1. ORGANIC CHEMISTRY
C O N T E N T S
EXERCISE - I
EXERCISE - II
EXERCISE-III
EXERCISE IV
ANSWER KEY

2. EXERCISE–I
(Choose the correct option. Only one is correct)
Q.1 Which carbocationis least likelyto formas intermediate?
(A)

C
)
H
C
( 5
5
6 (B) (C) (D) H
C
CH2


Q.2 2-chloropentane onhalogenationwithchlorine gives2,3, dichloropentane. What willbethe structureof
free radicalspecies forminthe reaction?
(A) Planar (B)Trigonalplanar (C) Square planar (D) Pyramidal
Q.3 What willbe major product, when2-methylbutane undergoes bromination inpresence oflight?
(A) 1-bromo-2-methylbutane (B) 2-bromo-2-methylbutane
(C) 2-bromo-3-methylbutane (D) 1-bromo-3-methylbutane
Q.4 The smallest compound, which onphotochlorinationproduces diastereomers is
(A) 3-methyl, 3-chloro hexane (B) 2-chloro butane
(C) 1-bromo propane (D) 1-bromo-3-methylbutane
Q.5 
 

I
CH3




 

O
H
,
O
Ag 2
2
H
The structure of'H' is
(A) (B) (C) (D)
Q.6 
 


OEt
The major product is
(A) (B) (C) (D)
Q.7


 

O
H
RMgX
3
?
(A) (B) (C) (D) None ofthese
Q.8
Br
|
CH
CH
CH
CH 3
2
3 

 

 

KOH
.
alc
(X) (Major)




3
3
2
3
NMe
|
CH
CH
CH
CH


 
EtONa
(Y) (Major)

3. Product (X) &(Y) respectivelyis
(A) 1-butene, trans-2-butene (B) 1-butene, cis-2-butene
(C) cis-2-butene, 1-butene (D) trans-2-butene, 1-butene
Q.9
ether
Mg
equivalent
1




 
 X 
 

O
D2 Y; Y is
is
(A) (B) (C) (D) noneofthese
Q.10 How manynumber ofopticallyactive isomers are possible for 2,3-dibromo butane 1,4-dioic acid?
(A) 2 (B) 3 (C) 4 (D) 1
Q.11 and
Are whichtype ofisomers
(A) Chain (B) Position (C) Metamerism (D)functional
Q.12 Most stable conformationofethylene glycol
(A) Eclipsed form (B) Staggered form (C) Gauche form (D) None ofthese
Q.13
4
2SO
H
)
ii
(
NaCN
)
i
(


 
 Products
Products ofabove reaction are
(A) Racemic mixture
(B) Diastereomer
(C) Meso
(D) Mixture ofmeso compound &opticallyactive compound.
Q.14 Inwhichofthe followingmoleculealltheeffect namelyinductive, mesomeric&hyperconjugationoperate
(A) (B) (C) (D)
Q.15 For the reactions
(I)  + Cl–, o
1
H
 (II)  + Cl– , o
2
H

(III)  + Cl–, o
3
H
 (IV)  + Cl , o
4
H

The correct decreasing order ofenthalpies ofreactionfor producing carbocation is
(A) o
1
H
 > o
2
H
 > o
3
H
 > o
4
H
 (B) o
4
H
 > o
1
H
 > o
2
H
 > o
3
H

(C) o
3
H
 > o
2
H
 > o
1
H
 > o
4
H
 (D) o
2
H
 > o
1
H
 > o
4
H
 > o
3
H


4. Q.16 Correct order ofbasicityofvarious nitrogeninLSD is
(A) 1>2>3 (B) 2>1>3 (C) 2>3>1 (D) 3>2>1
Q.17 One ofthe configurationofn-butane is drawnin the given figure.Anticlockwise rotation ofC2 around
C2–C3 bond by 120° will lead to
(A) gauche (B) staggerred (C) partiallyeclipsed (D) fullyeclipsed
Q.18 Arrange decreasingorder ofreactivityofthese compounds for nucleophilicsubstitutionreaction
(I)
O
|
|
CF
S
O
CH
CH
|
|
O
3
2
3



 (II) CH3–CH2–O–Ts
(III)
OH
|
CH
CH
CH 3
3 
 (IV)
5
6
3
H
C
|
OH
CH
CH 

(A) III, IV, I, II (B) III, IV, II, I (C) I, II, III, IV (D) I, II, IV, III
Q.19 Among the followingpairs in which case the second compound has higher heat ofhydrogenation.
(A) , (B) Cis-2-butene, trans-2-butene
(C) , (D) 1-butene, 2-butene
Q.20
Correct order ofbasicityis
(A) 3>1>2>4 (B) 3<1<2<4 (C) 3<4<1<2 (D) 3>4>1>2
Q.21 The resonance energyoffollowing heterocycles isinthe order
(A) pyrole > furan > pyridine (B) furan > pyrole > pyridine
(C) pyridine > pyrole > furan (D) pyridine >furan > pyrole
Q.22 HBr reactsfastest with
(A) 2-methylbutane-2-ol (B) 3-methylbutane-2-ol
(C) Butane-1-ol (D) 2-methylbutane-1-ol

5. Q.23 Whichofthefollowing alcoholshows fastest reactionwithHI ?
(A) (B) (C) (D)
Q.24 + OH 
 

2
SN
A, A is
(A) (B) (C) Bothare correct (D) None is correct
Q.25 Arrange the following inorder ofC–Br bond strength inpolar solvent.
(I) (II) (III) (IV)
(A) I < II < III < IV (B) III < IV < I < II (C) IV < III < II < I (D) II < I < III < IV
Q.26 
 

EtOH Rate R1

 

EtOH Rate R2

 

EtOH Rate R3
Whichoffollowingis correct :
(A) R1 > R2 > R3 (B) R3 > R2 > R1 (C) R2 > R1 > R3 (D) R2 > R3 > R1
Q.27 (I) , which is not correct about (I)
(A) I ismore soluble than bromocyclopropane
(B) I gives pale yellow ppt. onaddition withAgNO3
(C) I is having lower dipole moment thanbromocyclo propane
(D) I have more ionic character than
Q.28 Whichofthefollowingstatement about the reactivityof1-chloro apocamphane
towardAgNO3 is true.
(A) React bySN1 mechanism (B) React bySN2 mechanism
(C) React bySNimechanism (D) Does not react
Q.29 Arrange the following halideindecreasing order ofSN1reactivity.
(I) CH3CH2CH2Cl (II)
Cl
|
CH
CH
CH
CH 3
2  (III)
Cl
|
CH
CH
CH
CH 3
2
3
(A) I > II > III (B) II > I > III (C) II > III > I (D) III > II > I

6. Q.30




H
(A) (B) (C) (D)
Q.31 


H P. The product P is:
(A) (B) (C) (D)
Q.32 Among the given compounds, the correct dehydration order is:
(I) (II) (III) (IV)
(A) I < II < III < IV (B) II < III < IV < I (C) I < III < IV < II (D) I < II < III = IV
Q.33 IdentifyZinthe following seriesofreaction:
C
170
SO
H
.
conc 4
2




 
 X
4
2
CCl
Br


 Y



 
 KOH
.
alc
Z
(A) (B) (C) (D)
Q.34 In thereaction sequence
3
2
5
6 CH
C
CH
CH
H
C
|
|
|
O
OH








 

)
iii
(
H
/
O
H
)
ii
(
NaOBr
)
i
(
2
product
product willbe
(A) COOH
CH
CH
H
C
|
OH
2
5
6 

 (B) C6H5–COOH, COOH–COOH and CHBr3
(C) 3
5
6 CH
C
H
C
|
|
O

 , CO2 and CHBr3 (D) OnlyCHBr3

7. Q.35 

 


OEt
.
eq
1 A(major product),Ais
(A) (B) (C) (D)
Q.36 


H major product is
(A) (B) (C) (D)
Q.37 

 
NaOBr Product
The product is
(A) (B) (C) (D)
Q.38 
 


O
H3 A, Ais
(A) (B) (C) (D)
Q.39 Which one ofthe following alcoholwillundergo acid catalysed dehydration with greatest ease byE1
mechanism?
(A) CH2 = CH–OH (B) (C) (D) Me2CHOH
Q.40 (A) C3H6O
4
2SO
H
NaCN

 
 cyanohydrin of (A). If the cyanohydrin is optically active, then the possible
structure of(A) is
(A) (B) (C) (D)

8. Q.41 Whichofthe following has minimumreactivitytowards nucleophiles?
(A) CH2O (B) CH3CHO (C) 3
3 CH
C
CH
|
|
O

 (D) 3
2
3 CH
CH
C
CH
|
|
O



Q.42 

 


H
/
ROH
P (major org. product)
The product P is
(A) (B) (C) (D)
Q.43
)
I
(
CH
CH
C
Cl 2
3
1
2
3


In additionofHOBr to (I) and (II)
(A) Br is at C2 in both cases (B) Br is at C2 in II and at C1 in I
(C) Br is at C1 in II and C2 in I (D) Br is at C1 in both cases
Q.44 Whichoffollowingis correctlymatched.
(A)
3
3
3
CH
|
CH
C
CH
|
OH

 , E1 reaction (B) CH3–CH2–CH2OH, E1cb reaction
(C)
3
3
3
CH
|
CH
C
CH
|
OH

 , thermalreaction (D) , E1 cb reaction
Q.45 Arrange reactivityofgivenalcoholinincreasing orderofeliminationreaction
(I)
2
2
2
2
2
NO
|
OH
CH
CH
CH
CH 

 (II)
2
2
2
3
NO
|
OH
CH
CH
CH
CH 


(III)
2
2
2
3
NO
|
OH
CH
CH
CH
CH 

 (IV) CH3–CH2–CH2–CH2OH
Select answer fromcodes given below:
(A) I, II, IV, III (B) I, II, III, IV (C) II, III, I , IV (D) II, III, IV, I

9. Q.46 

 
 KOH
.
alc
A, Ais
(A) (B) (C) (D) None is correct
Q.47 Major product obtained in reaction of 1-phenyl-2-bromo butane with NaOMe.
(A) (E)-1-phenylbut-1-ene (B) (E)-1-phenylbut-2-ene
(C) 1-phenyl-1-ethoxybutane (D) (Z)-1-phenylbut-2-ene
Q.48 2-Aminocyclohexane-1-olon treatment with HNO2 produces
(A) Cyclopentane carboxaldehyde (B) Cyclo hexane-1,2-diol
(C) 2-amino cyclohexene (D) Cyclohex-2-enol

10. EXERCISE–II
(Choose the correct option. One or more than one are correct)
Q.1 Whichalkylhalide undergo E2 elimination
(A) (B)
(C) (D)
Q.2 Inthegivenreaction:


 2
Br [X]
[X]is:
(A) (B) (C) (D)
Q.3
CHCOOH
|
|
CHCOOH
(maleic acid) canform:
(A) stereoisomer (B) geometricalisomer (C) chain isomer (D) functionalisomer
Q.4 Which canshow tautomerism?
(A) (B) CH3–CN (C) 3
||
CH
C
O
 (D)
Q.5 Whichareincorrect statements:
(A) and are enantiomers
(B)
H
|
CH
CH
C
CH
|
Cl
3
2
3

 and
3
2
3
CH
CH
|
H
C
Cl
|
H
C

 are enantiomers
(C)Argol(sodiumpotassiumtartarate) willshow opticalisomerism.
(D) CH3CHO onreaction with HCN gives racemic mixture.

11. Q.6 Whichis/are less acidic than Benzoic acid?
(A) CH3COOH (B) (C) (D) H2O
Q.7 Whichhave active methylene group?
(A) 3
2
3 CH
C
CH
C
CH
|
|
|
|
O
O



 (B) CH3–CH2–NO2
(C) Et
O
C
CH
C
CH
||
|
|
O
O
2
3 



 (D) CN
CH
C
|
|
O
2 

Q.8 Whichofthefollowing are not resonating structuresofeachother:
(A) (B)
(C) (D)
Q.9 Which ofthefollowing compounds yield most stable carbanionafter rupture of(C1–C2)bond:
(A)
2
1
CCl
C
CH
||
O
3
3 
 (B)
2
1
CBr
C
CH
||
O
3
3 
 (C)
2
1
CI
C
CH
CH
||
O
3
2
3 

 (D) noneofthese
Q.10
pyrrole (I) pyridine (II) aniline (III)
which is/are correct statements ?
(A) I is more basic than II (B) II is more basic thanI and III
(C) III is more basic than II (D) allare aromatic bases
Q.11 Whichis/areuntrue statement(s)?
(A) Protonationincreases electrophilic nature ofcarbonylgroup
(B) 
3
3SO
CF is better leaving group than 
3
3SO
CH
(C) Benzylcarboniumionis stabilised byresonance
(D) CCl3CH is unstable
Q.12 Identifythecorrect statment(s).
I II III IV
(A) I &III are antiaromatic (B) III &IV are non-aromatic
(C) II alone is aromatic (D) II &IV are non-aromatic

12. Q.13 Which haveacidic hydrogen?
(A) CH3COOH (B)
(C) CN
CH
C
CH
|
|
O
2
3 

 (D) NaNH2
Q.14 Which ofthe following maybe classed as an electrophilic reagent?
(A) BCl3 (B) 
4
NH (C) 3
H
C

(D) 
4
AlCl
Q.15 The acid strengthofsubstituted carboxylic acidsis knownto bedependent onthe natureand positionof
the substituent. Inthe following examples, anattempt has beenmade to arrange theacids inorder ofacid
strength, the strongest first. One ofthe series is incorrect–whichone?
(A) CH3.CH2CH(Cl).COOH > CH3.CH(Cl).CH2COOH > CH3.CH2.CH2.COOH
(B) NO2.CH2.COOH > HOCH2.COOH > CH3.COOH
(C) Cl3C.COOH > BrCH2.COOH > FCH2.COOH
(D) CH3.COOH > CH3.CH2.COOH > (CH3)3C.COOH
Q.16 Whichofthefollowing would not havea dipole moment?
(A) CCl4 (B) CH2Cl2 (C) trans-1,2-dichloroethene (D)
Q.17 Whichofthe following structures represent the lessstable tautomeric form?
(A) (B)
(C) (D)
Q.18 Whichofthe following compounds cannot exhibit keto-enoltautomerism?
(A) (B)
(C) C=O (D)
Q.19 Intautomerism
(A) a proton is moved around the molecule (B) electrons are moved around the molecule
(C) no actualmovement occurs (D) shift ofdouble bond occurs
Q.20 Which species is not aromatic?
(A) (B) (C) (D)

13. Q.21 Aromatic character is possible onlywhen
(A) sixelectrons are delocalized
(B) the molecule is cyclic and planar having delocalized (4n +2) electrons where n= 1,2,3....
(C) alternate sigma () &pie () bond are present.
(D) None is true
Q.22 Which reactswithAgNO3 to give ppt.?
(A) (B) CH=CH–CH2Br
(C) (D)
Q.23 Inwhichoffollowing compound chiralcenter is not affectedonheating.
(A)
OH
|
COOH
CH
CH3 
 (B)
(C)
OH
|
COOH
CH
CH
CH 2
3 

 (D)
COOH
CH
|
CHCOOH
CH
2
3

Q.24 Which are correct statements?
(A) methylmalonic acid is converted into propanoicacid onheating
(B) succinicacid forms succinic anhydrideonheating
(C) 3-hydroxypropanoic acid forms Lactideon heating
(D) COOH
CH
C
CH
|
|
O
2
3 
 forms acetone onheating
Q.25 Select incorrect statements:
(A) and both give colour withneutralFeCl3 solution
(B) 2-pentanone and 3-pentanone are metamers
(C) product formedwhenbenzaldehyde reacts withhydroxylamineshows opticalisomerism
(D) 1,2-dibromocyclohexane showsgeometricaland opticalisomerism.
Q.26 C5H8O4 (A) 

 C4H8O2 (B)



 
 lime
Soda
(C)
C is hydrocarbonoccupying 0.509 litre per g approximately. HenceAand B are:
(A) methylmalonicacid, propanoic acid (B) succinic acid, succinic anhydride
(C) Dimethylmalonicacid, 2-Methylpropanoic acid (D) EthylMalonicacid, Butanoic acid
Q.27 
 


O
H3
products canbe: (Both stable &unstable form)
(A) CH3CH(OH)2, CH3CH(OH)COOH (B) CH3CHO, CH3CH(OH)COOH
(C) CH3CH2COOH, CH3CH2OH (D) CH3CH(OH)COOH, CH3CH2OH

14. Q.28 Products formed when HCladds to 2,4- hexadiene is:
(A) 4-chloro-2-hexene (B) 2-chloro-3-hexene
(C) 2-chloro-4-hexene (D) 1-chloro-2-hexene
Q.29 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.30 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.31 Match List-I withList-II for relative rates ofgiven 2
N
S reaction& select the correct answer fromthe
codes given below
Z–CH2Br +

O
CH 3  Z–CH2–OCH3 + 
Br
List-I List-II
(A) H– (P) 0.1
(B) CH3– (Q) 3
(C) C2H5– (R) 1
(D) (S) 100

15. Q.32 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.33 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

16. EXERCISE–III
Q.1 Because the SN1 reaction goes though a flat carbocation, we might except anopticallyactive starting
materialto give a completelyracemized. Inmost cases, however, SN1 reactionsactuallygivemoreofthe
inversionproduct. Ingeneral, as the stabilityofthe carbocation increases, theexcess inversion product
decreases. Extremelystablecarbocations give completelyracemic products. Explainthese observation.
Q.2 The reactionofan amine withan alkylhalide gives anammoniumsalt.


N
R3
+ R'–X 

N
R3
– R' X–
amine alkyl halide ammoniumsalt
TherateofthisSN2reactionissensitiveto thepolarityofthesolvent. Considerthenatureofthetransition
state, and explainwhythis reaction should be sensitive to the polarityofthe solvent. Predict whether it
willbe faster or slower in a more polar solvent.
Q.3 There isanoverall29-folddifferenceinreactivityof1-chlorohexane,2-chlorohexanetowards potassium
iodide inacetone.
(a) Which one is the most reactive? Why?
(b) Two oftheisomers differ byonlya factor of2 inreactivity. Whichtwo are these?Whcihoneis themore
reactive? Why?
Q.4 The compound KSCN is a source of thiocyanate ion.
Write the two most stable Lewis structuresfor thiocyanate ionand identifythe atomin eachthat bears a
formalchargeof–1.
Q.5 WhenCH3MgBr react with5-chloro-2-pentanone, cyclic etheris formed instead ofalocohol. Explain.
Q.6 The dichlorocarbenereactswithelectronrichspecies likephenolwhereas it doesn’t reactswithbenzene
explain.
Q.7 Whyiseliminationpreferredtohemiacetalformationintheacidcatalysedcyclisationofthisketone?




H
Q.8 Draw mechanisms for these reactions, explaining whythese particular products are formed.

 

MeOH
Q.9 The reactionofcyclopentylbromide withsodiumcyanide to givecyclopentylcyanide
water
ethanol
NaCN


 

Cyclopentyl bromide Cyclopentylcyanide
proceeds faster ifa smallamount ofsodiumiodide is added to the reaction mixture. Canyou suggesta
reasonable mechanismto explainthe catalytic functionofsodiumiodide?
Q.10 The reactionof2,2-dimethyl-1-propanolwith HBr is veryslow and gives 2-bromo-2-methyl-propane
as the major product.
3
C
65
HBr
2
3
3
CH
|
OH
CCH
CH
|
CH


 

Br
|
CH
CCH
CH
|
CH
3
2
3
3
Give a mechanisticexplanationfor these observations.

17. Q.11 1-Bromobicyclo[2.2.1]heptane(thestructureofwhichisshown)isexceedinglyunreactivetowardsnucleophilic
substitutionbyeithertheSN1orSN2mechanism.
1-Bromobicyclo [2.2.1] heptane
Q.12 Giveamechanism to explain thetwo productsformed in thefollowing reaction.


 


h
,
NBS +
3-methyl-1-butene not rearranged rearranged
Q.13 Comment on the selectivity, (that is, saywhat else might have happened & whyit didn’t)shown in this
grignard additionreactionused inthemanufacture ofanantihistamine drug,A.
Q.14 Select the alkylhalide and a nucleophile that willgive each ofthe following products.
(a) CH3 – CH2 – CH2 – NH2 (b) CH3 – CH2 – O – CH2– CH3
(c) CH  C – CH2 – CH2 – CH3 (d) (CH3)2CHS(CH3)2
(e) C6H5 – O – CH2 – CH3
Q.15 Identifythe product in eachofthefollowing reactions :
(a)
Cl
|
ClI
H
C
CH
CHCH
CH
ClCH 10
5
acetone
)
mole
1
(
NaI
3
2
2
2 


 

(b) BrCH2CH2Br + NaSCH2CH2SNa  C4H8S2
(c) ClCH2CH2CH2CH2Cl + Na2S  C4H8S
Q.16 Writethestructure ofthe principalorganic product to beexpected fromthe reactionof1-bromopropane
witheachofthe following :
(a) Sodiumiodide in acetone.
(b) Sodiumacetate ( CONa
CH
|
|
O
3
) inacetic acid.
(c) Sodiumethoxide in ethanol.
(d) Sodiumcyanideindimethylsulfoxide.
(e) Sodiumazidein aqueous ethanol
(f) Sodiumhydrogensulfideinethanol
(g) Sodiummethanethiolate (NaSCH3)inethanol.
Q.17 Predict the products ofthe following SN2reaction:
(a) C6H5 – CH2– CH2 –Br 
 

NaCN
(b) Cl 

 
 3
NaSCH

18. (c) CH3 – (CH2)8– CH2– Cl acetone
NaI


 (d) CH3I 
(e) HO – CH2 – CH2 – CH2 – CH2 – Cl 
 
NaOH
Q.18 Draw eachofthe following reactionina waythat clearlyshow the stereoisomerismofthe products.
(a)
3
2
2
S
methanol
3
3
CH
CH
|
ONa
CH
Br
C
CH
|
H
N



 



 (b)
7
3
1
S
3
2
3
3
H
C
|
OH
CH
Br
C
CH
CH
|
CH
N







(c) 1
SN
NaSH

 

Q.19 Completethefollowingreactions. Giveallpossibleproductsineachcase. Givemechanismofthereactions.
(a) 


 

O
Ag
Moist 2 (b) CH2
– Cl 

 


/
HOH
Q.20 What products would be formed inthese reactions ?
(a) Ph – C  CH
Cl
NH
)
iii
(
CO
Ph
)
ii
(
EtMgBr
)
i
(
4
2



 
 A (b)
O
H
/
H
)
iii
(
,
CO
)
ii
(
PhLi
)
i
(
2
2







 
 B
Q.21 B
A
Na
OH
C
C
Cl
|
|
O
2
2 CH
CH
3



 





 . Find outA& B.
Q.22 Give product and suggest mechanismforthese reactions.
(i) ?
Cl
MeOCH
BuLi
2

 
 BuOK
CHBr
t
3

 
 ? (ii)
Zn


?
Ph – CH = CH2
Q.23 CHCl2
F is found to react more slowly than CHCl3
in alkaline hydrolysis with plausible mechanism.
Illustratethis phenomenon.
Q.24 Dr. DonT. Doit wanted to synthesizethe anesthetic 2-ethoxy-2-methylpropane. Heused ethoxide ion
and 2-chloro-2-methylpropane for his synthesis and ended up with very little ether. What was the
predominant product ofhis synthesis ?What reagent should he have used ?
Q.25 When ethylbromide is added to potassiumt-butoxide, the product is ethylt-butylether.
CH3CH2 – Br + (CH3)3C – O– +K  (CH3)3C – O – CH2CH3
ethylbromide potassiumt-butoxide ethylt-butylether
(a) What happens to the reaction rate ifthe concentration ofethylbromide is doubled ?
(b) What happensto the rate ifthe concentrationofpotassiumt-butoxide id tripled andthe concentrationof
ethylbromide is doubled ?
(c) What happens to the rate if the temperature is raised ?
Q.26 SolutionA was prepared by dissolving potassium acetate in methanol Solution B was prepared by
adding potassiummethoxide to acetic acid. Reaction of methyl iodide either with solutionAor with
solution B gave the same major product. Why? What was this product?

19. Q.27 Select thecombinationofalkylbromide and potassiumalkoxide that would be the most effective in the
synthesisofthefollowingethers :
(a) CH3OC(CH3)3 (b) OCH3 (c) (CH3)3CCH2OCH2CH3
Q.28 cis-1-Bromo-2-tert-butylcyclohexaneandtrans-1-bromo-2-tert-butylcyclohexanebothreact withsodium
ethoxide in ethanolto give 1-tert-butylcyclohexene. The cis isomer reacts muchmore rapidlythan the
transisomer. Explain.
Q.29 Withthehelp offollowing datashow HBr exhibits the peroxide effect.
H1
0
H2
0
H–X X

+ CH2
= CH2
 X CH2
– C

H2
XCH2
–C

H2
+ H–X  XCH2
CH3
+ X


HCl –67 + 12.6
HBr –25.1 – 50.2
HI +46 –117.1
All are in kJ mole–1
.
Q.30 Formulate the reactions between but–1–ene inpresence ofsmallamount ofbenzoylperoxide &
(i) CCl4
(ii) CBrCl3
Give your reasons.
Q.31 p-Amino benzaldehyde behaves like an amide as is evident bythe fact that it is not readily attackedby
the nucleophile at the carbonylcarbon. Explain.
Q.32 Explainthefollowing:
(a) 3-pentanol reacts with HBr to give a mixture of3 &2- bromopentane. The exact composition of the
mixture depends uponwhether gaseous or aqueousHBr is used.
(b) Hydration of 3-phenyl-1-butene in dil H2SO4 is not a satisfactory method for preparing
3-phenyl-2- butanol
Q.33 CH2 = CH – CH2
3
2
NaHCO
Br
2 OH
C
CH
|
|
O





This type ofreactionis called “bromolactonistaion”. Suggest a mechanism.
Q.34 Write a reasonable and detailed mechanismforthe following transformation.
4
2SO
H
.
conc

 
 + H2
O
Q.35 Wesawthat acid-catalyzed dehydrationof2,2-dimethyl-cyclohexanolafforded 1,2-dimethylcyclohexene.
To explainthisproduct we must writea mechanismfor the reactioninwhich a methylshift transforms a
secondarycarbocationto atertiaryone.Another product ofthedehydrationof2,2-dimethylcyclohexanol
is isopropylidencyclopentane.Write a mechanismto rationalize its formation.
heat
H



+ C(CH3)2
2,2-Dimethylcyclohexanol 1,2-Dimethylcyclohexene Isopropylidenecyclopentane

20. Q.36 When2-bromo-2,3-dimethylbutanereacts witha baseunder E2 conditions, two alkenes (2,3-dimethyl-
1-butene and 2,3-dimethyl-2-butene) are formed.
(a) Which ofthefollowing bases would give the highest percentage ofthe 1-alkene ?
(b) Which would givethe highest percentage ofthe 2-alkene “
3
3
3
CH
|
CO
CH
|
CH

3
2
2
3
3
2
CH
CH
|
CO
CH
CH
|
CH
CH

CH3CH2O–
3
2
3
3
CH
|
CO
CH
CH
|
CH

Q.37 The followingreactiontakes place undersecond-order conditions(strongnucleophile), yet the structure
oftheproduct shows rearrangement.Also, the rate ofthis reactionis severalthousandtimes fasterthan
therateofsubstitutionofhydroxideionon2-chlorobutaneundersimilarconditions.Proposeamechanism
to explaintheenhancedrateandrearragement observed inthisunusualreaction. (“Et”isthe abbreviation
for ethyl.)
Cl
|
CH
CH
CH
C
H
|
N
Et
3
2
2
2





 


OH
OH
|
Cl
CH
CH
CH
C
H
|
NEt
3
2
2
2






Q.38 Give the structuresofallpossible productswhen2-chloro-2-methylbutane reacts bythe E1 mechanism.
Q.39 Solvolysis of1,2-dimethylpropylp-toluenesulfonate inaceticacid (75°C) yields fivedifferent products :
three arealkenesand two are substitutionproducts. Suggest reasonablestructures forthesefiveproducts.
Q.40 Solvolysis of2-bromo-2-methylbutane inacetic acid containing potassiumacetate gavethree products.
Identifythem.
Q.41 (a)Writethe structures orbuildmolecularmodelsofalltheisomeric alkylbromideshaving themolecular
formula C5H11Br.
(b) Which one undergoes E1 eliminationat thefastest rate ?
(c) Which one is incapable ofreacting bythe E2 mechanism?
(d) Which one can yield onlya single alkene onE2 elimination ?
(e) For whichisomersdoes E2 eliminationgivetwo alkenes that are not constitutionalisomers ?
(f) Which one yields the most complexmixture ofalkenes onE2 elimination ?
Q.42 Evidence has beenreported in the chemicalliterature that the reaction
(CH3CH2)2CHCH2Br + KNH2  (CH3CH2)2C = CH2 + NH3 + KBr
proceeds bythe E2 mechanism. Use curved arrow notation to represent the flow ofelectrons for this
process.
Q.43 The givencompoundgive mixture ofsixproductsontreatment withCH3OH. Writestructures ofallfive
products and give mechanismofthe reaction.


 

OH
CH3 A + B + C + D + E+ F
Q.44 Outlineanefficient synthesisofeachofthe following compoundsfromthe indicatedstartingmaterialand
anynecessaryorganicor inorganic reagents :
(a) Cyclopentylcyanide fromcyclopentane.
(b) Cyclopentylcyanide fromcyclopentene.

21. (c) Cyclopentylcyanide fromcyclopentanol.
(d) Isobutyliodidefromisobutylchloride.
(e) Isobutyliodidefromtert-butylchloride.
(f) Isobutylazidefromisopropylalcohol
Q.45 Indicate the major alkene produced byeachofthe following
(a)
3
/
K
O
CH
3
2
2
3
CH
|
CH
C
CH
CH
CH
|
Br
3



 




 



(b)
3
3
3
2
2
3
3
CH
|
H
O
)
CH
(
N
C
CH
CH
CH
|
CH









(c)
3
3
2
3
3
3
CH
|
H
O
CH
CH
C
N
)
CH
(
|
CH








(d) 



 







K
O
C
)
CH
(
3
2
2
3
3
3
CH
CH
CH
CH
CH
|
F
Q.46 Choose the compound of molecular formulaC7H13Br that gives each alkene shownas the exclusive
product ofE2elimination.
(a) (b) (c)
(d) (e) CH = CH2 (f)
(g) C(CH3)3
Q.47 What willbe the products (A, B, C) in the folowing reaction?
Give a mechanismfor each ofthe reactions.
Q.48 Identify(A)to (D) in thegiven reactionsequence.
CH3
– CH2
– CH3 

 

hv
/
Br2 (A)



 
 KOH
alc
(B)
Peroxide
HBr

 
 (C)
DMF
LiF


 (D)
Q.49 Identify(A) to (E) inthegivenreactionsequence
CH3
–CH2
–Br 

 
 CuX
/
Li
(A) 



 


 Br
CH
CH 2
3 (B) 

 
 hv
/
Cl2 (C)+(D)+(E) 


 



K
O
C
)
CH
( 3
3
(F)+(G)+(H).

22. Q.50 Completethefollowing reactions :
(a) )
B
(
)
A
(
CH
C
)
CH
(
C
CH
|
|
|
|
O
O
H
)
ii
(
/
NaOH
/
I
)
i
(
3
4
2
3
2





 







(b) )
D
(
)
C
(
CH
C
|
|
O
H
)
ii
(
NaOH
/
Br
)
i
(
3
2





 

 
(c) CHOH – CH3 





 

H
)
ii
(
HOH
/
CaOCl
)
i
( 2 (E) + (F)
(d)
Cl
|
CH
CH
CH
CH 2
F
/
NaOH
3
2
3 

 



 G + H
Q.51 Completethefollowing reactions
(a)
Br
|
HOH
NaCl
CH
CH
H
C is
Electrolys
3
5
6 


 




 Asweet smelling liquid
(b) C6H5 – 

 

NaOH
.
aq
Q.52 (i)What are the products ofthe following reactions ?
(a) PhCH = CHCH3 + HBr A (b) + HI  B
(c) + HBr 

 

Peroxide
C (d) + HCl D
(ii) What are the products ofthefollowing reactions ?
(a) PhC  CH + Br2  (b) CH3CH2CH = CH2 O
H
Cl
2
2



(c) O
H
Br
2
2


 (d) O
H
Br
2
2



O
H
NaOH
2

 

Q.53 CH3CH2CH2Cl 

 

KOH
.
alc
A 

 
 2
2Cl
SO
B 

 

O
Et
/
Mg 2 C
Cl
NH
.
aq
)
ii
(
CH
C
CH
)
i
(
|
|
O
4
3
3




 
 

D 

 


/
SO
H 4
2
E.

23. EXERCISE–IV (A)
Q.1 Reaction of R–CO–NH2 with a mixture of Br2 and KOH gives R–NH2 as the main product. The
intemediates involvedinthis reactionare:
(A) R–CO–NHBr (B) RNHBr
(C) R–N=C=O (D) R.CO.NBr2
Q.2 Whichoneofthe following hasthe smallest heat ofhydrogenationper mole?
(A) 1-Butene (B) trans-2-Butene
(C) cis-2-Butene (D) 1,3-Butadiene
Q.3 Inthefollowing compounds:
The orderofacidityis:
(A) III > IV > I > II (B) I > IV > III > II (C) II > I > III > IV (D) IV > III > I > II
Q.4 The reaction ofCH3– CH=CH OH withHBr gives:
(A) CH3CHBrCH2 OH (B) CH3CH2CHBr OH
(C) CH3CHBrCH2 Br (D) CH3CH2CHBr Br
Q.5 Asolutionof(+) 1-chloro-1-phenylethane in toluene racemizes slowlyinthe presence ofsmallamount
ofSbCl5 due to formationof:
(A) carbanion (B) carbene (C) free radical (D) carbocation
Q.6 Anaromaticmolecule will:
(A) have 4n  electrons (B) have (4n+2)  electrons
(C) be planar (D) be cyclic
Q.7 The enolformofacetone, after Prolonged treatment with D2O, gives:
(A) 2
3 CH
C
CH
|
OD

 (B) 3
3 CH
C
CH
|
|
O

 (C) D
CH
C
CH
|
OH
2
2 
 (D) 3
2 CD
C
CD
|
OD


Q.8 Amongst thefollowing, the most basiccompound is:
(A) C6H5NH2 (B) p-NO2–C6H4NH2 (C) m-NO2–C6H4NH2(D) C6H5CH2NH2
Q.9 An SN2 reaction at anassymetricalcarbon ofa compound always gives:
(A) enantiomerofthe substrate (B) a product with opposite opticalrotation
(C) a mixture ofdiastereomeres (D) a single stero isomers

24. Q.10 The correct orderofbasicities ofthefollowing compounds is:
CH3CH2NH2 (CH3)2NH
2
3CNH
CH
|
|
O
(1) (2) (3) (4)
(A) 2 > 1 > 3 > 4 (B) 1 > 3 > 2 > 4 (C) 3 > 1 > 2 > 4 (D) 1
Q.11 Identifythe correct orderofreactivityinelectrophilic substitutionreactionofthe following compounds:
(A) 1>2>3>4 (B) 4>3>2>1 (C) 2>1>3>4 (D) 2>3>1>4
Q.12 Left to right sp2, sp2, sp, sp hybridization is present in:
(A) H2C = CH–CN (B) H2C=C=CH–CH3 (C) HCC–CCH (D) HCC–CH=CH2
Q.13 Maximumdipole moment willbe of:
(A) CCl4 (B) CHCl3 (C) CH2Cl2 (D) CH3Cl
Q.14
when X is made to react with 2 eq. ofNaNH2 the product formed will be:
(A) (B)
(C) (D)

25. Q.15 Order ofrate ofreactionoffollowing compound with phenylmagnesiumbromide is:
)
I
(
O
|
|
Ph
C
Ph 

)
II
(
O
|
|
H
C
Me 

)
III
(
O
|
|
Me
C
Me 

(A) I > II > III (B) II > III > I (C) III > I > II (D) II > I > III
Q.16
Correct order ofacidic strengthis:
(A) x > y > z (B) z > y > x (C) y > z > x (D) x > z > y
Q.17 1-Bromo-3-chloro cyclobutane onreactionwith2-equivalent ofsodiumin ether gives
(A) (B) (C) (D)
Q.18 )
solution
.
aq
(
)
excess
(
COONa
CH3





 

(A) (B)
(C) + CH3COOH (D) + H2SO3
Q.19 Conversionofcyclohexanolinto cyclohexene ismost effective in
(A) concentrated H3PO4 (B) concentrated HCl
(C) concentrated HCl/ ZnCl2 (D) concentrated HBr
Q.20 Ph – MgBr + CH3
3
3
CH
|
OH
C
|
CH

  A
A
(A) (B)
3
3
3
CH
|
OPh
C
CH
|
CH

 (C) (D)
3
3
3
CH
|
Ph
C
CH
|
CH



26. Q.21 For 1-methoxy-1,3-butadiene, whichofthe following resonating structure is theleast stable?
(A) 3
2 CH
O
CH
CH
CH
C
H 






(B) 3
2 CH
O
CH
CH
CH
C
H 






(C) 3
2 CH
O
CH
CH
CH
C
H 






(D) 3
2 CH
O
CH
CH
CH
C
H 






Q.22
on hydrolysis inpresence ofacetone
(K) (L)
(M)
(A) K & L (B) only (C) M only (D) K & M
Q.23 Whenbenzenesulfonicacid andp-nitrophenolaretreated withNaHCO3, thegases released respectively
are
(A) SO2, NO2 (B) SO2, NO (C) SO2, CO2 (D) CO2, CO2
Q.24 CH3NH2 + CHCl3 + KOH  Nitrogen containing compound + KCl + H2O. Nitrogen containing
compound is
(A) CH3-CN (B) CH3-NH-CH3 (C)


 C
N
CH
—
3 (D)
—
3 C
N
CH 

Q.25 (I) 1,2-dihydroxybenzene (II) 1,3-dihydroxybenzene
(III) 1,4-dihydroxybenzene (IV) Hydroxybenzene
The increasing orderofboiling points ofabove mentioned alcohols is
(A) I < II < III < IV (B) I < II < IV < III (C) IV < I < II < III (D) IV < II < I < III

27. Question No. 26 to 28 ( 3 questions)
Comprehension I
RCONH2 is converted into RNH2 bymeans ofHofmannbromamide degradation.
In this reaction, RCONHBr is formed fromwhichthis reactionhas derived its name. Electron donating
group at phenylactivates the reaction. Hofmanndegradationreactionis anintramolecular reaction.
Q.26 How can theconversion of(i) to (ii) be brought about?
(A) KBr (B) KBr + CH3ONa (C) KBr + KOH (D) Br2 + KOH
Q.27 Whichis the rate determining step inHofmannbromamide degradation?
(A) Formationof(i) (B) Formationof(ii) (C) Formationof(iii) (D) Formationof(iv)
Q.28 What arethe constituent amines formedwhenthe mixture of(i) and (ii) undergoesHofmannbromamide
degradation?
(A)
(B)
(C)
(D)

28. EXERCISE–IV (B)
Q.1 CH3CH2CHCl2 

 

KOH
.
aq ?
Q.2 C6H6+ (CH3)2CHCH2Cl 
 
 3
AlCl ?
Q.3 COO
ion
mononitrat
SO
H
/
HNO 4
2
3




 
 ?
Q.4 Draw the stereochemicalstructure ofthe products inthe following reaction:
2
S
NaOH
N

 
 ?
Q.5 Completethe following,giving the structures oftheprincipalorganic products:
(a) + KNH2  A
A
(b) + CHBr3 + t – BuOK  B
(c) ClCH2CH2CH2COPh + KOH + MeOH  C
Q.6 Write the intermediatesteps for each ofthe following reaction.
(i) C6H5CH(OH) CCH 
 


O
H3
C6H5CH = CH–CHO
(ii) 



H
Q.7 Each ofthefollowing reactiongives two products. Write the structure ofthe products.
(a) C6H5CH2CHClC6H5 


 


,
KOH
.
Alc
(b) CH3CONHC6H5 
 

Fe
,
Br2
Q.8 Out ofanhydrousAlCl3 andhydrousAlCl3 whichis more soluble indiethylether?Explainwithreason.
Q.9 Match Ka values withsuitable acid:
Ka Acid
(i) 3.3 × 10–5 (a)
(ii) 4.2 × 10–5 (b)
(iii) 6.3 ×10–5 (c)
(iv) 6.4 × 10–5 (d)
(v) 30.6 × 10–5 (e)

29. Q.10 Give resonatingstructuresoffollowingcompound.
Q.11 Which ofthe following is more acidic and why?
Q.12 Predict whether the following molecules are iso structuralor not. Justifyyour answer.
(i) NMe3 (ii) N(SiMe3)3
Q.13 Give reasons:
(a) (i) 


 

.)
aq
(
OH
H
C 5
2 acidic solution
(ii) 


 

.)
aq
(
OH
H
C 5
2 neutral
(b) (i) 


 

.)
aq
(
NaOH
F (liberated)
(ii) 


 

.)
aq
(
NaOH Fis not liberated
(c) (i)
4
2
3
SO
H
.
Conc
HNO
.
Conc



 
 +
(ii)
4
2
3
SO
H
.
Conc
HNO
.
Conc



 

(d)
2
H
of
moles
3
C
/
Pd

 
 is formed but not

30. Q.14 





smell
pungent
and
fumes
Brown
B 


 

 2
MnO
NaBr
A 


 
 3
HNO
.
Conc
C(intermediate) D(Explosive product)
FindA, B, C and D.Also write equationsAto B andAto C.
Q.15 obs =  i
ix
where i is the dipole moment ofstable conformer and xi isthe fraction ofthat conformer.
(a) Write stable conformer for Z– CH2– CH2– Z in Newman's projection. If solution = 1.0 D and mole
fraction ofantiform= 0.82, find Gauche.
(b) Write most stablemeso conformer of
CHDY
|
CHDY
If (i) Y = CH3 about C2 – C3 rotation and (ii)Y = OH about C1 – C2 rotation.

31. ANSWER KEY
EXERCISE–I
Q.1 C Q.2 B Q.3 B Q.4 B Q.5 C Q.6 D Q.7 A
Q.8 D Q.9 D Q.10 A Q.11 D Q.12 C Q.13 B Q.14 C
Q.15 B Q.16 B Q.17 A Q.18 D Q.19 C Q.20 D Q.21 C
Q.22 A Q.23 B Q.24 B Q.25 A Q.26 C Q.27 C Q.28 D
Q.29 C Q.30 D Q.31 B Q.32 A Q.33 C Q.34 C Q.35 C
Q.36 C Q.37 B Q.38 B Q.39 C Q.40 A Q.41 D Q.42 A
Q.43 C Q.44 A Q.45 C Q.46 A Q.47 A Q.48 A
EXERCISE–II
Q.1 AB Q.2 D Q.3 ABCD Q.4 ABC Q.5 AB
Q.6 AD Q.7 ACD Q.8 CD Q.9 A Q.10 BD
Q.11 D Q.12 AC Q.13 ABC Q.14 AC Q.15 C
Q.16 AC Q.17 ABC Q.18 D Q.19 AD Q.20 B
Q.21 D Q.22 BD Q.23 ABD Q.24 ABD Q.25 C
Q.26 CD Q.27 AB Q.28 AB Q.29 A  3,B  ,C  1,D  2
Q.30 A  2, B  1, C  4, D  3 Q.31 (A) – S; (B) – Q; (C) – R; (D) – P
Q.32 (A) – Q; (B) – S ; (C) – R; (D) – P Q.33 (A) – Q; (B) – R ; (C) – P; (D) – Q
EXERCISE–III
Q.2 Faster Q.5 Q.13
Q.14 (a) CH3CH2CH2Cl + NH3 ; (b) CH3CH2ONa + CH3CH2Cl ; (c) HCCNa + CH3CH2CH2–Cl
(d) Me2CH–Cl + Me2S ; (e) C6H5ONa + CH3CH2–Cl
Q.15 (a)
Cl
|
CH
CH
CH
CH
ICH 3
2
2
2 
 ; (b) ; (c)
Q.16 (a) ; (b) ; (c) ; (d) ; (e) ; (f) ;
(g)
Q.17 (a) C6H5–CH2–CH3–CN, (b) , (c) CH3–(CH2)9–I, (d) , (e)
Q.18 (a)
3
2
3
3
CH
CH
|
CH
C
O
CH
|
H

 ; (b)
Pr
|
OMe
C
Et
|
Me

 +
Pr
|
Et
C
MeO
|
Me

 , (c) +

32. Q.20 (a)
OH
|
Ph
C
C
C
Ph
|
Ph



 ; (b) Q.21 A: 2
CCl

 B :
Q.22 (i) & ; (ii) Q.26 MeCOOMe
Q.36 (a) Et3CO ; (b) EtO Q.40
C
|
C
C
C
C 

 ,
C
|
C
C
C
C 

 ,
C
|
C
C
C
C
|
OAC



Q.41 (b)
C
|
Br
C
C
C
|
C


 ; (c)
C
|
C
C
C
Br
|
C


 ; (d) C–C–C–C–C–Br ; (e)
Br
|
C
C
C
C
C 



(f)
Br
|
C
C
C
C
C 



Q.45 (a)
C
|
C
C
C
C
C 


 ; (b) C
C
C
C
C
|
C



 ; (c) C
C
C
C
|
C


 ; (d) C–C–C–C=C
Q.46 (a) ; (b) ; (c) ; (d) ; (e)
(f) , (g)
Q.47 (A) RCH2CH2SR (B) RCHBrCH2CCl3 (C) RCHClCH2CCl3 Q.48 CH3–CH2–CH2–F
Q.50 (a) CHI3+(CH2)4(COOH)2, (b) CHBr3+ , (c) CHCl3+ , (d) CHF3 + EtCOONa
Q.51 (a) CHCl3, (b) PhCHO
Q.52 (i) (a)
Br
|
Et
CH
Ph 
 , (b) Me2C(I)–Et, (c) , (d)
(ii) (a) , (b)
OH
|
Cl
CH
CH
Et 2


 , (c) , (d)
Q.53 Me2C=CH–CH=CH2

33. EXERCISE–IV (A)
Q.1 A,C Q.2 D Q.3 D Q.4 B
Q.5 D Q.6 B,C,D Q.7 D Q.8 D
Q.9 D Q.10 B Q.11 C Q.12 A
Q.13 D Q.14 C Q.15 B Q.16 D
Q.17 C Q.18 C Q.19 A Q.20 A
Q.21 C Q.22 A Q.23 D Q.24 D
Q.25 C Q.26 D Q.27 D Q.28 B
EXERCISE–IV (B)
Q.1 CH3CH2CHO Q.2 Q.3
Q.4
3
5
2
CH
|
OH
C
H
|
H
C

 Q.5 (A) PhCCPh, (B) , (C)
Q.6
2
5
6
O
H
5
6
H
5
6
OH
OH
|
|
CH
C
CH
H
C
CH
C
CH
H
C
CH
C
CH
H
C 2







 











2
5
6
O
H
5
6
OH
|
H
C
C
CH
H
C
CH
C
CH
H
C 2






 




 –H+
2
5
6
OH
|
CH
C
CH
H
C 

 C6H5–CH=CH–CHO
(ii)
Q.7 (a) (b) +
Q.8 AnhydrousAlCl3 is morestable thenhydrousAlCl3 becauseit ishaving vacant 3porbitalofAlwhichcan
accept lone pair ofelectrons fromoxygenofdiethylether.
Q.9 (i)–(d), (ii)–(b), (iii)–(a), (iv)–(c), (v)–(e)

34. Q.10
Q.11 ismore acidic as overalleffect of–Fiselectron withdrawing, so loss ofportionis easierfromthis
compound.
Q.12 Not. NMe3 is trigonalpyramidalwhile N(SiMe3)3 is trigonalplanar due to back bonding.
Q.13 (a) (i)
3
5
2
6
5
3
CH
|
)
acid
(
HBr
H
OC
C
C
H
|
CH


 ; (ii) no reaction due to partialdouble bond character
(b) (i) + F– is liberated ; (ii) Bimomecular mechanism is not possible in (ii) case
(c) (i) due to presence oflone pair ofnitrogen atomNO group is electron denating and ortho, para
directing
(ii) NO2 group is electron withdrawing and meta directing
(d) Due to reduction ofcentralring, three fourmembered antiaromatic rings become stable while on
recuction ofterminalring onlyone antiaromatic ring can be stabilized.
Q.14 (A) H2SO4, (B) Br2, (C) 
2
NO , (D)
Q.15 (a) Gauche= 5.55 D ; (b) (i) , (ii)