylhalide
(B) I2 willgive ester when treated with RCOOAg
(C) The reactionproceeds throughfree radical
(D) F2 cannot give alkylhalide
Q.14 Major product for the reaction
hv
Br2


 is:
(A) (B)
(C) (D)
Q.15 II
OH

 


I
OH

 


B A
Steps I and II are
(A) both SN1 (B) both SN2 (C) ISN1, II SN2 (D) I SN2, II SN1
Q.16 What areA& B inthe following reaction?


 

THF
/
Mg
A
A
Cl
NH
.
aq
)
ii
(
CHO
CH
)
i
(
4
3



 
 B
(A) & (B) &
(C) & (D) None ofthese
Q.17 Ester A(C4H8O2) + CH3MgBr 
 


O
H3
C4H10O
(2 pair) (alcohol)
(B)
AlcoholB reacts fastest with Lucas reagent. HenceAand B are
(A) COH
)
CH
(
,
H
C
O
C
CH
|
|
O
3
3
5
2
3 

 (B) CHOH
)
CH
(
,
H
C
O
C
H
|
|
O
2
3
7
3



(C) CHOH
)
CH
(
,
H
C
O
C
CH
|
|
O
2
3
5
2
3 

 (D) COH
)
CH
(
,
H
C
O
C
H
|
|
O
3
3
7
3



Q.18 The hydrolysis ofalkylisocyanides (R–CH2–N
 C) gives
(A) RNHCOOH (B)
2
NH
|
COOH
CH
R 
 (C) RNH2 + HCOOH (D) RCH2NH2 + HCOOH
Q.19 What is product ofthe following reaction?
O
ET
Mg
2


 ?
(A) (B) (C) (D) None ofthese
Q.20 Following reactionis:

 


OH
(A) SE2 (B) SN1 (C) SN0 (D) SN2
Q.21 + OH–

 

2
SN A
A
Ais:
(A) (B)
(C) Both (D) None
Q.22 CHCl3 + OH–  HCOO–
Intermediates ofthis reaction are
(A) 

 3
CCl (B) 2
CCl

 (C) both (D) None
Q.23 Racemic mixtureis obtained due to halogenation of:
(A) n-pentane (B) Isopentane (C) neopentane (D) BothA& B
Q.24 For CH3Br + OH–  CH3OH + Br–
the rate ofreactionis givenbythe expression:
(A) rate = k [CH3Br] (B) rate = k[OH–]
(C) rate = k [CH3Br][OH–] (D) rate = k[CH3Br]°[OH–]°
Q.25 Whichwillgive white ppt. withAgNO3?
(A) (B) (C) (D) BothA& C
Q.26 The reaction ofSOCl2 onalkanols to formalkylchlorides gives good yields because
(A)Alkylchloridesare immscible with SOCl2
(B) The other products ofthe reaction are gaseous and escape out
(C)Alcoholand SOCl2 are soluble in water
(D) The reactiondoes not occurs via intermediate formation ofanalkylchloro sulphite
Q.27 True about alkylhalides is / are:
(A) Tertiaryalkylhalides undergo SN2substitutions
(B)Alkyliodides on exposure to sunlight graduallydarken
(C)Alkylchlorides do not give beilstein test
(D)Anucleophilicsubstitutionis most difficult inalkyliodides
Q.28 The product formed whenglycerolreacts with PCl5 is–
(A) 1,2,3–trichloropropane (B)Glycero monochlorohydrin
(C) Glycero dichlorohydrin (D)Allofthese
Q.29 On heating glycerolwith excess amount to HI, the product formed is–
(A)Allyliodide (B) Isopropyliodide (C) Propylene (D) 1,2,3–tri–iodopropane
Q.30 To prepare 3-ethyl-3-pentanolthe reagents needed are:
(A) CH3CH2MgBr +
O
|
|
CH
CH
C
CH 3
2
3 

(B) CH3MgBr +
O
|
|
CH
CH
C
CH
CH 3
2
2
3 

(C) CH3CH2MgBr +
O
|
|
CH
CH
C
CH
CH 3
2
2
3 


(D) CH3CH2CH2MgBr +
O
|
|
CH
CH
C
CH 3
2
3 

Q.31 Non-occurence ofthe following reaction
Br– + CH3OH  BrCH3 + OH–, is due to
(A)Attacking nucleophileis stronger one (B) Leaving group is a strong base
(C)Alcohols are not good substrate (D) Hydroxide ions are weak bases
Q.32 When ethylbromide is treated withmoistAg2O, mainproduct is:
(A)Ethylether (B)Ethanol (C) Ethoxyethane (D)Allofthe above
Q.33 When ethylbromide is treated withdryAg2O, mainproduct is:
(A)Ethylether (B)Ethanol (C) Ethoxyethane (D)Allofthe above
Q.34
OH
H
C
O
H
C
5
2
5
2


 


?Major product is:
(A) (B)
(C) (D)
Q.35 
 
 2
Br ?Product is:
(A) (B) (C) both(A) & (B) (D) noneofthese
Q.36
2
E
KOH
,
alcoholic




 
 A
A
(A) (B) (C) (D) None is correct
Q.37 To remove ‘phosgene’fromchloroform, _________ is added:
(A)Ethylamine (B)Ethylchloride (C) Ethylalcohol (D) Ethane
Q.38 Agemdichloride is formed inthe reactionexcept:
(A) CH3CHO and PCl5 (B) CH3COCH3 and PCl5
(C) CH2 = CH2 and Cl2 (D) CH2 = CHCl and HCl
Q.39
O
|
|
CH
C
CH 3
3


3
2
2
CO
Na
I

 
 (A) 


 

powder
Ag
(B)




 

Hg
SO
H 4
2 Product A, B & C are:
(A) Iodoform,Acetylene &Acetaldehyde (B) Tri. iodomethane, Ethyne &Acetone
(C) Iodoform, Ethene&Ethylene glycol (D) Ethene, iodoform&Ethylhydrogensulphate
Q.40 Whichofthefollowing statement is wrong:
(A)Allcarbonylcompounds ofthegeneralstructure
O
|
|
R
C
CH3 
 give apositive iodoformtest
(B)Allsecondaryalcohols give iodoformreaction
(C)Alkanols ofthe structure CH3CH(OH) – R (where R = H, alkylor aryl) give iodoformreaction.
(D) Theonlyaldehyde giving iodoformreactionis acetaldehyde.
Q.41 A 
 


Br
O
CHBr3
HereAis nothing but:
(A) Isopropylalcohol (B)Methanol (C) Ethanoic acid (D) n-Butylalcohol
Q.42
3
5
2
NH
.
liq
OH
H
C
/
Na



 
 [A] product is :
(A) (B) (C) (D)
Q.43 The appropriate naming for the secondstep inthe haloformreaction is:
(A) Halogenation (B) Dehydrohalogenation
(C) Reduction (D) Dehydrogenation
Q.44 Whichproduct is obtained whenbleaching powder is distilled withacetone:
(A) CCl4 (B) CHCl3 (C) CH2Cl2 (D) CH3Cl
Q.45 What willbe the reductionproduct offollowing reactions:
(A) CH2Cl2, CH3Cl, CH4 (B) CH4, CH3Cl, CH2Cl2
(C) CH3Cl, CH2Cl2, CH4 (D) CH3Cl, CH4, CH2Cl
Q.46 Fe/HClreduction of‘pyrene’(CCl4)gives:
(A) CH4 (B) CH2Cl2 (C) CH3Cl (D) CHCl3
Q.47 Additionofbromine onpropene inthe presence ofbrine yields a mixture of:
(A) CH3CHClCH2Br and CH3CHBrCH2Cl (B) CH3CHClCH2Br and CH3CHBrCH2Br
(C) CH3CHClCH2Cl and CH3CHBrCH2Br (D) CH2CHClCH2Cl and CH3CHBrCH2Cl
Q.48 is converted into by:
(A) (i) CH3– MgI, H3O+ (ii) H2SO4, , (iii) HBr, R2O2
(B) (i) CH3– MgI, H3O+ (ii) H2SO4,  , (iii) HBr
(C) (i) CH3– MgI, H3O+ (ii) HBr
(D) (i) HBr, R2O2 (ii) CH3– MgI, H3O+
Q.49 To formMalonicacid, byshortest possible route, we have to start a reactionfrom:
(A)Ethyledine chloride (B) Methylchloride (C) Methylene chloride (D) Chloro ethan
Q.50 Frankland reagent is:
(A)Dialkyllithium (B)DialkylZinc (C)Dialkylmagnesium (D)Dialkylaluminium
EXERCISE–I (B)
(Choose the correct option. One or more than one are correct)
Q.1 Inthegivenreaction:


 2
Br [X]
[X]is:
(A) (B) (C) (D)
Q.2 Consider thefollowing statements?
(A) CH3–CH2–CH2–I willreact more readilythan (CH3)2 CHI for SN2reactions.
(B) CH3–CH2–CH2–Cl will react more readily than CH3–CH2–CH2–Br for SN2reaction.
(C) CH3–CH2–CH2–CH2–Br will react more readilythan (CH3)3C–CH2–Br for SN2 reactions
(D) CH3–O–C6H5–Br willreact more readilythan NO2–C6H5–CH2Br for SN2reaction
Q.3 Asolutionof(R)-2-iodobutane, [] =–15.9°inacetone istreated withradioactive iodied, until1.0% of
iodobutane contain radioactive iodine, the specific rotation of recovered iodobutane is found to be
15.58°, whichstatement is correct about above information.
(A) It hasopticalpurity96% (B) % ofR in solutionis 99%
(C) Racemicmixture is 2% (D) Finalsolutionis dextrorotatory
Q.4 Whichare possibleproducts in following



 

O
Ag
moist 2
(A) (B) (C) (D)
Q.5 In which product formation takes place accordingto Hoffmann's rule
(A)
Br
|
CH
CH
CH
CH 3
2
3 





 


K
O
u
B
t

(B)
Br
|
CH
CH
CH
CH 3
2
3 





 


K
O
CH
CH 2
3

(C)


 
 H
O

(D)
2
3
3
2
3
)
CH
(
S
|
CH
CH
CH
CH




 

H
O

Q.6 A + B



 

O
H
)
ii
(
O
Et
)
i
(
3
2
Alcohol
Acetone
CrO
H 4
2


 
 Ketone
Ketone is ifAis grignard reagent, then
(A)Aisisobutylmagnesiumbromide (B) B is
3
3
CH
|
O
CH
CH
CH 


(C) B is CHCOCl
CH
|
CH
3
3
 (D)Ais isopropylmagnesiumiodide
Q.7 
 

hv
,
Br2
(A) Br
CH
CH
CH
|
CH
2
3
3

 (B) 3
3
3
CH
CBr
CH
|
CH


(C) CH3CH2CH2Br (D) 3
3 CH
CH
CH
|
Br


Q.8 Select the correct statements fromfollowing
(A) CH3CH2CH2I willreact more readilythan (CH3)2CHI for 2
N
S
(B) CH3CH2CH2Clwillreact more readilythan CH3CH2CH2Br for 2
N
S
(C) CH3CH2CH2CH2Br willreact more readily than (CH3)2CH–CH2Br for 2
N
S
(D) CH3–O–C6H4–CH2Br willreact more readily than NO2–C6H4–CH2Br for 2
N
S
Q.9 Whichofthe following willreact withAcOAg
(A) R–NH2 (B) R–OTs (C) R–N3 (D) R–Br
Q.10 Consider thegivenreaction
)
S
(
H
C
|
OTs
C
H
|
CH
5
2
3

 
 

NaCN
3
2
3
CH
|
CN
CH
CH
CH 
whichoffollowing statements are correct for above reaction.
(A) Product formationtakes place due to the breaking ofO–Ts
(B) The reaction is 2
N
S
(C) The reaction is 1
N
S
(D) Configuration ofproduct is (R)
Q.11 Benzoylchloride isless reactive thanacetylchloride for nucleophilic acylsubstitution reactionbecause
(A) 
C
||
O
group ofbenzoylchloride is inconjugationwithbenzene ring. This makes benzoylchloride
more stablethan acylchloride.
(B) CH3– group ofacetylchloride make C–Clbond stronger due to the +I effect.
(C) C6H5– group of benzoyl chloride make C–Clbond weaker due to +R effect.
(D) Carbonylcarbon in benzoylchlorideis less electrondeficient thanacetylchloride
Q.12 Brominationcantake place at
4
CCl
hv
/
NBS


 

(A) 1 (B) 5 (C) 3 (D) 4
Q.13 Whichoffollowingwillgivesyn-elimination
(A) CH3CH2CH2–OCOCH3 (B)
Cl
|
CH
CH
CH
CH 3
2
3 
(C)
S
|
|
CH
S
C
O
CH
CH
CH 3
2
2
3 


 (D)
3
2
2
3
3
CH
|
O
N
CH
CH
CH
|
CH

 
Q.14 Which offollowing are correct for givenreaction



(A) Major product ofreaction is
(B) Major product is
(C) The reactionis thermaleliminationreaction
(D) The reactionis cyclic E2 reaction
Q.15 Haloformreactionis givenby
(A)All2° alcohol (B)Allmethylketones
(C)Allthe compounds having
O
|
|
C
CH3 
 group (D) Chloral
Q.16 Identifythecompounds that willundergo NGP reaction
(A) CH3CH2–S–CH2CH2Br (B) CH3–NHCH2CH2CH2Br
(C)

O
Br
|
|
O
C
CH
CH3 

 (D) CH3–O–CH2CH2CH2Br
Q.17 Whichalkylhalide undergo E2 elimination
(A) (B)
(C) (D)
Q.18 3-Phenyl-3-pentanolcanbe prepared fromgrignard reagent & other component which can be
(A) 3-pentanone (B) Ethylbenzoate (C) Ethylphenylketone (D)Propanoylchloride
Q.19 Inwhichoffollowing reactioninvertedproduct willobtained.
(A) SN1 (B) SN2 (C) NGP
N
S (D) SNi
Q.20 Rate ofSN2 willbe negligible in
(A) (B) (C) (D)
Q.21 SN1 & SN2 is not favourable in
(A) H2C = CH–Cl (B) Ph–CH2–Cl (C) Ph–Cl (D) H2C=CH–CH2–Cl
Q.22 SN1 & SN2 product are same in (excluding stereoisomer)
(A) (B) (C) (D)
Cl
CH
|
|
CH
CH
CH
Ph
3
3



Q.23 Rate of SN2 depends on
(A) Conc ofNucleophile (B) Conc ofsubstrate
(C) Natureofleaving group (D) Natureofsolvent
Q.24 G 
 

NaOI yellow solid
G can be
(A)
O
|
|
OCH
C
CH 3
3 
 (B)
O
O
|
|
|
|
CH
C
CH
C
CH 3
2
3 



(C) CD3COH (D)
Q.25 Match the List I (reaction) withList II (reaction intermediate)and select the correct answer usingthe
codes givenbelow the Lists.
List I List II
(A) CF3–CHCl2 


 


/
KOH
.
alc CF2 = CCl2 (1) Transitionstate
(B)
3
3
3
CH
|
OH
C
CH
|
CH

 



H
3
2
3
CH
|
CH
C
CH 
 (2) Carbocation
(C) CH3–CH2–Br



 
 KOH
.
alc
CH2=CH2 (3) Carbanion
(D)
3
3
3
CH
|
CH
C
CH
|
Br

 


 


/
KOH
.
aq
3
2
3
CH
|
CH
C
CH 
 (4) Free radical
Q.26 Match theList I withList II and select the correct answer usingthe codes givenbelow the Lists.
List I List II
(A) E1CB (1) QuaterneryAmine oxide
(B) Saytzeffalkene as major product (2) Xanthate
(C) E2 (3) 3
2
3 CH
CH
CH
CH
|
Cl



(D)EC (4)
F
|
CH
CH
CH
H
C 3
2
5
6 


Q.27 MatchList I with List IIand select the correct answer fromthe codes given below:
List I List II
(A) CH3–O–SO2CH3 +

O
H
C 5
2 (1) CH3–CH2–PH2
(B) CH3–CH2–I + PH3 (2) CH3–O–C2H5
(C)

 Na
C
HC

+ CH3–CH2–Br (3) CH3–O–CH3
(D) CH3–Cl + CH3–

O (4) CHC–CH2–CH3
Q.28 MatchList-I withList-II forgiven 2
N
S reaction&select the correct answerfromthe codesgivenbelow
Z–CH2Br +

O
CH3
 Z–CH2–OCH3 +

Br
List-I List-II
(A) H– (P) 0.1
(B) CH3– (Q) 3
(C) C2H5– (R) 1
(D) (S) 100
Q.29 Match List-I & List-II and select correct answer
List-I List-II
(A) R–MgX + HCHO Adduct 
 


O
H3 (P) Ketone
n-carbon
(B) R–MgX + (CH2)2O Adduct 
 


O
H3 (Q) 1°Alcohol(n + 1) carbon
n-carbon
(C) R–MgX + CO2 Adduct 
 


O
H3 (R)Acid (n+ 1) carbon
n-carbon
(D) R–MgX + Ph–CN Adduct 
 


O
H3 (S) 1°Alcohol(n + 2) carbon
Q.30 Matchthe following
List-I List-II
(A)




 


O
CH
CH 2
3 (P) E1
(B)
OD
CH
CH
O
CH
CH
2
3
2
3



 


(Q) E2
(C)
moist
O
Ag2

 
 (R) E1cb
(D) 

 

KOH
.
alc (S) Ec
EXERCISE–II
Q.1 Explain the following giving proper resoning :
(i) Treatment of1,1-dimethyloxirane withsodiummethoxideinmethanolgives primarilyone product.Also
identifythe product giving its IUPAC name
(ii) Trimethylamine reacts with alkyl iodide (RI).As the reaction proceeds the reaction rate abnormally
increases, inspite ofdepleting concentrationofreactants.
(iii) Optically active 2-iodo butane on treatment with NaI*/Acetone gives a product which do not show
opticalactivity.
(iv) Inthe solvent DMSOthe order ofreactivityofhalide ions withmethylbromide is F— > Cl— > Br— > I—
opposite to that observed inmethanolsolution.
(a) (n - C3H7)3N + CH3I  (n – C3H7)3NCH3
+ I—
Relative rate :in hexane, 1 ;in chloroform, 13000
(b) Br— + CH3OTs  CH3Br + TsO—
Relative rates : in methanol, 1;in HMPT, 105.
(v) Although ethers are weaklypolar, are used as solvent ofchoice for Grignard reagents.
(vii) Treatment ofeither CH3– –CH2 Br or CH3–
Br
|
CH – with aqueous HO— gives the
same product.Also write downmechanisminvolved, &IUPAC name ofproduct.
Q.2 On reaction between an alkyl halide and KOH in a mixture of water and ethanol, compare the two
mechanisms SN1 and SN2 :
(a) relative rates ofCH3X, C2H5X, iso-C3H7X & tert-C4H9X
(b) relative rates for RCl, RBr and RI
(c) effect onrate ofa rise in temperature
(d) effect onrateofincreasing water content ofthe solvent.
(e) effect onrate increasing alcoholcontent ofthe solvent.
Q.3 Inthefollowingreactionis carriedout intheweaklyionizingsolvent, acetone (CH3)2C=O. (Bsis brosyl,
p-bromo benzene sulfonyl)
n-C4H9OBs + X—  n-C4H9X + BsO—
The order ofreactivityofhalide ions depends or the salt used on their source :
ifLi+X— is used, I— > Br— > Cl—
if (n-C4H9)4N+ X— is used Cl— > Br— > I—
How do you account for this contrast in behavior ?
Q.4 Whichofthe following is thecorrect method for synthesizing4,4-dimethyl-pent-2-yne, using sodamide
in liquid NH3? Givenreasons.
(i) CH3CCH +
3
3
3
CH
|
Br
C
CH
|
CH

  (ii)
3
3
3
CH
|
CH
C
C
CH
|
CH


 + CH3I 
Q.5 Give the products and find allunknowns.
(a) H2N CH2 CH2 CH2 CH2 Br 

(b)
(c)
Pyridine
TsCl

 
 A
A 
 
NaBr
B
C
Q.6 Find out the unknown alphabets.
(a) + CH3CH2MgBr (1 eq) 
 


O
H3
A
A
(b) 
 


O
H3 B
(2 eq)
(c) H–C
||
O
–OEt + CH3CH2MgBr 
 


O
H3 C
(2 eq)
(d) 
 


O
H3 D
(1 eq.)
Q.7 To prepare
OH
|
H
C
C
|
H
C
5
2
5
2


 byRMgX which is the incorrect pair
(a) MgBr + (C2H5)2CO 
 

O
H2
(b) C2H5MgBr + 
 

O
H2
(c) C2H5MgBr + –COOCH3 
 

O
H2
(d) MgBr + C2H5COOCH3 
 

O
H2
Q.8 KOH
.
alc

 (A) 


 

K
BuO
t
CHBr
–
3
(B)
Q.9
3
2
3
CH
|
Cl
CH
CH
CH
CH
|
Cl



 convert ?
Q.10 What is/are thelimitation in the formationofGrignard reagent byRX + Mg 

 

ether
dry
(a) R should not containanyacidic group
(b) R should not containanyelectronegative group
(c) Alkylhalide shouldnot be vicinaldihalide
(d) Alkylhalide can't be Tertiary.
Q.11 Identifytheunknowns
(a) CH3CH2Cl + I—  A
(b) (CH3)2CH–Br + KOH (aq.)  B
(c) (CH3)3C–Br + KCN (alc.)  C
(d) (CH3)3C–Br + KOH (aq.)  D
(e)
Q.12 Write majorproduct ofthe thefollowing reactions:
(i) ClCH2CH2CH2Br + KCN
heat
EtOH

 
 A
(ii) PhCHO 

 4
SF
B
(iii) BrCH2CH = CHCO2Me
DMF
AgF

 
 C
(iv) EtOH + HI  D
(v) EtOH + HCN  E
Q.13 State at least one characteristic test whichcandistinguish:
(i) C2H5OH from CHCl3
(ii) Halogen atoms present in CHCl3 and CH2 = CHCl
(iii) 1, 1- dibromoethane from1, 2-Dibromethane
(iv) Chlorobenzene fromchlorocyclohexane
(v) o-Chlorotoluene frombenzylchloride
(vi) n-Hexane, CH3CH = CHCl, CH2= CHCH2Cl and CH3CH2CH2Cl
Q.14 CH3–CH2I reacts more rapidly with strong base incomparison to CD3CH2I
Q.15 2-chloro-3-methylbutane ontreatment withalcohoilc potashgives 2-methylbutene-2as major product.
Q.16 Iodoformgives precipitate withAgNO3 onheating while CHCl3 does not.
Q.17 Hydrogen atomofchloroformis definatelyacidic, but that ofmethane is not.
Q.18 Asmallamount ofalcoholis addedto chloroformbottles.
Q.19 Treatment of Me3CCH = CH2 and Me3CCHOHMe with concentrated hydrochloric acid gives the
same two isomeric alkylchlorides what are these two products.
Q.20 Iodine reactswith alcohols to give alkyliodine onlyinpresence ofphosphorous.
Q.21 KCN reacts with R – I to give alkylcyanide, whileAgCN results in isocyanide as major product.
Q.22 The carbocation F3C –

C < is unstable whereas carbocation F3C+ is more stable.
Q.23 Drygaseous hydro halogen acid and not their aqueous solutions are used to preparealkylhalides from
alkenes.
Q.24 RClis hydrolysed to ROH slowlybut reaction fastens onaddition ofKI.
Q.25 The mechanism ofdecomposition ofMe3 S+ OH– is SN2 whereas of Me3S+ I– is SN1.
Q.26 Alkalinehydrolysisofbenzylchloridein50%aqueousacetoneproceedsbybothSN2andSN1mechanism,
when water is used as solvent, mechanismwas now mainlySN1.
Q.27 Ethanolis less reactive than methanolas wellas isopropylalcohols whentreated withdryHClgas.
Q.28 AnhydrousAlCl3 is usedas a catalyst infriedelcrafts alkylation.
Q.29 Arrange following compoundsaccording to their reactivitywithalc silver nitrate.
t-Butylchloride, sec butylchloride and CCl4.
Q.30
(a)
(b)
What are (A) and (B) explaingiving their stereochemistry.
Q.31 n-C10H21Br + HC CNa  A 

 
  Li
Bu
n B
5-methyl-1-hexene + HBr (peroxides)  C 
B
D 



 
 .
cat
s
'
lindlar
/
H2
E 




 
 acid
benzoic
peroxy
F
Q.32 Complete the followingbyproviding (A), (B), (C) and (D):
(i) CH3CH2CH2OH 
 
 3
PBr
(A) 

 

KOH
.
Alc
(B) 
 

HBr
(C) 
 
 3
NH
(D)
(ii) CH3CH2CH2I 

 

KOH
.
Alc
(A) 

 


O
H
/
H 2 (B) 
 
 2
SOCl
(C)
4
LiAlH
H

 (D)
(iii) CH3CH2CH = CH2
Light
NBS

 
 (A) 

 

KOH
.
Alc
(B) 
 

HBr
(C)
(iv) CH3CH2MgBr 



 

O
H
/
CHO
CH 2
3 (A) 
 

HBr
(B) 

 

KOH
.
Alc
(C)
Q.33 Carryout following conversions.
(a) 3
3 CH
CH
CH
|
Cl

 — CH3–CH2–CH2–Cl without using peroxide
(b) CH3–CH2–CH2–Cl —
Cl
|
CH
CH
CH 3
3 
 insingle step
(c) — in three steps only
(d) — in three steps only
(e) Cl
C
CH
Ph
||
O
2 

 — Ph – CH2 – Cl
(f) Ph – CH2 – Cl — Cl
C
CH
Ph
||
O
2 


EXERCISE–III
Q.1 Aprimaryalkylhalide (X) C4H4Br reacted withalcoholic KOH to give(Y). (Y) reacts withHBr to give
(Z) anisomer of(X). Onreacting withalkalimetalsuchas sodium/dryether gives (S) C8H18 whichwas
different fromthe compound produced when n-butylbromidewas treated with Na. What (X), (Y), (Z)
and (S).
Q.2 On electrolysis anaqueous ethanoilc solution ofsodiumchloride gives sweet smelling liquid (X). (X)
gives isocyanide test and condenses withacetone to fromhypnotic(Y). What are (X) and (Y)?
Q.3 The alkyl halide C4H9Br (A) reacts with alcoholic KOH and gives an alkene (B), which reacts with
bromide to give dibromide (C). (C) is transformed with KOH & sodamide to gas (D) which forms a
precipitate whenpassedthroughanammonicalsilvernitrate solution. Give thestructureformulae ofthe
compounds (A), (B), (C) and (D) and explain reactions involved.
Q.4 An unsaturated hydrocarbon (A) C6H10 readily gives (B) on treatment with NaNH2 in liquid NH3.
When(B)isallowedto reactwith1-chloropropane,acompound(C)isobtained. Onpartialhydrogenation
inthe presence ofLindlarcatalyst, (C) gives (D), C9H18. Onozonolysis (D) gives2, 2-dimethylpropanal
and 1-butanal. Give structures of(A), (B), (C) and (D) withproper reasoning.
Q.5 One mole of each bromoderivative (A) and NH3 react to give one mole ofan organic compound (B).
(B) reacts with CH3I to give (C). Both (B) and (C) react with HNO2 to give compounds (D) and (E),
respectively. (D) onoxidation and subsequent decarboxylation gives 2 -methoxy-2-methylpropane.
Give structuresof(A) to (E) with proper reasoning.
Q.6 A chloro derivative (A) on treatment with zinc-copper couple gives a hydrcarbon with five carbon
atoms. When'A'is dissolved in eitherand treated with sodium, 2,2,5,5-tetramethylhexane is obtained.
What is theoriginalcompound 'A'?
Q.7 Aprimaryalkylhalide (A) C4H9Br reacted withalcoholic KOH to give(B). (B) reacts withHBr to give
(C) an isomers of (A). (A) on reacting with sodium gives (D) C8H18 which was different from the
compound produced whenn-butylbromide was treated withNa.What are (A), (B), (C) and (D).
Q.8 One mole ofa hydrocarbon (A)reacts with1 mole ofbromine giving a dibromo compound C5H10Br2.
(A) ontreatment withcold dilute alkaline KMnO4 solutionformsa compound C5H12O2. on ozonolysis
(A) givesedquimolar quantities ofpropanone and ethanal. Deduce structure of(A).
Q.9 A hydrocarbon (A) was found to contain 85.7% carbon and 14.3% H. This compound consumes 1
molar equivalent ofhydrogento give asaturated hydrocarbon. 1g of(A) just decolourised38.05of5 %
solution byweight ofBr2 in CCl4. Compound (A) on oxidation withconc. KMnO4 gave a compound
(C), C4H8O and(B) acetic acid. Compound (C) caneasilybe prepared bythe actionofacidic aqueous
mercuric sulphate on 2-butyne. Deduce (A), (B) and (C).
Q.10 When a hydrocarbon (A) is treated with excess of hydrogen chloride, a dihalogen derivative (B) is
obtained. The compound(B) is treated separatelywithaqueous and alcoholic KOHto give compounds
(C) and (A) respectively both having three carbon atoms. Compound (C) does not reduce Tollen's
reagent and compound (A) give white precipitate with ammonical silver nitrate.Assign structures to
compounds (A) to (C).
Q.11 An organic compound (A) C7H15Clontreatment withalcoholiccaustic potashgives ahydrocarbon(B)
C7H14. (B) ontreatment withozone andsubsequent hydrolysis gives acetoneand butyraldehyde. What
are (A) and(B). Explain reactions.
Q.12 A dihalogenderivative (A) ofa hydrocarbon having two carbonatoms react with alcoholicpotashand
forms anotherhydrocarbon whichgives ared precipitate withammonicalcuprous chloride. Compound
(A) gives an aldehyde when treated with KOH (aq). What is (A)?
Q.13 Awhite precipitate was formed slowly whenAgNO3 was added to a compound (A) with molecular
formula C6H13Cl. Compound (A)ontreatment withhot alcoholic KOH gave a mixtureoftwo isomeric
alkenes (B) and (C) having formula C6H12. The mixture of(B) and (C) onozonolysis furnished four
compounds (i) CH3CHO, (ii) C2H5CHO, (iii) CH3COCH3, (iv) (CH3)2CH.CHO
What are (A), (B) and (C).
Q.14 0.369 g ofa bromo derivative ofa hydrocarbon(A) when vaporizedoccupied 67.2 mLat NTP. (A) on
reactionwithaqueousNaOHgives(B).(B)whenpassedoveraluminaat 250°Cgivesaneutralcompound
(C) whileat 350°C it givesa hydrocarbon(D). (D)whenheated withHBrgives anisomer of(A). When
(D) is treated with dil. H2SO4 , (E) is obtained. Identify(A) to (E) and explain the reactions.
Q.15 An organic compound (X) on analysis gives 24.24 % C, 4.04% H. Further sodiumextract of1.0 g of
(X) gives 2.90 g ofAgClwith acidifiedAgNO3 solution. The compound (X) maybe represent bytwo
isomericstructures(Y)and(Z).(Y)ontreatmentwithaqueousKOHsolutiongivesadihydroxycompound,
while (Z)on similar treatment givesethanal. Find out (X), (Y) and (Z).
Q.16 Achloro compound (A) showed thefollowing properties :
(i) Decolourized bromine inCCl4
(ii) Absorbed hydrogencatalytically.
(iii) Gave a precipitate withammonicalcuprous chloride
(iv) When vaporised 1.49 g of (A) gave 448 mLofvapours at STP.
Identify(A)and write downtheequations ofreactions.
EXERCISE–IV (A)
Q.1 Chlorinationoftolueneinthe presenceoflight and heatfollowedbytreatment withaqueousNaOH gives
(A) o-cresol (B) p-cresol
(C) 2,4-dihydroxytoluene (D) Benzoic acid
Q.2 Aryl halidesarelessreactivetowardsnucleophilicsubstitutionreactionascompared to alkyl halidesdueto
(A) Theformation of lessstablecarbonium ion (B) Resonancestabilization
(C) Theinductiveeffect (D) sp2 hybridised carbonattached to the halogen
Q.3 1-Chlorobutane on reactionwithalcoholic potash gives:
(A) 1-butene (B) 1-butanol (C) 2-butene (D) 2-butanol
Q.4 The products ofreaction ofalcoholicAgNO2 withethylbromide are
(A)Ethane (B)Ethylnitrite (C) Nitroethane (D) Ethylalcohol
Q.5 When nitrobenzene is treated with Br2 in presence ofFeBr3 the major product formed is:
m-bromonitrobenzene. Statementswhich are related obtainthe m-isomer are
(A) The electrondensityon meta carbonis more than on ortho and para position
(B) The intermediate carbonium ion formed after initial attack of Br+ at the meta position is least
destabilized.
(C) Loss ofaromaticitywhen Br+ attacks at the ortho and para position and not at meta position
(D) Easier loss ofH+ to regain aromaticityfromthe meta positionthanfromotho andpara positions.
Q.6 Arrange the followingcompounds inorder ofincreasing dipole moment
Toluene m-dichlorobenzene o-dichlorobenzene p-dichlorobenzene
I II III IV
(A) I < IV < II < III (B) IV < I < II < III (C) IV < I < III < II (D) IV < II < I < III
Q.7 In the reaction ofp-chloro toluene with KNH2 in liq. NH3, the majorproduct is:
(A)o-toluidine (B)m-toluidine (C) p-toluidine (D)p-chloraniline
Q.8 (CH3)3CMgClreaction with D2O produces:
(A) (CH3)3CD (B) (CH3)3OD (C) (CD3)3CD (D) (CH3)3OD
Q.9 Benzylchloride (C6H5CH2Cl) canbe prepared fromtoluenebychlorination with:
(A) SO2Cl2 (B) SOCl2 (C) Cl2 (D) NaOCl
Q.10 Toluene, when treated with Br2/ Fe, gives p-bromotoluene as the major product, because the CH3
group
(A) is para directing (B) ismeta directing
(C) activates the ring byhyperconjugation (D) deactivatesthe ring
Q.11 The order ofreactivityofthe following alkylhalidesfor a SN2reaction is:
(A) RF > RC > R–Br > R–I (B) R–F > R–Br > R–Cl > R–I
(C) R–Cl > R–Br > RF > RI (D) R–I > RBr > R–Cl > R–F
Q.12 Identifytheset ofreagents /reaction conditions 'X'and'Y' in the followingset oftransformation:
CH3 – CH2 – CH2Br 

X Product 

Y
Br
|
CH
CH
CH 3
3 

(A) X = dilute aqueous NaOH, 20°C;Y = HBr / acetic acid, 20°C
(B) X = concentrated alcoholic NaOH, 80°C;Y = HBr/ acetic acid 20°C
(C) X = dilute aqueous NaOH, 20°C; Y = Br2 / CHCl3, 0°C
(D) X = concentrated alcoholic NaOH, 80°C;Y = Br2/CHCl3, 0°C
Q.13 CH3MgBr + Ethylester  whichcan be formed as product.
(excess)
(A) (B)
(C) (D)
Q.14 Matchthefollowing:
ColumnI ColumnII
(A) CH3–CHBr–CD3 on treatment with alc. KOH gives (P) E1 reaction
CH2=CH-CD3 as a major product.
(B) Ph – CHBr - CH3 reacts faster than Ph-CHBr-CD3. (Q) E2 reaction
(C) Ph-CH2-CH2Br on treatment with C2H5OD/C2H5O– (R) E1cb reaction
gives Ph-CD=CH2 as the major product.
(D) PhCH2CH2Br and PhCD2CH2Br react with same rate. (S) First order reaction
EXERCISE–IV (B)
Q.1 Fillinthe blanks:
(a) Butan nitrile canbe prepared byheating _____with alcohalic KCN.
(b) Amongst three isomersofnitrophenol, the onethat is least soluble in water is_____
Q.2 Identifythemajor product inthefollowing reactions :
(i) 3
2
5
6 CH
CH
CH
H
C
|
Cl






 

KOH
alcoholic
? 

HBr
?
(ii) C6H5COOH + CH3MgI  ? + ?
Q.3 AnalkylhalideX offormula C6H13Clontreatment withpotassiumtertiarybutoxidegives two isomeric
alkenesYandZ (C6H12). Bothalkenesonhydrogenationgive2,3–dimethylbutane. Predict the structures
ofX, Yand Z.
Q.4 Predict the structure ofthe intermediates/productsin the following reactionsequence –
Acetone
NaI


 C
Q.5
(a) CHCl
CH
H
C
|
H
C
2
5
6
5
6
Heat
KOH
Alcohalic




 
 A+ BWrite structures of(A) and (B).
(b) (CH3)2CHOCH3
Heat
)
excess
(
HI



 
 A+ B Write structures ofAand B.
Q.6 Complete thefollowing reaction withappropriatestructures ofproducts/reagents.


 2
Br (A)
I
CH
)
II
(
.)
equi
3
(
NaNH
)
i
(
3
2





 
 (B)
Q.7 What would be major product?
3
2
3
3
CH
|
Br
CH
C
CH
|
CH


e
temperatur
low
at
OH
H
C


 
 5
2
?
Q.8 How would you synthesis 4 methoxyphenolfrombromobenzene in NOT more thanfive steps? State
clearlythe reagents used in eachstep and show the structures ofthe intermediate compounds in your
synthetic scheme.
Q.9 An alkeneA(C16H16) onozonolysis give onlyoneproduct B (C8H8O). Compound B onreaction with
NaOH/I2 yields sodiumbenzoate. Compound B reacts with KOH/NH2NH2 yielding a hydrocarbon C
(C8H10). Write the structure ofcompound B and C. Based on this information two isomeric structures
can be prepared for alkene A. Write their structures and identify the isomer which on catalytic
hydrogenation (H2/Pd–C) gives a racemic mixture.
Q.10 Give major productsA, B, C and D in following reaction sequence.
DMF
KCN

 
 (A)





 

/
PhCHO
)
ii
(
EtOH
/
NaOEt
)
i
(
(B) 
 


O
H3
(C)
(D)
ANSWER KEY
EXERCISE–I (A)
Q.1 D Q.2 A Q.3 C Q.4 D Q.5 A Q.6 D Q.7 A
Q.8 B Q.9 C Q.10 C Q.11 C Q.12 C Q.13 A Q.14 D
Q.15 C Q.16 B Q.17 A Q.18 D Q.19 C Q.20 D Q.21 B
Q.22 C Q.23 D Q.24 C Q.25 D Q.26 B Q.27 B Q.28 A
Q.29 B Q.30 C Q.31 B Q.32 B Q.33 C Q.34 C Q.35 A
Q.36 A Q.37 C Q.38 C Q.39 A Q.40 B Q.41 A Q.42 A
Q.43 A Q.44 B Q.45 A Q.46 D Q.47 B Q.48 A Q.49 C
Q.50 B
EXERCISE–I (B)
Q.1 D Q.2 A,C Q.3 B,C Q.4 A,B
Q.5 A,C,D Q.6 A,B,C Q.7 B Q.8 A,B,D
Q.9 B,C,D Q.10 B,D Q.11 A,D Q.12 A,C,D
Q.13 A,C,D Q.14 A,C,D Q.15 B,D Q.16 A,B,C,D
Q.17 A,B Q.18 A,B,C Q.19 A,B Q.20 A,B,C
Q.21 A,C Q.22 B,C Q.23 A,B,C,D Q.24 B,C,D
Q.25 A  3, B  ,C  1,D  2 Q.26 A  4, B  3,4, C  3, D  1,2
Q.27 A  2, B  1, C  4, D  3 Q.28 (A) – S; (B) – Q; (C) – R; (D) – P
Q.29 (A) – Q; (B) – S ; (C) – R; (D) – P Q.30 (A) – Q; (B) – R ; (C) – P; (D) – Q
EXERCISE–II
Q.1 (i)
OH
|
CH
CH
CH
|
|
CH
O
CH
2
3
3
3



attack take place on less stericallycarbon
Q.4 (ii)
Q.5 (a)
(c) (A) Me
CH
C
Me
|
Me


 , (B)
OEt
|
Me
CH
C
Me
|
Me
2 

 , (C)
I
|
Me
CH
C
Me
|
Me
2


(d) (A) , (B) , (C)
Q.6 (a) (b) (c) Et
CH
Et
|
OH

 (d)
Q.7 (d) Q.8 A  B 
Q.9 A 
3
2
3
CH
|
CH
CH
CH
CH 

 B 
C
|
Cl
C
C
C
C 



Conversion (1) NaNH2 (2) H2/Pd BaSO4
Q.10 (a) & (c)
Q.11 (a) A Et – I (b) B  OH
CH
CH
|
CH
3
3

 (c) Me2C=CH2
(d) Me2C=CH2 (e) &
OH
|
CH
OH
Me
|
OH
2


Q.12 The mechanismof
(i) ClCH2CH2CH2CN (ii) PhCHF2
(iii) FCH2CH = CHCO2Me (iv) EtI
(v) no reaction
Q.13 (i)Chloroformrespondscarbylamine test while ethylalcoholdoes not. Carbylaminetest-Thecompound
is heated withaniline and alcoholic causticpotash-an obnoxious smellofphenylisocyanide (C6H5NC)
is produced.
(ii) Chlorine atoms ofchloroformcanbeeasilyreplaced by– OH groups on treatment with NaOH. Hence
chlorine atomscome inthe formofsodiumchloride. The solution thus whentreatedwithsilver nitrate
solutiongiveswhite precipitate ofsilverchloride. Chlorine atominvinylchloride is not readilyreplaced
byNaOH, hence it does not give precipiatet withAgNO3 solution.
(iii) The two compounds are hydrolysed withaqueous NaOH when1, 1-dibromoethane formacetaldehyde
while 1, 2-dibromoethane gives glycol.
(iv) Chlorineatominchlorobenzene is verylessreactive, whilechlorineincyclohexylchlorideisveryreactive.
Hence the two can be differentiated as above in (ii)
(v) Apply test (ii) as above; when benzylchloride gives white precipitate withAgNO3 solution, while O
chlorotoluene doesnot give precipitate.Alternately, the compounds are oxidisedwheno chlorotoluene
give o-chlorobenzoicacid whenbenzylchloride gives benzoic acid (havingnon chlorine.)
(vi) n - Hexane does not respond Cl– iontest even after fusionwith Na and treatment with acidicAgNO3.
the remaining three compounds are distinguished bytheir reactivitywithalcoholicAgNO3 solution.
(a) CH3 – CH = CHCl (a vinylic chloride) does not react with alc.AgNO3 evenon heating
(b) CH2 = CHCH2Cl(an allylic chloride) is the most reactive and precipitatesAgClin the cold.
(c) CH3–CH2–CH2–Clgives precipitate ofAgClon warming withAlc.AgNO3
Q.14 TheeliminationofHI (orDI) inpresence ofstrongbaseshows E2elimination. Therate determiningstep
involves breaking up of C – H (or C–D) bond. the C–D bond being stronger than C–H and thus
elimination is faster in case ofCH3 – CH2I.
Q.15
Cl
CH
|
|
CH
CH
CH
C
H
3
3
3


 

 

)
alc
(
KOH
or
min
major
CH
CH
|
|
CH
CH
CH
CH
CH
CH
C
CH
3
3
2
3
3
3







Elininationoccursaccording to saytzeffrule. The major product isone which involves eliminationofH
fromless hydrogenated carbon.
Q.16 C–I bond being less stable than C–Cl bond and thus on heating heterolytic cleavage of C –I form I–
whichgives yellowprecipitate withAgNO3
Q.17 Due to three electronegative chlorine atoms present on carbon, the latter acquires a partial positive
charge due to –I effect ofchlorine with the result it tends to attract electrons ofthe C–H bond towards
itself. Hence the removalofhydrogen atomas proton becomes easier.
Q.18 Alcoholacts asnegative catalyst for oxidationofchloroform.Also it reacts withCOCl2 to giveharmless
diethylcarbonate.
Q.19 Carboniumions canundergo rearrangement fromlessstable to more stable ones. Bothcompounds give
the same carboniumioninitially. Hence
Me3CCHOHMe O
H
)
ii
(
H
)
i
(
2


 


HMe
C
C
Me
|
Me
2

 
 


H
Me3CCH = CH2Cl–
rearrangement
Me3CCHClMe Me2 2
CHMe
C





Cl
Me2CClCHMe2
Bothgivethesametwoisomericchlorideinthesameproportions, withthetertiarychloridepredominating.
Q.20 Phosphorus reacts with I2 to give PI3 whichreplaces OH group ofalcoholto produce R – I
2P + 3I2  2 PI3
3R OH + PI3  3RI + H3PO3
Q.21 KCN is an ionic compound [K+(:C N:)–] in which both C and N carry a lone pair electron. Carbon
carrying lone pairofelectrons is morereactive and thus alkylattacks carbonto givealkylcyanideAgCN
being covalent hasAg– CN : structure with lone pair on N thus R attacks N atom and R–N

 C is
formed.
Q.22 The strong – I.E offluorine atom in F3C –

C < produces partial +ve charge on C atom ofCF3 which
ultimatelyincreases + ve charge on2nd carbonatomto destabilize it
F
C
F
F









In F3C+, the unsharedpair ofelectrons in the p orbitals ofeachofthe fluorine atomareshifted to C+ via
p–p orbitaloverlapping and thus stablizing F3C+ ion
Q.23 Drygaseoushydro halogenacidsarebetterelectrophile.Also inaqueoussolutionH2Oactingasnucleophile
mayproduce alcohol.
Q.24 KI reacts with RCl to form RI. This RI molecule now hydrolysed easily to give ROH because alkyl
iodide are more reactive than alkylchloride.
RCl + KI  RI 
 

HOH
ROH (more fast)
Q.25 Themorepronouncedthenucleophilicactivityoftheattackingreagent,thenthemoretheSN2mechasnism
will be favoured. Since in SN1 mechanismthe raegent doesnot enter into the rate determining step of
ionisationHoweverit canalso beexpected that asthenucleophilicactivtiyisso slowthat themechanism
willchange fromSN2 to SN1
Q.26 The dielectric constant of water is greater than that ofaqueous acetone, and so ionisation of benzyl
chloride isfacilitated.
Q.27 Onmoving from3°to 1°alcoholrateofSN2reactiondecreasesand reaches to minimumand mechanesm
changes fromSN2 to SN1, Thenrate ofSN1 rate ofreaction increases.
Q.28 AnhydrousAlCl3 is usedas a catalyst infriedelcrafts alkylation.
Q.29 tert-Butylchloride, sec butylchloride and CCl4 withalc. silver nitrate
Me3C – Cl > CHCl > CCl4
Q.30 (a) A B  C  D 
E  F  G  H 
I 
(b) (A) , (B)
Q.31 A  C10H21–CCH B  CLi
C
H
C 21
10 



C 
C
|
Br
C
C
C
C
C
C 





D 
3
3
4
2
21
10
CH
|
CH
CH
)
CH
(
C
C
H
C 



 E 
3
3
4
2
21
10
CH
H
H
|
|
|
CH
CH
)
CH
(
C
C
H
C 




F 
H
O
H

/

/
CH
CH
)
CH
(
C
C
H
C
|
CH
3
4
2
21
10
3





Q.32 (i)A, CH3CH2CH2Br ; B, CH3CH = CH2 ; C, CH3CHBrCH3; D, CH3CHNH2CH3
(ii) A, CH3CH = CH2; B, CH3CHOHCH3; C, CH3CHClCH3; D, CH3CH2CH2
(iii) A, CH3CHBrCH = CH2; B, CH2=CH–CH=CH2; C, CH3CHBrCH=CH2& CH3CH = CH–CH2Br
(iv) A, CH3CH2CHOHCH3; B, CH3CH2CHBrCH3; C, CH3CH = CH – CH3
EXERCISE–III
Q.1
)
X
(
CH
|
Cl
CH
CH
CH
3
2
3 


)
Y
(
CH
|
CH
C
CH
3
2
3


)
X
of
isomer
(
)
Z
(
propane
methyl
2
Bromo
2
CH
|
CH
C
CH
|
Br
3
3
3





(CH3)2CH – CH2–CH2–CH (CH3)2
(2,5 –dimethylHexane)
(S)
Q.2 (Y)
Q.3 CH3CH2CH2CH2Br CH3CH2CH = CH2
Br
Br
|
|
CH
CH
CH
CH 2
2
3 


(A) (B) (C)
CH3– CH2– C  CH
(D)
Q.4 (CH3)3C – C  CH (CH3)3C – C C–Na+ (CH3)3C – C  CH2CH2CH3
(A) (B) (C)
(CH3)3C – CH = CHCH2CH2CH3
(D)
Q.5 Br
CH
CH
)
CH
(
C
CH
|
OCH
2
2
3
3
3



 2
2
2
3
3
3
NH
CH
CH
)
CH
(
C
CH
|
OCH



(A) (B)
3
2
2
3
3
3
NHCH
CH
CH
)
CH
(
C
CH
|
OCH


 OH
CH
CH
)
CH
(
C
CH
|
OCH
2
2
3
3
3



(C) (D)
3
2
2
3
3
CH
|
O
N
N
CH
CH
CH
CH
|
OCH






(E)
Q.6 (CH3)3C – CH2Cl
Q.7 Br
CH
CH
CH
|
CH
2
3
3

 CH
C
CH
|
CH
3
3


Br
|
CH
C
C
H
|
CH
3
3
3


(A) (B) (C)
3
2
2
3
3
3
CH
CH
CH
CH
CH
CH
|
|
CH
CH




(D)
Q.8
Q.9 C = CH – CH3 CH3–COOH C = O
(A) (B) (C)
Q.10 CH3– C  CH
Cl
|
CH
C
CH
|
Cl
3
3 

3
3 CH
C
CH
|
|
O


(A) (B) (C)
Q.11
3
3
2
3
3
CH
|
Cl
C
)
CH
(
CH
|
CH

 CH3(CH2)2CH = C (CH3)3
(A) (B)
Q.12 H3C – CHX2 ( X = Halogen)
Q.13
Br
|
CH
CHCH
CH
)
CH
( 3
2
2
3  (CH3
)2
CH CH = CH CH3
C = C
(A) (B) (C)
Q.14 (A) CH3CH2CH2Br , (B) CH3CH2CH2OH, (C) CH3CH2CH2OCH2CH2CH3, (D) CH3–CH=CH2,
(E) CH3CH(OH)CH3
Q.15 (X) C2H4Cl2, (Y) Cl – CH2CH2 – Cl, (Z) CH3CH
Q.16 HC C–CH2– Cl
EXERCISE–IV (A)
Q.1 D Q.2 D Q.3 A Q.4 C Q.5 A,B Q.6 B Q.7 B
Q.8 A Q.9 A,C Q.10 A,C Q.11 D Q.12 B Q.13 D
Q.14 A – Q; B – Q; C – R,S; D – P,S
EXERCISE–IV (B)
Q.1 (a) propylchloride, (b) ortho
Q.2 (i) 3
5
6 CH
CH
CH
H
C 

 ; 3
2
5
6 CH
CH
CH
H
C
|
Br



(ii) C6H5COOMgI + CH4
Q.3 (X):
Cl
|
CH
CH
—
C
CH
|
|
CH
CH
3
3
3
3

 ; (Y) : 3
2
3
3
CH
CH
—
C
CH
|
|
CH
CH

 ; (Z) :
3
3
3
3
CH
CH
|
|
CH
CH
—
C
CH 

Q.4 (NGP due to MeO, so retentionofconfiguration)
Q.5 (a) Cis and trans forms of stibene C6H5CH=CHC6H5 ; (b)
Q.6 (A) 


 

.)
liq
(
NaNH2

 

I
CH3 (B)
Q.7
5
2
3
2
3
3
H
OC
|
CH
CH
C
CH
|
CH


Q.8 pressure
high
NaOH




 

4
2SO
Me





 
 4
2SO
H
.
conc

 

NaOH

 


O
H3
Alternativerout



 
 4
2SO
H
.
conc

 

NaOH
4
2SO
Me


pressure
high
NaOH




 
 
 


O
H3
Q.9 (A) PhC(Me)=C(Me)Ph 


 


 O
H
Zn
O 2
3 (B) Me
PhC
2
|
|
O

3
3 NH
NH
KOH


 
 (C) PhCH2Me
Two isomers ofAare cis and trans
Q.10 (A) ; (B) ; (C) ; (D)

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HALOGEN DERIVATIVES.pdf

  • 1. CONTENTS EXERCISE - I (A) EXERCISE I(B) EXERCISE - II EXRECISE - III EXRECISE - IV(A) EXERCISE IV(B) ANSWER KEY ORGANIC CHEMISTRY HALOGEN DERIVATIVES
  • 2. EXERCISE–I (A) (Choose the correct option. Only one is correct) Q.1 Whichone is liquid at roomtemperature: (A) CH3Cl (B) C2H5Cl (C) CH3Br (D) C2H5Br Q.2 The correct orderofmelting and boilingpoints ofthe primary(1°), secondary(2°) andtertiary(3°) alkyl halides is: (A) P > S > T (B) T > S > P (C) S > T > P (D) T > P > S Q.3 Pick upthe correct statement about alkylhalides: (A) Theyshow H-bonding (B) Theyare soluble in water (C) Theyaresoluble inorganic solvent (D) Theydo not contain anypolar bond Q.4 What wouldbe the product whenneopentylchloride reacts withsodiumethoxide: (A) 2-Methyl-2-butanol (B) Neo pentylalcohol (C) Both 1st & 2nd (D) 2-Methyl-2-butene Q.5 Reduction ofalkylhalide byLiAlH4 is the type ofreaction: (A)Nueleophilicsubstitutionreaction (B) Electrophilicsubstitutionreaction (C) ElectrophilicAdditionreaction (D) None ofthese Q.6 2-methyl butanoic acid is formed bythe reaction CHCl3, NaOH and (A) Propene (B) Ethene (C) 1-Butene (D) 2-Butene Q.7 CCl4 + KOH (excess) end product ofthe reaction is: (A) K2CO3 (B) CO2 (C) C (OH)4 (D) HCOOK Q.8 The yield of alkyl bromide obtained as a result of heating the dry silver salt of carboxyic acid with bromine ifCCl4 is: (A) 1° > 3° > 2° bromides (B) 1° > 2° > 3° bromides (C) 3° > 2° > 1° bromides (D) 3° > 1° > 2° bromides Q.9 Whichofthefollowing statementsis invalid: (A) The more stable the carbocation the faster it is formed (B) Propylcationchanges to more stable isopropylcarbocation by1,2 shift ofa hydrogen (C) Isopropylchloride reacts with sodiumethoxide to form1-ethoxypropane (D) Propylhalidesreacts with sodiumethoxide to form1-ethoxypropane Q.10 Nitrochloroformis prepared bythe actionofchloroformand: (A) Hot aqueous solution ofKNO3 (B) Hot aqueoussolution ofNaNO2 (C) Hot concentrated nitric acid (D) Hot dilute HCl+ aq. NaNO2 solution Q.11 Which ofthe following compounds is most rapidlyhydrolysed bySN1 mechanism. (A) C6H5Cl (B) Cl–CH2–CH = CH2 (C) (C6H5)3CCl (D) C6H5CH2Cl Q.12 CH3MgBr + H C CH CH | | O 2        O H2 product (major), product is (A) 3 2 CH | H C CH CH | OH    (B) OH | CH CH CH CH 3 2    (C) CH3–CH2–CH2–CHO (D) None is correct
  • 3. Q.13 Whichis incorrect about Hunsdicker reaction? (A) OnlyCl2 cangive alkylhalide (B) I2 willgive ester when treated with RCOOAg (C) The reactionproceeds throughfree radical (D) F2 cannot give alkylhalide Q.14 Major product for the reaction hv Br2    is: (A) (B) (C) (D) Q.15 II OH      I OH      B A Steps I and II are (A) both SN1 (B) both SN2 (C) ISN1, II SN2 (D) I SN2, II SN1 Q.16 What areA& B inthe following reaction?      THF / Mg A A Cl NH . aq ) ii ( CHO CH ) i ( 4 3       B (A) & (B) & (C) & (D) None ofthese Q.17 Ester A(C4H8O2) + CH3MgBr      O H3 C4H10O (2 pair) (alcohol) (B) AlcoholB reacts fastest with Lucas reagent. HenceAand B are (A) COH ) CH ( , H C O C CH | | O 3 3 5 2 3    (B) CHOH ) CH ( , H C O C H | | O 2 3 7 3    (C) CHOH ) CH ( , H C O C CH | | O 2 3 5 2 3    (D) COH ) CH ( , H C O C H | | O 3 3 7 3   
  • 4. Q.18 The hydrolysis ofalkylisocyanides (R–CH2–N  C) gives (A) RNHCOOH (B) 2 NH | COOH CH R   (C) RNH2 + HCOOH (D) RCH2NH2 + HCOOH Q.19 What is product ofthe following reaction? O ET Mg 2    ? (A) (B) (C) (D) None ofthese Q.20 Following reactionis:      OH (A) SE2 (B) SN1 (C) SN0 (D) SN2 Q.21 + OH–     2 SN A A Ais: (A) (B) (C) Both (D) None Q.22 CHCl3 + OH–  HCOO– Intermediates ofthis reaction are (A)    3 CCl (B) 2 CCl   (C) both (D) None Q.23 Racemic mixtureis obtained due to halogenation of: (A) n-pentane (B) Isopentane (C) neopentane (D) BothA& B Q.24 For CH3Br + OH–  CH3OH + Br– the rate ofreactionis givenbythe expression: (A) rate = k [CH3Br] (B) rate = k[OH–] (C) rate = k [CH3Br][OH–] (D) rate = k[CH3Br]°[OH–]° Q.25 Whichwillgive white ppt. withAgNO3? (A) (B) (C) (D) BothA& C Q.26 The reaction ofSOCl2 onalkanols to formalkylchlorides gives good yields because (A)Alkylchloridesare immscible with SOCl2 (B) The other products ofthe reaction are gaseous and escape out (C)Alcoholand SOCl2 are soluble in water (D) The reactiondoes not occurs via intermediate formation ofanalkylchloro sulphite
  • 5. Q.27 True about alkylhalides is / are: (A) Tertiaryalkylhalides undergo SN2substitutions (B)Alkyliodides on exposure to sunlight graduallydarken (C)Alkylchlorides do not give beilstein test (D)Anucleophilicsubstitutionis most difficult inalkyliodides Q.28 The product formed whenglycerolreacts with PCl5 is– (A) 1,2,3–trichloropropane (B)Glycero monochlorohydrin (C) Glycero dichlorohydrin (D)Allofthese Q.29 On heating glycerolwith excess amount to HI, the product formed is– (A)Allyliodide (B) Isopropyliodide (C) Propylene (D) 1,2,3–tri–iodopropane Q.30 To prepare 3-ethyl-3-pentanolthe reagents needed are: (A) CH3CH2MgBr + O | | CH CH C CH 3 2 3   (B) CH3MgBr + O | | CH CH C CH CH 3 2 2 3   (C) CH3CH2MgBr + O | | CH CH C CH CH 3 2 2 3    (D) CH3CH2CH2MgBr + O | | CH CH C CH 3 2 3   Q.31 Non-occurence ofthe following reaction Br– + CH3OH  BrCH3 + OH–, is due to (A)Attacking nucleophileis stronger one (B) Leaving group is a strong base (C)Alcohols are not good substrate (D) Hydroxide ions are weak bases Q.32 When ethylbromide is treated withmoistAg2O, mainproduct is: (A)Ethylether (B)Ethanol (C) Ethoxyethane (D)Allofthe above Q.33 When ethylbromide is treated withdryAg2O, mainproduct is: (A)Ethylether (B)Ethanol (C) Ethoxyethane (D)Allofthe above Q.34 OH H C O H C 5 2 5 2       ?Major product is: (A) (B) (C) (D)
  • 6. Q.35     2 Br ?Product is: (A) (B) (C) both(A) & (B) (D) noneofthese Q.36 2 E KOH , alcoholic        A A (A) (B) (C) (D) None is correct Q.37 To remove ‘phosgene’fromchloroform, _________ is added: (A)Ethylamine (B)Ethylchloride (C) Ethylalcohol (D) Ethane Q.38 Agemdichloride is formed inthe reactionexcept: (A) CH3CHO and PCl5 (B) CH3COCH3 and PCl5 (C) CH2 = CH2 and Cl2 (D) CH2 = CHCl and HCl Q.39 O | | CH C CH 3 3   3 2 2 CO Na I     (A)       powder Ag (B)        Hg SO H 4 2 Product A, B & C are: (A) Iodoform,Acetylene &Acetaldehyde (B) Tri. iodomethane, Ethyne &Acetone (C) Iodoform, Ethene&Ethylene glycol (D) Ethene, iodoform&Ethylhydrogensulphate Q.40 Whichofthefollowing statement is wrong: (A)Allcarbonylcompounds ofthegeneralstructure O | | R C CH3   give apositive iodoformtest (B)Allsecondaryalcohols give iodoformreaction (C)Alkanols ofthe structure CH3CH(OH) – R (where R = H, alkylor aryl) give iodoformreaction. (D) Theonlyaldehyde giving iodoformreactionis acetaldehyde. Q.41 A      Br O CHBr3 HereAis nothing but: (A) Isopropylalcohol (B)Methanol (C) Ethanoic acid (D) n-Butylalcohol Q.42 3 5 2 NH . liq OH H C / Na       [A] product is : (A) (B) (C) (D)
  • 7. Q.43 The appropriate naming for the secondstep inthe haloformreaction is: (A) Halogenation (B) Dehydrohalogenation (C) Reduction (D) Dehydrogenation Q.44 Whichproduct is obtained whenbleaching powder is distilled withacetone: (A) CCl4 (B) CHCl3 (C) CH2Cl2 (D) CH3Cl Q.45 What willbe the reductionproduct offollowing reactions: (A) CH2Cl2, CH3Cl, CH4 (B) CH4, CH3Cl, CH2Cl2 (C) CH3Cl, CH2Cl2, CH4 (D) CH3Cl, CH4, CH2Cl Q.46 Fe/HClreduction of‘pyrene’(CCl4)gives: (A) CH4 (B) CH2Cl2 (C) CH3Cl (D) CHCl3 Q.47 Additionofbromine onpropene inthe presence ofbrine yields a mixture of: (A) CH3CHClCH2Br and CH3CHBrCH2Cl (B) CH3CHClCH2Br and CH3CHBrCH2Br (C) CH3CHClCH2Cl and CH3CHBrCH2Br (D) CH2CHClCH2Cl and CH3CHBrCH2Cl Q.48 is converted into by: (A) (i) CH3– MgI, H3O+ (ii) H2SO4, , (iii) HBr, R2O2 (B) (i) CH3– MgI, H3O+ (ii) H2SO4,  , (iii) HBr (C) (i) CH3– MgI, H3O+ (ii) HBr (D) (i) HBr, R2O2 (ii) CH3– MgI, H3O+ Q.49 To formMalonicacid, byshortest possible route, we have to start a reactionfrom: (A)Ethyledine chloride (B) Methylchloride (C) Methylene chloride (D) Chloro ethan Q.50 Frankland reagent is: (A)Dialkyllithium (B)DialkylZinc (C)Dialkylmagnesium (D)Dialkylaluminium
  • 8. EXERCISE–I (B) (Choose the correct option. One or more than one are correct) Q.1 Inthegivenreaction:    2 Br [X] [X]is: (A) (B) (C) (D) Q.2 Consider thefollowing statements? (A) CH3–CH2–CH2–I willreact more readilythan (CH3)2 CHI for SN2reactions. (B) CH3–CH2–CH2–Cl will react more readily than CH3–CH2–CH2–Br for SN2reaction. (C) CH3–CH2–CH2–CH2–Br will react more readilythan (CH3)3C–CH2–Br for SN2 reactions (D) CH3–O–C6H5–Br willreact more readilythan NO2–C6H5–CH2Br for SN2reaction Q.3 Asolutionof(R)-2-iodobutane, [] =–15.9°inacetone istreated withradioactive iodied, until1.0% of iodobutane contain radioactive iodine, the specific rotation of recovered iodobutane is found to be 15.58°, whichstatement is correct about above information. (A) It hasopticalpurity96% (B) % ofR in solutionis 99% (C) Racemicmixture is 2% (D) Finalsolutionis dextrorotatory Q.4 Whichare possibleproducts in following       O Ag moist 2 (A) (B) (C) (D) Q.5 In which product formation takes place accordingto Hoffmann's rule (A) Br | CH CH CH CH 3 2 3           K O u B t  (B) Br | CH CH CH CH 3 2 3           K O CH CH 2 3  (C)      H O  (D) 2 3 3 2 3 ) CH ( S | CH CH CH CH        H O 
  • 9. Q.6 A + B       O H ) ii ( O Et ) i ( 3 2 Alcohol Acetone CrO H 4 2      Ketone Ketone is ifAis grignard reagent, then (A)Aisisobutylmagnesiumbromide (B) B is 3 3 CH | O CH CH CH    (C) B is CHCOCl CH | CH 3 3  (D)Ais isopropylmagnesiumiodide Q.7     hv , Br2 (A) Br CH CH CH | CH 2 3 3   (B) 3 3 3 CH CBr CH | CH   (C) CH3CH2CH2Br (D) 3 3 CH CH CH | Br   Q.8 Select the correct statements fromfollowing (A) CH3CH2CH2I willreact more readilythan (CH3)2CHI for 2 N S (B) CH3CH2CH2Clwillreact more readilythan CH3CH2CH2Br for 2 N S (C) CH3CH2CH2CH2Br willreact more readily than (CH3)2CH–CH2Br for 2 N S (D) CH3–O–C6H4–CH2Br willreact more readily than NO2–C6H4–CH2Br for 2 N S Q.9 Whichofthe following willreact withAcOAg (A) R–NH2 (B) R–OTs (C) R–N3 (D) R–Br
  • 10. Q.10 Consider thegivenreaction ) S ( H C | OTs C H | CH 5 2 3       NaCN 3 2 3 CH | CN CH CH CH  whichoffollowing statements are correct for above reaction. (A) Product formationtakes place due to the breaking ofO–Ts (B) The reaction is 2 N S (C) The reaction is 1 N S (D) Configuration ofproduct is (R) Q.11 Benzoylchloride isless reactive thanacetylchloride for nucleophilic acylsubstitution reactionbecause (A)  C || O group ofbenzoylchloride is inconjugationwithbenzene ring. This makes benzoylchloride more stablethan acylchloride. (B) CH3– group ofacetylchloride make C–Clbond stronger due to the +I effect. (C) C6H5– group of benzoyl chloride make C–Clbond weaker due to +R effect. (D) Carbonylcarbon in benzoylchlorideis less electrondeficient thanacetylchloride Q.12 Brominationcantake place at 4 CCl hv / NBS      (A) 1 (B) 5 (C) 3 (D) 4 Q.13 Whichoffollowingwillgivesyn-elimination (A) CH3CH2CH2–OCOCH3 (B) Cl | CH CH CH CH 3 2 3  (C) S | | CH S C O CH CH CH 3 2 2 3     (D) 3 2 2 3 3 CH | O N CH CH CH | CH   
  • 11. Q.14 Which offollowing are correct for givenreaction    (A) Major product ofreaction is (B) Major product is (C) The reactionis thermaleliminationreaction (D) The reactionis cyclic E2 reaction Q.15 Haloformreactionis givenby (A)All2° alcohol (B)Allmethylketones (C)Allthe compounds having O | | C CH3   group (D) Chloral Q.16 Identifythecompounds that willundergo NGP reaction (A) CH3CH2–S–CH2CH2Br (B) CH3–NHCH2CH2CH2Br (C)  O Br | | O C CH CH3    (D) CH3–O–CH2CH2CH2Br Q.17 Whichalkylhalide undergo E2 elimination (A) (B) (C) (D) Q.18 3-Phenyl-3-pentanolcanbe prepared fromgrignard reagent & other component which can be (A) 3-pentanone (B) Ethylbenzoate (C) Ethylphenylketone (D)Propanoylchloride Q.19 Inwhichoffollowing reactioninvertedproduct willobtained. (A) SN1 (B) SN2 (C) NGP N S (D) SNi Q.20 Rate ofSN2 willbe negligible in (A) (B) (C) (D)
  • 12. Q.21 SN1 & SN2 is not favourable in (A) H2C = CH–Cl (B) Ph–CH2–Cl (C) Ph–Cl (D) H2C=CH–CH2–Cl Q.22 SN1 & SN2 product are same in (excluding stereoisomer) (A) (B) (C) (D) Cl CH | | CH CH CH Ph 3 3    Q.23 Rate of SN2 depends on (A) Conc ofNucleophile (B) Conc ofsubstrate (C) Natureofleaving group (D) Natureofsolvent Q.24 G     NaOI yellow solid G can be (A) O | | OCH C CH 3 3   (B) O O | | | | CH C CH C CH 3 2 3     (C) CD3COH (D) Q.25 Match the List I (reaction) withList II (reaction intermediate)and select the correct answer usingthe codes givenbelow the Lists. List I List II (A) CF3–CHCl2        / KOH . alc CF2 = CCl2 (1) Transitionstate (B) 3 3 3 CH | OH C CH | CH       H 3 2 3 CH | CH C CH   (2) Carbocation (C) CH3–CH2–Br       KOH . alc CH2=CH2 (3) Carbanion (D) 3 3 3 CH | CH C CH | Br          / KOH . aq 3 2 3 CH | CH C CH   (4) Free radical
  • 13. Q.26 Match theList I withList II and select the correct answer usingthe codes givenbelow the Lists. List I List II (A) E1CB (1) QuaterneryAmine oxide (B) Saytzeffalkene as major product (2) Xanthate (C) E2 (3) 3 2 3 CH CH CH CH | Cl    (D)EC (4) F | CH CH CH H C 3 2 5 6    Q.27 MatchList I with List IIand select the correct answer fromthe codes given below: List I List II (A) CH3–O–SO2CH3 +  O H C 5 2 (1) CH3–CH2–PH2 (B) CH3–CH2–I + PH3 (2) CH3–O–C2H5 (C)   Na C HC  + CH3–CH2–Br (3) CH3–O–CH3 (D) CH3–Cl + CH3–  O (4) CHC–CH2–CH3 Q.28 MatchList-I withList-II forgiven 2 N S reaction&select the correct answerfromthe codesgivenbelow Z–CH2Br +  O CH3  Z–CH2–OCH3 +  Br List-I List-II (A) H– (P) 0.1 (B) CH3– (Q) 3 (C) C2H5– (R) 1 (D) (S) 100 Q.29 Match List-I & List-II and select correct answer List-I List-II (A) R–MgX + HCHO Adduct      O H3 (P) Ketone n-carbon (B) R–MgX + (CH2)2O Adduct      O H3 (Q) 1°Alcohol(n + 1) carbon n-carbon (C) R–MgX + CO2 Adduct      O H3 (R)Acid (n+ 1) carbon n-carbon (D) R–MgX + Ph–CN Adduct      O H3 (S) 1°Alcohol(n + 2) carbon
  • 14. Q.30 Matchthe following List-I List-II (A)         O CH CH 2 3 (P) E1 (B) OD CH CH O CH CH 2 3 2 3        (Q) E2 (C) moist O Ag2     (R) E1cb (D)      KOH . alc (S) Ec
  • 15. EXERCISE–II Q.1 Explain the following giving proper resoning : (i) Treatment of1,1-dimethyloxirane withsodiummethoxideinmethanolgives primarilyone product.Also identifythe product giving its IUPAC name (ii) Trimethylamine reacts with alkyl iodide (RI).As the reaction proceeds the reaction rate abnormally increases, inspite ofdepleting concentrationofreactants. (iii) Optically active 2-iodo butane on treatment with NaI*/Acetone gives a product which do not show opticalactivity. (iv) Inthe solvent DMSOthe order ofreactivityofhalide ions withmethylbromide is F— > Cl— > Br— > I— opposite to that observed inmethanolsolution. (a) (n - C3H7)3N + CH3I  (n – C3H7)3NCH3 + I— Relative rate :in hexane, 1 ;in chloroform, 13000 (b) Br— + CH3OTs  CH3Br + TsO— Relative rates : in methanol, 1;in HMPT, 105. (v) Although ethers are weaklypolar, are used as solvent ofchoice for Grignard reagents. (vii) Treatment ofeither CH3– –CH2 Br or CH3– Br | CH – with aqueous HO— gives the same product.Also write downmechanisminvolved, &IUPAC name ofproduct. Q.2 On reaction between an alkyl halide and KOH in a mixture of water and ethanol, compare the two mechanisms SN1 and SN2 : (a) relative rates ofCH3X, C2H5X, iso-C3H7X & tert-C4H9X (b) relative rates for RCl, RBr and RI (c) effect onrate ofa rise in temperature (d) effect onrateofincreasing water content ofthe solvent. (e) effect onrate increasing alcoholcontent ofthe solvent. Q.3 Inthefollowingreactionis carriedout intheweaklyionizingsolvent, acetone (CH3)2C=O. (Bsis brosyl, p-bromo benzene sulfonyl) n-C4H9OBs + X—  n-C4H9X + BsO— The order ofreactivityofhalide ions depends or the salt used on their source : ifLi+X— is used, I— > Br— > Cl— if (n-C4H9)4N+ X— is used Cl— > Br— > I— How do you account for this contrast in behavior ? Q.4 Whichofthe following is thecorrect method for synthesizing4,4-dimethyl-pent-2-yne, using sodamide in liquid NH3? Givenreasons. (i) CH3CCH + 3 3 3 CH | Br C CH | CH    (ii) 3 3 3 CH | CH C C CH | CH    + CH3I  Q.5 Give the products and find allunknowns. (a) H2N CH2 CH2 CH2 CH2 Br  
  • 16. (b) (c) Pyridine TsCl     A A    NaBr B C Q.6 Find out the unknown alphabets. (a) + CH3CH2MgBr (1 eq)      O H3 A A (b)      O H3 B (2 eq) (c) H–C || O –OEt + CH3CH2MgBr      O H3 C (2 eq) (d)      O H3 D (1 eq.) Q.7 To prepare OH | H C C | H C 5 2 5 2    byRMgX which is the incorrect pair (a) MgBr + (C2H5)2CO     O H2 (b) C2H5MgBr +     O H2 (c) C2H5MgBr + –COOCH3     O H2 (d) MgBr + C2H5COOCH3     O H2
  • 17. Q.8 KOH . alc   (A)       K BuO t CHBr – 3 (B) Q.9 3 2 3 CH | Cl CH CH CH CH | Cl     convert ? Q.10 What is/are thelimitation in the formationofGrignard reagent byRX + Mg      ether dry (a) R should not containanyacidic group (b) R should not containanyelectronegative group (c) Alkylhalide shouldnot be vicinaldihalide (d) Alkylhalide can't be Tertiary. Q.11 Identifytheunknowns (a) CH3CH2Cl + I—  A (b) (CH3)2CH–Br + KOH (aq.)  B (c) (CH3)3C–Br + KCN (alc.)  C (d) (CH3)3C–Br + KOH (aq.)  D (e) Q.12 Write majorproduct ofthe thefollowing reactions: (i) ClCH2CH2CH2Br + KCN heat EtOH     A (ii) PhCHO    4 SF B (iii) BrCH2CH = CHCO2Me DMF AgF     C (iv) EtOH + HI  D (v) EtOH + HCN  E Q.13 State at least one characteristic test whichcandistinguish: (i) C2H5OH from CHCl3 (ii) Halogen atoms present in CHCl3 and CH2 = CHCl (iii) 1, 1- dibromoethane from1, 2-Dibromethane (iv) Chlorobenzene fromchlorocyclohexane (v) o-Chlorotoluene frombenzylchloride (vi) n-Hexane, CH3CH = CHCl, CH2= CHCH2Cl and CH3CH2CH2Cl Q.14 CH3–CH2I reacts more rapidly with strong base incomparison to CD3CH2I Q.15 2-chloro-3-methylbutane ontreatment withalcohoilc potashgives 2-methylbutene-2as major product. Q.16 Iodoformgives precipitate withAgNO3 onheating while CHCl3 does not.
  • 18. Q.17 Hydrogen atomofchloroformis definatelyacidic, but that ofmethane is not. Q.18 Asmallamount ofalcoholis addedto chloroformbottles. Q.19 Treatment of Me3CCH = CH2 and Me3CCHOHMe with concentrated hydrochloric acid gives the same two isomeric alkylchlorides what are these two products. Q.20 Iodine reactswith alcohols to give alkyliodine onlyinpresence ofphosphorous. Q.21 KCN reacts with R – I to give alkylcyanide, whileAgCN results in isocyanide as major product. Q.22 The carbocation F3C –  C < is unstable whereas carbocation F3C+ is more stable. Q.23 Drygaseous hydro halogen acid and not their aqueous solutions are used to preparealkylhalides from alkenes. Q.24 RClis hydrolysed to ROH slowlybut reaction fastens onaddition ofKI. Q.25 The mechanism ofdecomposition ofMe3 S+ OH– is SN2 whereas of Me3S+ I– is SN1. Q.26 Alkalinehydrolysisofbenzylchloridein50%aqueousacetoneproceedsbybothSN2andSN1mechanism, when water is used as solvent, mechanismwas now mainlySN1. Q.27 Ethanolis less reactive than methanolas wellas isopropylalcohols whentreated withdryHClgas. Q.28 AnhydrousAlCl3 is usedas a catalyst infriedelcrafts alkylation. Q.29 Arrange following compoundsaccording to their reactivitywithalc silver nitrate. t-Butylchloride, sec butylchloride and CCl4. Q.30 (a) (b) What are (A) and (B) explaingiving their stereochemistry. Q.31 n-C10H21Br + HC CNa  A       Li Bu n B 5-methyl-1-hexene + HBr (peroxides)  C  B D        . cat s ' lindlar / H2 E         acid benzoic peroxy F
  • 19. Q.32 Complete the followingbyproviding (A), (B), (C) and (D): (i) CH3CH2CH2OH     3 PBr (A)      KOH . Alc (B)     HBr (C)     3 NH (D) (ii) CH3CH2CH2I      KOH . Alc (A)       O H / H 2 (B)     2 SOCl (C) 4 LiAlH H   (D) (iii) CH3CH2CH = CH2 Light NBS     (A)      KOH . Alc (B)     HBr (C) (iv) CH3CH2MgBr        O H / CHO CH 2 3 (A)     HBr (B)      KOH . Alc (C) Q.33 Carryout following conversions. (a) 3 3 CH CH CH | Cl   — CH3–CH2–CH2–Cl without using peroxide (b) CH3–CH2–CH2–Cl — Cl | CH CH CH 3 3   insingle step (c) — in three steps only (d) — in three steps only (e) Cl C CH Ph || O 2    — Ph – CH2 – Cl (f) Ph – CH2 – Cl — Cl C CH Ph || O 2   
  • 20. EXERCISE–III Q.1 Aprimaryalkylhalide (X) C4H4Br reacted withalcoholic KOH to give(Y). (Y) reacts withHBr to give (Z) anisomer of(X). Onreacting withalkalimetalsuchas sodium/dryether gives (S) C8H18 whichwas different fromthe compound produced when n-butylbromidewas treated with Na. What (X), (Y), (Z) and (S). Q.2 On electrolysis anaqueous ethanoilc solution ofsodiumchloride gives sweet smelling liquid (X). (X) gives isocyanide test and condenses withacetone to fromhypnotic(Y). What are (X) and (Y)? Q.3 The alkyl halide C4H9Br (A) reacts with alcoholic KOH and gives an alkene (B), which reacts with bromide to give dibromide (C). (C) is transformed with KOH & sodamide to gas (D) which forms a precipitate whenpassedthroughanammonicalsilvernitrate solution. Give thestructureformulae ofthe compounds (A), (B), (C) and (D) and explain reactions involved. Q.4 An unsaturated hydrocarbon (A) C6H10 readily gives (B) on treatment with NaNH2 in liquid NH3. When(B)isallowedto reactwith1-chloropropane,acompound(C)isobtained. Onpartialhydrogenation inthe presence ofLindlarcatalyst, (C) gives (D), C9H18. Onozonolysis (D) gives2, 2-dimethylpropanal and 1-butanal. Give structures of(A), (B), (C) and (D) withproper reasoning. Q.5 One mole of each bromoderivative (A) and NH3 react to give one mole ofan organic compound (B). (B) reacts with CH3I to give (C). Both (B) and (C) react with HNO2 to give compounds (D) and (E), respectively. (D) onoxidation and subsequent decarboxylation gives 2 -methoxy-2-methylpropane. Give structuresof(A) to (E) with proper reasoning. Q.6 A chloro derivative (A) on treatment with zinc-copper couple gives a hydrcarbon with five carbon atoms. When'A'is dissolved in eitherand treated with sodium, 2,2,5,5-tetramethylhexane is obtained. What is theoriginalcompound 'A'? Q.7 Aprimaryalkylhalide (A) C4H9Br reacted withalcoholic KOH to give(B). (B) reacts withHBr to give (C) an isomers of (A). (A) on reacting with sodium gives (D) C8H18 which was different from the compound produced whenn-butylbromide was treated withNa.What are (A), (B), (C) and (D). Q.8 One mole ofa hydrocarbon (A)reacts with1 mole ofbromine giving a dibromo compound C5H10Br2. (A) ontreatment withcold dilute alkaline KMnO4 solutionformsa compound C5H12O2. on ozonolysis (A) givesedquimolar quantities ofpropanone and ethanal. Deduce structure of(A). Q.9 A hydrocarbon (A) was found to contain 85.7% carbon and 14.3% H. This compound consumes 1 molar equivalent ofhydrogento give asaturated hydrocarbon. 1g of(A) just decolourised38.05of5 % solution byweight ofBr2 in CCl4. Compound (A) on oxidation withconc. KMnO4 gave a compound (C), C4H8O and(B) acetic acid. Compound (C) caneasilybe prepared bythe actionofacidic aqueous mercuric sulphate on 2-butyne. Deduce (A), (B) and (C). Q.10 When a hydrocarbon (A) is treated with excess of hydrogen chloride, a dihalogen derivative (B) is obtained. The compound(B) is treated separatelywithaqueous and alcoholic KOHto give compounds (C) and (A) respectively both having three carbon atoms. Compound (C) does not reduce Tollen's reagent and compound (A) give white precipitate with ammonical silver nitrate.Assign structures to compounds (A) to (C).
  • 21. Q.11 An organic compound (A) C7H15Clontreatment withalcoholiccaustic potashgives ahydrocarbon(B) C7H14. (B) ontreatment withozone andsubsequent hydrolysis gives acetoneand butyraldehyde. What are (A) and(B). Explain reactions. Q.12 A dihalogenderivative (A) ofa hydrocarbon having two carbonatoms react with alcoholicpotashand forms anotherhydrocarbon whichgives ared precipitate withammonicalcuprous chloride. Compound (A) gives an aldehyde when treated with KOH (aq). What is (A)? Q.13 Awhite precipitate was formed slowly whenAgNO3 was added to a compound (A) with molecular formula C6H13Cl. Compound (A)ontreatment withhot alcoholic KOH gave a mixtureoftwo isomeric alkenes (B) and (C) having formula C6H12. The mixture of(B) and (C) onozonolysis furnished four compounds (i) CH3CHO, (ii) C2H5CHO, (iii) CH3COCH3, (iv) (CH3)2CH.CHO What are (A), (B) and (C). Q.14 0.369 g ofa bromo derivative ofa hydrocarbon(A) when vaporizedoccupied 67.2 mLat NTP. (A) on reactionwithaqueousNaOHgives(B).(B)whenpassedoveraluminaat 250°Cgivesaneutralcompound (C) whileat 350°C it givesa hydrocarbon(D). (D)whenheated withHBrgives anisomer of(A). When (D) is treated with dil. H2SO4 , (E) is obtained. Identify(A) to (E) and explain the reactions. Q.15 An organic compound (X) on analysis gives 24.24 % C, 4.04% H. Further sodiumextract of1.0 g of (X) gives 2.90 g ofAgClwith acidifiedAgNO3 solution. The compound (X) maybe represent bytwo isomericstructures(Y)and(Z).(Y)ontreatmentwithaqueousKOHsolutiongivesadihydroxycompound, while (Z)on similar treatment givesethanal. Find out (X), (Y) and (Z). Q.16 Achloro compound (A) showed thefollowing properties : (i) Decolourized bromine inCCl4 (ii) Absorbed hydrogencatalytically. (iii) Gave a precipitate withammonicalcuprous chloride (iv) When vaporised 1.49 g of (A) gave 448 mLofvapours at STP. Identify(A)and write downtheequations ofreactions.
  • 22. EXERCISE–IV (A) Q.1 Chlorinationoftolueneinthe presenceoflight and heatfollowedbytreatment withaqueousNaOH gives (A) o-cresol (B) p-cresol (C) 2,4-dihydroxytoluene (D) Benzoic acid Q.2 Aryl halidesarelessreactivetowardsnucleophilicsubstitutionreactionascompared to alkyl halidesdueto (A) Theformation of lessstablecarbonium ion (B) Resonancestabilization (C) Theinductiveeffect (D) sp2 hybridised carbonattached to the halogen Q.3 1-Chlorobutane on reactionwithalcoholic potash gives: (A) 1-butene (B) 1-butanol (C) 2-butene (D) 2-butanol Q.4 The products ofreaction ofalcoholicAgNO2 withethylbromide are (A)Ethane (B)Ethylnitrite (C) Nitroethane (D) Ethylalcohol Q.5 When nitrobenzene is treated with Br2 in presence ofFeBr3 the major product formed is: m-bromonitrobenzene. Statementswhich are related obtainthe m-isomer are (A) The electrondensityon meta carbonis more than on ortho and para position (B) The intermediate carbonium ion formed after initial attack of Br+ at the meta position is least destabilized. (C) Loss ofaromaticitywhen Br+ attacks at the ortho and para position and not at meta position (D) Easier loss ofH+ to regain aromaticityfromthe meta positionthanfromotho andpara positions. Q.6 Arrange the followingcompounds inorder ofincreasing dipole moment Toluene m-dichlorobenzene o-dichlorobenzene p-dichlorobenzene I II III IV (A) I < IV < II < III (B) IV < I < II < III (C) IV < I < III < II (D) IV < II < I < III Q.7 In the reaction ofp-chloro toluene with KNH2 in liq. NH3, the majorproduct is: (A)o-toluidine (B)m-toluidine (C) p-toluidine (D)p-chloraniline Q.8 (CH3)3CMgClreaction with D2O produces: (A) (CH3)3CD (B) (CH3)3OD (C) (CD3)3CD (D) (CH3)3OD Q.9 Benzylchloride (C6H5CH2Cl) canbe prepared fromtoluenebychlorination with: (A) SO2Cl2 (B) SOCl2 (C) Cl2 (D) NaOCl Q.10 Toluene, when treated with Br2/ Fe, gives p-bromotoluene as the major product, because the CH3 group (A) is para directing (B) ismeta directing (C) activates the ring byhyperconjugation (D) deactivatesthe ring Q.11 The order ofreactivityofthe following alkylhalidesfor a SN2reaction is: (A) RF > RC > R–Br > R–I (B) R–F > R–Br > R–Cl > R–I (C) R–Cl > R–Br > RF > RI (D) R–I > RBr > R–Cl > R–F
  • 23. Q.12 Identifytheset ofreagents /reaction conditions 'X'and'Y' in the followingset oftransformation: CH3 – CH2 – CH2Br   X Product   Y Br | CH CH CH 3 3   (A) X = dilute aqueous NaOH, 20°C;Y = HBr / acetic acid, 20°C (B) X = concentrated alcoholic NaOH, 80°C;Y = HBr/ acetic acid 20°C (C) X = dilute aqueous NaOH, 20°C; Y = Br2 / CHCl3, 0°C (D) X = concentrated alcoholic NaOH, 80°C;Y = Br2/CHCl3, 0°C Q.13 CH3MgBr + Ethylester  whichcan be formed as product. (excess) (A) (B) (C) (D) Q.14 Matchthefollowing: ColumnI ColumnII (A) CH3–CHBr–CD3 on treatment with alc. KOH gives (P) E1 reaction CH2=CH-CD3 as a major product. (B) Ph – CHBr - CH3 reacts faster than Ph-CHBr-CD3. (Q) E2 reaction (C) Ph-CH2-CH2Br on treatment with C2H5OD/C2H5O– (R) E1cb reaction gives Ph-CD=CH2 as the major product. (D) PhCH2CH2Br and PhCD2CH2Br react with same rate. (S) First order reaction EXERCISE–IV (B) Q.1 Fillinthe blanks: (a) Butan nitrile canbe prepared byheating _____with alcohalic KCN. (b) Amongst three isomersofnitrophenol, the onethat is least soluble in water is_____ Q.2 Identifythemajor product inthefollowing reactions : (i) 3 2 5 6 CH CH CH H C | Cl          KOH alcoholic ?   HBr ? (ii) C6H5COOH + CH3MgI  ? + ? Q.3 AnalkylhalideX offormula C6H13Clontreatment withpotassiumtertiarybutoxidegives two isomeric alkenesYandZ (C6H12). Bothalkenesonhydrogenationgive2,3–dimethylbutane. Predict the structures ofX, Yand Z.
  • 24. Q.4 Predict the structure ofthe intermediates/productsin the following reactionsequence – Acetone NaI    C Q.5 (a) CHCl CH H C | H C 2 5 6 5 6 Heat KOH Alcohalic        A+ BWrite structures of(A) and (B). (b) (CH3)2CHOCH3 Heat ) excess ( HI       A+ B Write structures ofAand B. Q.6 Complete thefollowing reaction withappropriatestructures ofproducts/reagents.    2 Br (A) I CH ) II ( .) equi 3 ( NaNH ) i ( 3 2         (B) Q.7 What would be major product? 3 2 3 3 CH | Br CH C CH | CH   e temperatur low at OH H C      5 2 ? Q.8 How would you synthesis 4 methoxyphenolfrombromobenzene in NOT more thanfive steps? State clearlythe reagents used in eachstep and show the structures ofthe intermediate compounds in your synthetic scheme. Q.9 An alkeneA(C16H16) onozonolysis give onlyoneproduct B (C8H8O). Compound B onreaction with NaOH/I2 yields sodiumbenzoate. Compound B reacts with KOH/NH2NH2 yielding a hydrocarbon C (C8H10). Write the structure ofcompound B and C. Based on this information two isomeric structures can be prepared for alkene A. Write their structures and identify the isomer which on catalytic hydrogenation (H2/Pd–C) gives a racemic mixture. Q.10 Give major productsA, B, C and D in following reaction sequence. DMF KCN     (A)         / PhCHO ) ii ( EtOH / NaOEt ) i ( (B)      O H3 (C) (D)
  • 25. ANSWER KEY EXERCISE–I (A) Q.1 D Q.2 A Q.3 C Q.4 D Q.5 A Q.6 D Q.7 A Q.8 B Q.9 C Q.10 C Q.11 C Q.12 C Q.13 A Q.14 D Q.15 C Q.16 B Q.17 A Q.18 D Q.19 C Q.20 D Q.21 B Q.22 C Q.23 D Q.24 C Q.25 D Q.26 B Q.27 B Q.28 A Q.29 B Q.30 C Q.31 B Q.32 B Q.33 C Q.34 C Q.35 A Q.36 A Q.37 C Q.38 C Q.39 A Q.40 B Q.41 A Q.42 A Q.43 A Q.44 B Q.45 A Q.46 D Q.47 B Q.48 A Q.49 C Q.50 B EXERCISE–I (B) Q.1 D Q.2 A,C Q.3 B,C Q.4 A,B Q.5 A,C,D Q.6 A,B,C Q.7 B Q.8 A,B,D Q.9 B,C,D Q.10 B,D Q.11 A,D Q.12 A,C,D Q.13 A,C,D Q.14 A,C,D Q.15 B,D Q.16 A,B,C,D Q.17 A,B Q.18 A,B,C Q.19 A,B Q.20 A,B,C Q.21 A,C Q.22 B,C Q.23 A,B,C,D Q.24 B,C,D Q.25 A  3, B  ,C  1,D  2 Q.26 A  4, B  3,4, C  3, D  1,2 Q.27 A  2, B  1, C  4, D  3 Q.28 (A) – S; (B) – Q; (C) – R; (D) – P Q.29 (A) – Q; (B) – S ; (C) – R; (D) – P Q.30 (A) – Q; (B) – R ; (C) – P; (D) – Q EXERCISE–II Q.1 (i) OH | CH CH CH | | CH O CH 2 3 3 3    attack take place on less stericallycarbon Q.4 (ii) Q.5 (a) (c) (A) Me CH C Me | Me    , (B) OEt | Me CH C Me | Me 2    , (C) I | Me CH C Me | Me 2   (d) (A) , (B) , (C)
  • 26. Q.6 (a) (b) (c) Et CH Et | OH   (d) Q.7 (d) Q.8 A  B  Q.9 A  3 2 3 CH | CH CH CH CH    B  C | Cl C C C C     Conversion (1) NaNH2 (2) H2/Pd BaSO4 Q.10 (a) & (c) Q.11 (a) A Et – I (b) B  OH CH CH | CH 3 3   (c) Me2C=CH2 (d) Me2C=CH2 (e) & OH | CH OH Me | OH 2   Q.12 The mechanismof (i) ClCH2CH2CH2CN (ii) PhCHF2 (iii) FCH2CH = CHCO2Me (iv) EtI (v) no reaction Q.13 (i)Chloroformrespondscarbylamine test while ethylalcoholdoes not. Carbylaminetest-Thecompound is heated withaniline and alcoholic causticpotash-an obnoxious smellofphenylisocyanide (C6H5NC) is produced. (ii) Chlorine atoms ofchloroformcanbeeasilyreplaced by– OH groups on treatment with NaOH. Hence chlorine atomscome inthe formofsodiumchloride. The solution thus whentreatedwithsilver nitrate solutiongiveswhite precipitate ofsilverchloride. Chlorine atominvinylchloride is not readilyreplaced byNaOH, hence it does not give precipiatet withAgNO3 solution. (iii) The two compounds are hydrolysed withaqueous NaOH when1, 1-dibromoethane formacetaldehyde while 1, 2-dibromoethane gives glycol. (iv) Chlorineatominchlorobenzene is verylessreactive, whilechlorineincyclohexylchlorideisveryreactive. Hence the two can be differentiated as above in (ii) (v) Apply test (ii) as above; when benzylchloride gives white precipitate withAgNO3 solution, while O chlorotoluene doesnot give precipitate.Alternately, the compounds are oxidisedwheno chlorotoluene give o-chlorobenzoicacid whenbenzylchloride gives benzoic acid (havingnon chlorine.) (vi) n - Hexane does not respond Cl– iontest even after fusionwith Na and treatment with acidicAgNO3. the remaining three compounds are distinguished bytheir reactivitywithalcoholicAgNO3 solution. (a) CH3 – CH = CHCl (a vinylic chloride) does not react with alc.AgNO3 evenon heating (b) CH2 = CHCH2Cl(an allylic chloride) is the most reactive and precipitatesAgClin the cold. (c) CH3–CH2–CH2–Clgives precipitate ofAgClon warming withAlc.AgNO3
  • 27. Q.14 TheeliminationofHI (orDI) inpresence ofstrongbaseshows E2elimination. Therate determiningstep involves breaking up of C – H (or C–D) bond. the C–D bond being stronger than C–H and thus elimination is faster in case ofCH3 – CH2I. Q.15 Cl CH | | CH CH CH C H 3 3 3         ) alc ( KOH or min major CH CH | | CH CH CH CH CH CH C CH 3 3 2 3 3 3        Elininationoccursaccording to saytzeffrule. The major product isone which involves eliminationofH fromless hydrogenated carbon. Q.16 C–I bond being less stable than C–Cl bond and thus on heating heterolytic cleavage of C –I form I– whichgives yellowprecipitate withAgNO3 Q.17 Due to three electronegative chlorine atoms present on carbon, the latter acquires a partial positive charge due to –I effect ofchlorine with the result it tends to attract electrons ofthe C–H bond towards itself. Hence the removalofhydrogen atomas proton becomes easier. Q.18 Alcoholacts asnegative catalyst for oxidationofchloroform.Also it reacts withCOCl2 to giveharmless diethylcarbonate. Q.19 Carboniumions canundergo rearrangement fromlessstable to more stable ones. Bothcompounds give the same carboniumioninitially. Hence Me3CCHOHMe O H ) ii ( H ) i ( 2       HMe C C Me | Me 2        H Me3CCH = CH2Cl– rearrangement Me3CCHClMe Me2 2 CHMe C      Cl Me2CClCHMe2 Bothgivethesametwoisomericchlorideinthesameproportions, withthetertiarychloridepredominating. Q.20 Phosphorus reacts with I2 to give PI3 whichreplaces OH group ofalcoholto produce R – I 2P + 3I2  2 PI3 3R OH + PI3  3RI + H3PO3 Q.21 KCN is an ionic compound [K+(:C N:)–] in which both C and N carry a lone pair electron. Carbon carrying lone pairofelectrons is morereactive and thus alkylattacks carbonto givealkylcyanideAgCN being covalent hasAg– CN : structure with lone pair on N thus R attacks N atom and R–N   C is formed. Q.22 The strong – I.E offluorine atom in F3C –  C < produces partial +ve charge on C atom ofCF3 which ultimatelyincreases + ve charge on2nd carbonatomto destabilize it
  • 28. F C F F          In F3C+, the unsharedpair ofelectrons in the p orbitals ofeachofthe fluorine atomareshifted to C+ via p–p orbitaloverlapping and thus stablizing F3C+ ion Q.23 Drygaseoushydro halogenacidsarebetterelectrophile.Also inaqueoussolutionH2Oactingasnucleophile mayproduce alcohol. Q.24 KI reacts with RCl to form RI. This RI molecule now hydrolysed easily to give ROH because alkyl iodide are more reactive than alkylchloride. RCl + KI  RI     HOH ROH (more fast) Q.25 Themorepronouncedthenucleophilicactivityoftheattackingreagent,thenthemoretheSN2mechasnism will be favoured. Since in SN1 mechanismthe raegent doesnot enter into the rate determining step of ionisationHoweverit canalso beexpected that asthenucleophilicactivtiyisso slowthat themechanism willchange fromSN2 to SN1 Q.26 The dielectric constant of water is greater than that ofaqueous acetone, and so ionisation of benzyl chloride isfacilitated. Q.27 Onmoving from3°to 1°alcoholrateofSN2reactiondecreasesand reaches to minimumand mechanesm changes fromSN2 to SN1, Thenrate ofSN1 rate ofreaction increases. Q.28 AnhydrousAlCl3 is usedas a catalyst infriedelcrafts alkylation. Q.29 tert-Butylchloride, sec butylchloride and CCl4 withalc. silver nitrate Me3C – Cl > CHCl > CCl4 Q.30 (a) A B  C  D  E  F  G  H  I 
  • 29. (b) (A) , (B) Q.31 A  C10H21–CCH B  CLi C H C 21 10     C  C | Br C C C C C C       D  3 3 4 2 21 10 CH | CH CH ) CH ( C C H C      E  3 3 4 2 21 10 CH H H | | | CH CH ) CH ( C C H C      F  H O H / / CH CH ) CH ( C C H C | CH 3 4 2 21 10 3      Q.32 (i)A, CH3CH2CH2Br ; B, CH3CH = CH2 ; C, CH3CHBrCH3; D, CH3CHNH2CH3 (ii) A, CH3CH = CH2; B, CH3CHOHCH3; C, CH3CHClCH3; D, CH3CH2CH2 (iii) A, CH3CHBrCH = CH2; B, CH2=CH–CH=CH2; C, CH3CHBrCH=CH2& CH3CH = CH–CH2Br (iv) A, CH3CH2CHOHCH3; B, CH3CH2CHBrCH3; C, CH3CH = CH – CH3 EXERCISE–III Q.1 ) X ( CH | Cl CH CH CH 3 2 3    ) Y ( CH | CH C CH 3 2 3   ) X of isomer ( ) Z ( propane methyl 2 Bromo 2 CH | CH C CH | Br 3 3 3      (CH3)2CH – CH2–CH2–CH (CH3)2 (2,5 –dimethylHexane) (S) Q.2 (Y) Q.3 CH3CH2CH2CH2Br CH3CH2CH = CH2 Br Br | | CH CH CH CH 2 2 3    (A) (B) (C) CH3– CH2– C  CH (D)
  • 30. Q.4 (CH3)3C – C  CH (CH3)3C – C C–Na+ (CH3)3C – C  CH2CH2CH3 (A) (B) (C) (CH3)3C – CH = CHCH2CH2CH3 (D) Q.5 Br CH CH ) CH ( C CH | OCH 2 2 3 3 3     2 2 2 3 3 3 NH CH CH ) CH ( C CH | OCH    (A) (B) 3 2 2 3 3 3 NHCH CH CH ) CH ( C CH | OCH    OH CH CH ) CH ( C CH | OCH 2 2 3 3 3    (C) (D) 3 2 2 3 3 CH | O N N CH CH CH CH | OCH       (E) Q.6 (CH3)3C – CH2Cl Q.7 Br CH CH CH | CH 2 3 3   CH C CH | CH 3 3   Br | CH C C H | CH 3 3 3   (A) (B) (C) 3 2 2 3 3 3 CH CH CH CH CH CH | | CH CH     (D) Q.8 Q.9 C = CH – CH3 CH3–COOH C = O (A) (B) (C)
  • 31. Q.10 CH3– C  CH Cl | CH C CH | Cl 3 3   3 3 CH C CH | | O   (A) (B) (C) Q.11 3 3 2 3 3 CH | Cl C ) CH ( CH | CH   CH3(CH2)2CH = C (CH3)3 (A) (B) Q.12 H3C – CHX2 ( X = Halogen) Q.13 Br | CH CHCH CH ) CH ( 3 2 2 3  (CH3 )2 CH CH = CH CH3 C = C (A) (B) (C) Q.14 (A) CH3CH2CH2Br , (B) CH3CH2CH2OH, (C) CH3CH2CH2OCH2CH2CH3, (D) CH3–CH=CH2, (E) CH3CH(OH)CH3 Q.15 (X) C2H4Cl2, (Y) Cl – CH2CH2 – Cl, (Z) CH3CH Q.16 HC C–CH2– Cl EXERCISE–IV (A) Q.1 D Q.2 D Q.3 A Q.4 C Q.5 A,B Q.6 B Q.7 B Q.8 A Q.9 A,C Q.10 A,C Q.11 D Q.12 B Q.13 D Q.14 A – Q; B – Q; C – R,S; D – P,S EXERCISE–IV (B) Q.1 (a) propylchloride, (b) ortho Q.2 (i) 3 5 6 CH CH CH H C    ; 3 2 5 6 CH CH CH H C | Br    (ii) C6H5COOMgI + CH4
  • 32. Q.3 (X): Cl | CH CH — C CH | | CH CH 3 3 3 3   ; (Y) : 3 2 3 3 CH CH — C CH | | CH CH   ; (Z) : 3 3 3 3 CH CH | | CH CH — C CH   Q.4 (NGP due to MeO, so retentionofconfiguration) Q.5 (a) Cis and trans forms of stibene C6H5CH=CHC6H5 ; (b) Q.6 (A)       .) liq ( NaNH2     I CH3 (B) Q.7 5 2 3 2 3 3 H OC | CH CH C CH | CH   Q.8 pressure high NaOH        4 2SO Me         4 2SO H . conc     NaOH      O H3 Alternativerout       4 2SO H . conc     NaOH 4 2SO Me   pressure high NaOH             O H3 Q.9 (A) PhC(Me)=C(Me)Ph         O H Zn O 2 3 (B) Me PhC 2 | | O  3 3 NH NH KOH      (C) PhCH2Me Two isomers ofAare cis and trans Q.10 (A) ; (B) ; (C) ; (D)