1. ORGANICCHEMISTRY
Daily Practice Problems
CLASS : XIII (ALL) DPP. NO.-20
Time : 90 Min. Max. Marks : 54
Q.1
3
2
2
2
2
3
3
CH
|
OH
CCH
CH
CH
CH
CH
|
CH




 
 4
2SO
H
.
conc
Major product is: [2]
(A*) CH3
CH2
CH2
CH2
CH= (B)
3
2
2
2
2
3
2
CH
CH
|
C
CH
CH
CH
CH
|
|
CH
(C)
3
2
2
2
3
CH
|
C
CH
CH
CH
CH  (D)
3
3
2
2
2
3
CH
|
CH
CH
C
CH
CH
CH
CH 

Q.2
ether
dry
LAH

 
 A
A 
 
 3
PBr
B 



 

KOH
Alcoholic
C
What are Ato C ? [3]
[Sol. (A) (B) (C) ]
Q.3 AssignAto D in the given reaction sequence [4]





 

,
AgOH
)
ii
(
)
excess
(
I
CH
)
i
( 3
A
A





 

,
AgOH
)
ii
(
)
excess
(
I
CH
)
i
( 3
B
[Sol. A = B = MeOH ]
Q.4 How willyou convert cyclohexane into benzeneinfour steps. [3]
[Sol.




h
Br2 

 
 KOH
alc
excess
NBS

 
 

 
 KOH
alc ]
Q.5 PhOCH2Cl + Ph3P + tBuO—K+  A (C25H21P) [3]
A + ethyl methyl ketone  Ph3P = O + B (C11H14O)
B + dilute aqueous acid  C (C5H10O)
What are Ato C?
[Sol. A = Ph3P = CHOPh B = C =
3
5
2
CH
|
H
C
CH
H
C
|
|
O


 ]

2. Q.6 Completethefollowing reactions.
(a) + PPh3  A + B
(b) ClCH2COMe 
 

P
Ph3 A 


 

EtOH
EtONa B [4]
[Sol. (a) A = CH2 = CHMe + Ph3P = O = B
(b) A =

Cl
)
COMe
CH
P
Ph
( 2
3

B = CHC–Me ]
Q.7 Give structure ofAto J. [9]


 

reduction
A(C9H17ON, an alcohol)
A + heat  B (C9H15N)
B + CH3I + Ag2O  C (C10H19ON)
C + heat  D (C10H17N)
D + CH3I + Ag2O  E (C11H21ON)
E + heat  F (C8H10)
F + Br2  G (C8H10Br2) [Thermodynamicallycontrolled pot]
G + Me2NH  H (C12H22N2)
H + MeI + Ag2O  I (C14H30O2N2)
I + heat  J (C8H8)
[Sol. (A) (B) (C) (D)
(E) (F) (G) (H)
(I) ]
Q.8(a)Complete thefollowing reactions.
(i) PhCH=CHCH2PPh3
+Cl— 
 
EtOLi
A 

 

PhCHO
B + C
(ii) Ph3P + (i) ClCH2COMe  D 

 
 3
2CO
Na
E 

 

PhCHO
F.
. [6]
(b) Rate law for substitutionreaction of2-bromobutnae with

OH in75% ethanol&25% water at 30°C is
rate = 3.20 × 10–5 (2-bromobutane) (OH–) + 1.5 × 10–6 (2-bromobutane) what percent of reaction
take place by SN2 when [OH–] = 1.00 m.
[Sol. (a) (i) A = PhCH = CHCH2= PPh3
B = Ph–CH=CH–CH=CH–Ph
C = Ph3PO

3. (ii) D =

Cl
)
COMe
CH
P
Ph
( 2
3

E = Ph3P = CHCOMe
F = Ph–CH=CHCOMe
(b) % by 2
N
S =
1
2
2
N
N
N
S
S
S

× 100
=
e]
Bromobutan
2
[
10
5
.
1
]
00
.
1
e][
bromobutan
2
[
10
20
.
3
100
]
00
.
1
e][
bromobutan
2
[
10
20
.
3
6
5
5











= 5
5
10
15
.
0
10
20
.
3
10
20
.
3
5






 × 100 = 96% ]
Q.9 Ei


Whichofthe following product cannot be obtained bythis reaction. [2]
(A) (B) (C) (D*)
Q.10 CH2 = C = O
)
equi
2
(
MgBr
CH
)
ii
(
Br
)
i
(
3
2


 
 C4H8O [2]
(A*) (B) (C) (D)Allofthese
Q.11
4
2
CCl
Br



Br
Br
|
|
COOH
CH
CH
HOOC 

 (X) [2]
4
2
CCl
Br



Br
Br
|
|
COOH
CH
CH
HOOC 

 (Y)
The correct statement with respect to above reactions are
(A*) The reactionis stereospecific
(B*) (X) is erythro and (Y) is threo isomer
(C) (X) is threo and (Y) is erythro isomer
(D) eachgives mixture of(X)and (Y)
Q.12 Which is B in the sequence 
 

HBr A
A
O
H
/
CO
)
ii
(
ether
/
Mg
)
i
(
3
2




 
 B [2]
(A) (B*) (C) (D)

4. Q.13 Givemechanismfor givenreaction: [4]


 


HOH
/
H
-Terpeniol
[Ans. 


H  

 


H
/
HOH ]
Q.14 Draw the structures ofstable configuration obtained after acidic hydration ofthe following unsaturated
compounds: (exclude rearranged products) [4]
(I) (II) (III) (IV)
[Ans. (I) (II) (III) (IV) ]
Q.15 Formulatemechanisms forthe following transformations. [4]


 
 2
2N
CH
[Sol.
]

5. ORGANICCHEMISTRY
Daily Practice Problems
CLASS : XIII (ALL) DPP. NO.-21
Q.1 Classicalcarbocationcontain:
(A) a lone pair (B) a vaccant orbital (C) three bond pairs (D*) B and C both
Q.2 


 
 4
2SO
H
.
Conc
A, Ais:
(A) (B*) (C) Both (D) None
Q.3 Which ofthefollowing is most acidic
(A) (B)
3
3 H
N
CH

 (C) (D*)
Q.4 The decreasingorder ofreactivitytowards electrophilic addition is:
(A) III > II > II > I (B) IV > I > II > III (C) II > III > I > IV (D*) II > III > IV > I
Q.5(a)
3
3
3
CH
|
OH
C
CH
|
CH


Heat
H



? (b)
3
Heat
H
3
3
CH
OH
)
Minor
(
)
Minor
(
)
Major
(
|
|
?
?
?
CH
CH
CH
CH 







(c)
)
Minor
(
)
Major
(
?
?
Heat
H




(d) 


 
 4
2SO
H
.
conc
(e)


 

,
HCl
AlCl3
C
Q.6 + HBr 
This involves 1,4addition ofHBr followedbyenolisationofketo group. Explain the mechanism.

6. Q.7 Arrange thefollowing inincreasing orderofstability.
(a) , , , , (regarding stabilityoffree radical)
(b)
2
2 H
C
CH

 ,
2
2 CH
CH
H
C 


, , (regarding to stabilityoffree radical)
Q.8 Supplythe structure &type ofintermediate species designated by
(a) + H+ 
 
 ? + H2O (b) CH3CH2 – N = N – CH2CH3

 
 ? + N2
(c) CH3CHI2 + Zn  ? + ZnI2 (d) CH3C  CH + NaNH2  ? N a

+ NH3
(e) CH3CH2Cl + AlCl3  AlCl4
– + ?
Q.9 Give major organic product in each case.

7. ORGANICCHEMISTRY
Daily Practice Problems
CLASS : XIII (ALL) DATE : 06/10/2006 DPP. NO.-22
Q.1 As manyas nine different Diels–Alder products can be obtained byheating a mixture of1,3-butadiene
and 2-methyl-1,3-butadiene. Identifythe products.
Q.2 Dr. HarryPottertreated1,3-cyclohexadienewithBr2 andobtainedtwo products(ignoringstereoisomers).
Her labpartner treated 1,3-cyclohexadiene withHBr and was surprised to find that onlyone product
was formed(ignoring stereoisomers).Account forthese results.
Q.3 How wouldthe following substitutents affect the rate ofaDiels–Alder reaction?
(a) anelectron-donating substituent inthe diene
(b) anelectron-donating substituent inthe dienophile
(c) anelectron-withdrawing substituentinthe diene
[Ans. (a) increases, (b) decreases, (c) decreases]
Q.4 Give two sets of a conjugated diene and a dienophile that could be used to prepare the following
compound.
Q.5 Whichofthe following conjugated diene would not react witha dienophile in aDiels–Alder reaction?
(a) (b) (c) (d)
(e) (f) [Ans. a, d]
Q.6 What diene and what dienophile shouldbe used to synthesize the following compounds?
(a) (b) (c) (d)
(e) (f)
Q.7
(a) How manylineardienes are there withmolecular formula C6H10? (Ignore cis–trans isomers)
(b) How manyofthese are conjugated dienes?
(c) How manyofthese are isolated dienes? [Ans. 6, 2, 2]

8. Q.8
(a) Which dienophileis more reactive ina Diels–Alder reaction?
(i) CHCH
CH
|
|
O
2  or CH
CHCH
CH
|
|
O
2
2 
(ii) CHCH
CH
|
|
O
2  or CH2=CHCH3
(b) Whichdiene is more reactive ina Diels–Alder reaction?
CH2=CHCH=CHOCH3 or CH2 = CHCH = CHCH2OCH3
[Ans.(a)(i) CHCH
CH
|
|
O
2  (ii) CHCH
CH
|
|
O
2  , (b) CH2=CHCH=CHOCH3]
Q.9
(a) Give allpossible products ofthefollowing reaction:
+ Br2 
(b) How manystereoisomers ofeach product could be obtained?
[Ans.
stereoisomers 2 2 4 ]
Q.10 The following equilibriumis driven to the right if the reaction is carried out in the presence ofmaleic
anhydride. What is the function ofmaleic anhydride?
+
[Ans. Maleic anhydridereact withcyclopentadiene and shift equilibriumtoward right]
Q.11 Give the product or products that would be obtained fromeach ofthe following reactions:
(a) + CH2= CH – CH = CH2 


(b) + 2
2
3
CH
C
CH
CH
|
CH


 


(c) + 3
2 CHCCH
CH
|
|
O
 



9. (d) + CH2 = CHCH2Cl 


Q.12 Explainwhythe following are not opticallyactive:
(a) The product obtainedfromthe reaction of1,3-butadiene withcis-1,2-dichloroethene.
(b) The product obtained fromthe reaction of1,3-butadiene withtrans-1,2-dichloroethene.
[Ans. (a) meso, (b) racemic]
Q.13 Write mechanismforfollowing reaction.
(a)
O
H
Br
2
2



(b) + 

(c)
4
2
CCl
Br



Q.14
(a) Give theproducts obtained fromthe reactionofone mole ofHBr with onemole of1,3,5-hexatriene.
(b) Whichproduct(s) willpredominate ifthe reactionis under kinetic control?
(c) Which product(s) willpredominate ifthe reactionis under thermodynamic control?
[Ans. 3 products, CH3–CH=CH–CH=CH–CH2–Br (TC)]
Q.15 How could the following compounds besynthesized using a Diels–Alder reaction?
(a) (b)
(c) (d)

10. ORGANICCHEMISTRY
Daily Practice Problems
CLASS : XIII (ALL) DATE : 09/10/2006 DPP. NO.-23
Q.1 How many litres ofmethane would be produced when0.6 gmof CH3MgBr is treated withexcess of
C4H9NH2
(A) 0.8 litre (B) 0.08 litre (C*) 0.112 litre (D) 1.12 litre
[Sol.  119 gmMeMgBr gives 22.4 lit
 0.6 gmwillgive 6
.
0
119
4
.
22
 = 0.112 lit. ]
Q.2 2CH3MgBr 



 

H
)
ii
(
ONH
CH
)
i
( 2
3
(A) CH3–O–NH–CH3 (B) CH3–NH–CH3
(C*) CH3–NH2 (D) CH3–O–CH3
[Sol. CH3MgBr + CH3ONH2  CH4 + CH3ONHMgCl
CH3OH + CH3–NH2 
 


O
H3 CH3NHMgCl + CH3OMgBr ]
Q.3 + MeMgCl 
 


O
H3
A 
 

HBr
B
O
Et
Mg
2


 C


 

O
H
HCHO
3
D
D is :
(A) (B) (C*) (D)
Q.4 5
2
5
2
H
OC
C
O
H
C
|
|
O

 


 

MgBr
CH
2 3 A. ProductAformed
(A) is ethylacetate
(B) furtherreact withCH3MgBr/H2O+ to give acetone
(C*) furtherreact withCH3MgBr/H2O+ to give t-butylalcohol
(D)A& B are correct
Q.5 Br–CH2–CC–CH2–Br
O
Et
)
excess
(
Mg
2


 BrMg–CH2–CC–CH2–MgBr
Product
The majorproduct is:
(A) Br–Mg–CH2–CC–CH2–Br (B) Cyclobutyne
(C) —
)
CH
C
C
CH
(
— n
2
2 

 (D*) CH2 = C=C=CH2
Q.6 The number ofmoles ofgrignardreagent consumed per moleofthe compound
is:

11. (A*) 4 (B) 2 (C) 3 (D) 1
Q.7
Me
|
Me
)
I
(
C
)
OH
(
C
Ph 3
AgNO
2



 


 ?
Major product is
(A)
Me
|
Me
)
NO
(
C
)
OH
(
C
Ph 2
3
 (B)
Me
|
Me
)
NO
(
C
C
Ph
|
OAg
2
3

(C) 3
CMe
CO
Ph  (D*) Ph C (Me2) C O Me
Q.8 



 

.)
eq
1
(
MgBr
CH3 ?
Theproduct is:
(A) (B) (C) (D*)
Q.9 Whichofthe following reacts withgrignard reagent?
(A)Acinitro formofCH3NO2 (B) enolformofacetylacetone
(C) Methane (D) Both(A) & (B)
Q.10
O
|
|
Cl
CH
CH
CCH
CH 2
2
2
3



 
 MgBr
CH3 A, Ais
(A)
OH
|
Cl
CH
CH
CCH
CH
|
CH
2
2
2
3
3
(B)
O
|
|
CH
CH
CH
CCH
CH 3
2
2
2
3
(C*) (D)
Q.11 3
2
2
2
3 CH
COCH
CH
CCH
CH
|
|
|
|
O
O







 

O
H
)
ii
(
)
mol
one
(
MgBr
CH
)
i
(
3
3 A,Aformed in this reaction is
(A)
3
3
2
2
2
3
CH
|
CH
COCH
CH
CCH
CH
|
|
|
O
OH
(B) 3
2
2
3 CCH
CH
CCH
CH
|
|
|
|
O
O

12. (C*) (D)
OH
OH
|
|
CCH
CH
CCH
CH
|
|
CH
CH
3
2
2
3
3
3
Q.12 CH3MgBr + CH2=CH 
C
|
|
O
H 
 


O
H3 Product (1 : 4 addition). It is
(A)
3
2
CH
|
H
C
CH
CH
|
OH


 (B)
OH
|
CH
CH
CH
CH 3
2 

(C*) CH3CH2CH2CHO (D) none
Q.13
O
OH
|
|
|
O
H
.
3
CH
CHCH
CH
.
2
ether
/
Mg
.
1
3
2
3







 
 Product (s)
Select the product fromthe following
I : II :
O
OH
|
|
|
CH
CHCH
CH 2
3 III :
(A) III (B) I, III (C*) I, II (D) II, III
Q.14 On conversion into grignard followed by treatment with ethanol, how manyalkyl halides (excluding
stereoisomers) would yield 2-methylbutane.
(A) 2 (B) 3 (C*) 4 (D) 5
Q.15 Propose mechanismforfollowing conversion.
O
H
)
ii
(
MgBr
CH
)
i
(
2
3



 

Q.16 (A) + xCH3MgBr  xCH4
C4H10O4
an alcohol(A) 20 gmwhen reacts withRMgx14.6lofCH4 willformedat STP?Find value ofx&give
structureformula.
Q.17 Two different grignard reagents (X) and (Y) produce
PhCH2C(CH3)2OH onreaction with Pand Q respectively. Give structure ofX, Y, Pand Q.
Q.18 Identify(A) to (B) :

13. Q.19 Additionofphenylmagnesiumbromide to 4-tert-butylcyclohexanonegives twoisomeric tertiaryalcohol
as product. Bothalcoholyield same alkene when subjected to acid-catalyzed dehydration. Suggest a
reasonable structure forthese two alcohol.
4-tert-butylcyclohexanone
Q.20 Neither ofthese methods of making pentan-1,4 diol will work. Explain why not – what will happen
instead?
(i) CHO–CH2–CH2–CH2–OH



 

H
by
followed
MeMgBr
OH
OH
|
|
CH
CH
CH
CH
CH 2
2
2
3 



(ii) Br–CH2–CH2–CH2–OH
O
Et
Mg
2


 MgBr–CH2–CH2–CH2–OH 


 

H
by
followed
CHO
CH3
OH
OH
|
|
CH
CH
CH
CH
CH 2
2
2
3 




14. ORGANICCHEMISTRY
Daily Practice Problems
CLASS : XIII (ALL) DPP. NO.-24
OBJECTIVE
Q1. What is the correct order of nitration ofthe following compounds?
C6H5CH3 C6H6 C6D6 C6T6 C6H5Br C6H5 N

R3 C6H5NMe2
a b c d e f g
(A) g > a > b > c > d > e > f (B) g > b > c > d > e > a > f
(C*) g > a > b = c = d > e > f (D) g > a > b > c = d > e > f
Q2. What is the correct order of o/p ratio when E+ attacks the following system?
PhF PhCl PhBr PhI
a b c d
(A*) a < b < c < d (B) a = b = c = d (C) d < c < b < a (D) d < b < a < c
Q3. Types of reaction o/p ratio
Chlorination x
Nitration y
Bromination z
sulfonation w
which of the following order is correct regarding o/p ratio?
(A) x > y > w> z (B*) x > y > z > w (C) y > x > z > w (D) x > z > y > w
Q4. What is the correct order of EAS of the following species?
N
a b c d e
(A) e > c > d > b > a (B) e > b > c > d > a
(C*) b > e > c > d > a (D) b = e > c > d = a
Q5. What is the order of reactivity offollowing hetero cyclic compound towards electrophile ?
I II III
(A) I > II > III (B) III > II > I (C) I > III > II (D*) III > I > II
Q6. Which of the following ions/ groups are o–p directing ?
(A) –CO2
– (B) –CH = CH – C HO (C) –CMe3 (D*)All
Q7. + PhCH = AlCl3
 

 Product (85%). Product is
(A) (B) (C*) (D) None

15. Q8. In which of the following reaction tertiary butyl benzene is formed ?
(A) + Me3C–OH + BF3 (B) + Me2C = CH2 + H2SO4
(C) + Me2CH – CH2Cl + AlCl3(hot)  (D*)All
Q9. + + H2SO4  Product
Product is
(A*) Phenolphthalein indicator (B) Fluoroscein dye
(C) Methylorange indicator (D) Butter yellow dye
Q10. What is the crrect order of EAS ofthe following compounds?
(a) (b) (c) (d)
(A*) c > d > b > a (B) d > b > c > a (C) a > b > d > c (D) none
SUBJECTIVE
Q.1 
 

NBS A 
 

KCN B 

 

HCl
,
O
H2 C 


 
 3
2 AlCl
,
SOCl D 


 

HCl
),
Hg
(
Zn E 
 

C
Pd F
What are Ato F ?
Q.2 CH3CO2H 
 
 4
AlPO B 

A C
3
AlCl
benzene
trimethyl
5
,
3
,
1






 
 CH3CO2H + D 




 

 HCl
.
conc
)
Hg
(
Zn E
What are B to E ?
Q.3 A(C7H6O)(gives+vetestwithtollensreagent) 
 
KCN
B(C14H12O2)
HCl
.
conc
)
Hg
(
Zn



 
 C(whichdecolorisesBr2 water)
dil. HNO3
D (C14H10O2) 



 


H
.
2
,
KOH
.
1 E (C14H12O3)
What areAto E?
Q.4
2
2
ZnCl
O
CH
HCl



 
 A 
 

KCN
B 
 


O
H3
C 
 
 2
SOCl
D
3
AlCl
PhH

 
 E
What areAto E?
Q.5 PhCH=CH–CH3 + Br2 (Fe)  A
peroxide
HBr

 
 B

16. Q.6 A
bromide
propyl
n
NaNH2


 
 B
H2 + Lindlar’s Catalyst
HBr
D
C
E
1,1 diphenyl ethane
+H+ +
HBr + Peroxide
What areAto E?
Q.7 A(C13H10NOBr) 

 

HCl
.
conc B(C7H6O2) + C 


 

HCl
NaNO2 D 


 

bromide
)
I
(
Cu E 



 

 4
2
3 SO
H
HNO F
Displace CO2 only
from Na2CO3 solution one pdt.
Q.8 Conversion : 
Q.9 Conversion : 
Q.10 Conversion :  1-phenylnapthalene
Q.11 Phenol is converted into nitrophenolin presence of mixture of HNO2 & HNO3. Here HNO3 having
dual purpose. Explainwithmechanism.
Q.12 When 1 methoxy 2 phenyl ethane is nitrated with nitrating mixture (HNO3 & H2SO4), p isomer is
formed as major product whereas with N2O5 results information of69% o &28% p-isomer. Explain.

17. ORGANICCHEMISTRY
Daily Practice Problems
CLASS : XIII (ALL) DATE : 13/01/2007 DPP. NO.-25
OBJECTIVE
Q1. +NaNO2 + HCl 
This reactionis example of
(A) IntermolecularC–N coupling (B) IntramolecularC–N coupling
(C) Intermolecular N–N coupling (D*) IntramolecularN–N coupling
Q2. For chlorinationofbenzene whichofthe following reagent should be used?
(A) BrCl (B) ICl (C*) HOCl + H+ (D)All
Q3. Whichofthefollowing statement is not correct regarding desulfonation?
(A)Allsteps are reversible (B) it exhibitskinetic isotope effect
(C) Phenol when reacts with SO3 at low temperature o–product is formed & at high temperature
p–product is formed as mojor product.
(D*) none
Q4. A(C9H12) KMnO4
 
 B(C8H6O4)
Br
Fe
2
 
 C(C8H5BrO4) (product only). Ais
(A) (B) (C*) (D)
Q5. What is the correct order ofEAS ofthe following compounds ?
PhCH3 PhCH2CO2Et PhCH(CO2Et)2 PhC(CO2Et)3
I II III IV
(A*) I > II > III > IV (B) IV > III > II > I (C) I = II = III = IV (D) none
Q6. What is the order ofEAS ofthe following compounds?
Terephthalic acid Toluene pToluic acid p Xylene
I II III IV
(A) II > III > I > IV (B) I > III > II > IV (C) IV > I > II > III (D*) IV > II > III > I
Q7. What is the order ofEAS ofthe following compounds?
Mesitylene mXylene p Xylene Toluene
I II III IV
PhCH2 N

Me3 PhCH2CH2 N

Me3 PhN

Me3
V VI VII
(A) I > III > II > IV > V > VI > VII (B) I > II > III > IV > VI > V > VII
(C*) I > II > III > IV > V > VI > VII (D) none
Q8.
1
2 3
.
.
PhNMeCHO
POCl
 

 P. P is
(A) (B) (C*) (D)

18. Q9. + + H+  P is
(A*) (B) (C) (D) none
Q10. Compound A (C7H8O) is insoluble in water, dilute HCl & aqueous NaHCO3, it dissolves in dilute
NaOH. When Ais treated with Br2 water it is converted into a compound C7H5OBr3 rapidly. The
structure ofAis
(A) (B) (C*) (D)
SUBJECTIVE
Q1. (i) + Me3C – COCl + AlCl3  Product
(ii) + CH2Cl2 + AlCl3 (excess) Product
Q2. The action of Me3C–CH2Cl /GaCl3 on benzene is found to yield 100% PhCMe2CH2Me whereas in
presence of FeCl3 product is 100% PhCH2CMe3 . Explain.
Q3. Aromatic bromination catalysed bylewis acid thalliumacetatel(CH3CO2)3 gives onlypara-isomer.
Explain.
Q4. Give a mechanismfor DDT preparationfromchlorobenzene & chloralinpresence ofH2SO4.
Q5. When aniline is subjected to FridelCraftAlkylation inpresence ofcatalytic amount ofAlCl3 alkylation
does not occur while in presenceofexcessAlCl3 smallamount ofmeta product is formed.
Q6. Phenol reacts with Br2 water to form2, 4, 6 tribromophenol but inpresence ofBr2 in CS2 mediumit
formeither o- bromo phenolor p- bromo phenol. Give mechanism.
Q7.
SO
C
3
0
80
 
 1600
3
C
SO
 


Explaininterms ofstabilityofthe product with energyprofile.
Q8. Phenyl triphenylmethylether whenontreatment withacid gives p-triphenylmethylphenol. Explain.
Q9. m-t-butylphenolreacts with Cl2 to give trichloro derivative, withbromine gives dibromo derivative, &
withI2 to givemonoiodo derivative. Explain.
Q10. Accountsforthe following facts
(i) N, N dimethylaniline reacts withHNO2 &so does thecorresponding 2, 6 dimethylderivativebut the
rate ofreactionoflatter is muchless w.r.t. former.
(ii) PhN

2 Cl– couples with PhNMe2 but not with 2, 6 Me2 C6H3NMe2.

19. ORGANICCHEMISTRY
Daily Practice Problems
Q.1 Consider the reaction
+ 
 


OH
X
here X is
(A*) (B) (C) (D) None
Q.2 Indicate the correct choice among the following.
(A) N, N, 2, 6-tetramethylaniline is less basic thanN, N–dimethylaniline
(B) C6H5 – NH – C6H5 reacts with nitrous acid to give
(C) Ph – O – CPh3 to
rearranges
H


 


(major product)
(D*) N, N-dimethylpicramide is a stronger base than picramide
Q.3 Inthegivenreaction:
OH
H
C
ONa
H
C
5
2
5
2


 
 (P)
(P) is:
(A*) (B) (C) (D)
Q.4 Which one ofthe following compounds is most reactive forArSN2 reaction?
(A) (B) (C*) (D)
CLASS : XIII (ALL) DPP. NO.-26

20. Q.5 Inthegivenreaction.
I
CH
)
ii
(
/
KOH
)
i
(
3




 
 (P)
(A) (B) (C*) (D)
Q.6 Which one ofthe following arylamines undergoes diazotisationmost readily?
(A) NO2 NH2 (B) Cl NH2
(C*) CH3O NH2 (D) CH3 NH2
Q.7 Inthegivenreaction:

 
 3
HNO
(A) 

 


H
/
O
H2 (B) 




 

HCl
.
conc
/
NaNO2 (C) 

 
 2
3PO
H
(D)
(D)is:
(A*) (B)
(C) (D)
Q.8 The finalproduct ofthe givenreaction sequence


 

S
)
NH
( 2
4
C
5
0
HCl
NaNO2




 

2
3
2
2
)
NO
(
Cu
O
Cu
,
O
H



 

is:
(A) (B*) (C) (D)

21. Q.9 Inthegivenreaction:
(P)
(P) willbe
(A) (B)
(C*) mixture of(A) and (B) (D)
Q.10 CompoundA& B both having molecular weight 104.
A 


C C &D having molecular weight 172.
B 


D C shows geometricalisomerismbut D cannot. What is the structure ofAto D?
Q.11 (Subsitutedelectrophilic aromatic) S.E.Ar inmost favourable at position
Q.12 Complete thefollowing equations
(a) Resorcinol + MeCO2H 

 
 4
3PO
H
(b) 
 

 ICl
2
(c) + A 



H
Q.13 Whichoffollowing is in-capable to show Iodoformtest
(A) (B) 3
CH
CH
CH
CH
Ph
|
OH




(C*) (D)

22. Q.14 H
C
CH
CH
CH
||
|
O
OH
2
3 



aldol)
(Retro
HO

 


(A)
3HCHO + A
C
40
CO
Na 3
2



 
 %)
82
(
)
B
(
Product (B) ofabove reaction is
(A)
OH
CH
|
OH
CH
C
CH
HO
|
OH
CH
2
2
2
2





(B)
OH
CH
|
CHO
C
CH
HO
|
CHO
2
2




(C*)
CHO
|
OH
CH
C
CH
HO
|
OH
CH
2
2
2


 (D)
OH
CH
|
OH
CH
CH
C
CH
HO
|
CHO
2
2
2
2






Q.15 Arrange the followingcarbonylcompounds indecreasingorder oftheirreactivityinnucleophilic addition
reaction.
(A) b > c > a > d (B*) b > a > d > c (C) c > b > a > d (D) c > a > d > b
Q.16 Identify(X) ofthefollowingreaction:



 

acid
s
'
Caro (X)
(A*) (B)
(C) (D)
Q.17 Identifytheproduct obtained inthefollowing reaction:
C
0
/
CHCl
Br
3
2



 (A)

23. (A) (B)
(C*) (D)
Q.18 Inthegivenreaction:
Cl
C
Cl
|
|
O

 + 2C6H– 
 
 2
ZnCl
(X)
(A) C
Cl
|
|
O
 (B)
(C) C
CH
|
|
O
3  (D)
Q.19 Finalproduct ofthe givenreaction:
Fe
Br2


 (A) 

 

ether
/
Mg
(B) (C)
(C) is:
(A) (B) (C) (D)
Q.20 The compound that gives a lactoneonheating is
(A) pentaedioic acid (B*) 4-hydroxypentanoic acid
(C) 4-aminopentanoic acid (D) 2-hydroxypentanoic acid
Q.21 Point outthewrongformulation.
(A) C6H5 – Br + (CH3– CO)2 O 
 
 3
AlCl
(B) + CH3 – COCl 
 
 3
AlCl

24. (C*) + CH3 – COCl 
 
 3
AlCl
(D) C6H5 – NO2 + EtCl 
 
 3
AlCl
no reaction

25. ORGANICCHEMISTRY
Daily Practice Problems
Q.1 Give structureand names oftheprincipalorganic products expected frommononitrationof
(a) o-nitrotoluene (b) m-dibromobenzene
(c) m-dinitrobenzene (d) o-cresol
(e) p-cresol (f) m-nitrotoluene
(g) p-xylene (p-C6H4(CH3)2) (h) terephthalic acid (p-C6H4(COOH)2)
(i) aniliniumhydrogensulfate (C6H5NH3
+ HSO4
—)
(j) m-cresol(m-CH3C6H4OH)
(k) p-nitroacetanilide (p-O2NC6H4NHCOCH3)
Q.2 For eachofthe following compounds, indicate whichring youwould expect to beattacked in nitration,
and give structuresofthe principalproduct
Q.3 Conversion:
(i) toAniline (ii) CH2 = CH–CH = CH2 
Q.4 An aromatic compound having the molecular formula C13H9OCl A reacts with hydroxylamine
hydrochloride forming acompound B.AdryetherealsolutionofB ontreatment withPCl5 at 0° forms a
compound C, whichmaybe hydrolysed to equalmolar quantities ofbenzoic acid and p-chloro-aniline.
What structure wouldyou assign toA? Explainthe reactions involved.
Q.5 IdentifyA– H.
A



 


O
H
,
H 2
B 
 

—
HO
C
C5H8O3
D



 


O
H
,
H 2
E




 

H
)
ii
(
excess
I
)
i
(
excess
HO
2
—
F 
 
 2
SOCl
G 

 

OH
CH3
H .
H ismethylpropionate.
[Sol. 3
2
3 COCH
CCH
CH
|
|
|
|
O
O



 


O
H
,
H 2
3
3CCH
CH
|
|
O

 


HO
3
3
2
3
CH
|
CCH
CCH
CH
|
|
|
O
OH
(A) (B) (C)
C5H8O3
CLASS : XIII (ALL) DATE : 15/01/2007 DPP. NO.-27

26. 3
3
3
CH
|
CCHCOCH
CH
|
|
|
|
O
O



 


O
H
,
H 2
3
2
3 CH
CCH
CH
|
|
O
excess
I
excess
HO
2



 


COH
CH
CH
|
|
O
2
3 
 
 2
SOCl CCl
CH
CH
|
|
O
2
3
(D) (E) (F) (G)
3
2
3 COCH
CH
CH
|
|
O
(H) ]
Q.6 



 

 3
2 HNO
HNO
A
DMF
SOCl2

 
 B
O
H
KOH
2

 
 C 

 

O
H
/
Br 2
2
D 

 

HCl
/
Sn
E
G
O
H
/
NaOH
)
iii
(
MeI
)
ii
(
,
NaH
)
i
(
2




 
 F
'G'is used for the preparation of"Antileukemiadrug" 'G' is
(A) G = (B) G =
(C*) G = (D) G =
Q.7 Thecorrect pKa a order offollowing compoundsin aqueous solution.

4
NH Me
H
N 3

2
2Me
H
N

3
HMe
N

(I) (II) (III) (IV)
(A) I < II < III < IV (B) III > II > I > IV (C*) III > II > IV > I (D) II > IV > III > I

27. Q.8 Inthegivenreaction
C6H5 – NH2 Pyridine
O
Ac2

 
 X 

 2
Cl
Y 
 

O
H2
Z
the product (Z) willbe:
(A)o-chloroaniline (B) 2,4-dichloroaniline
(C) 2, 4, 6-trichloroaniline (D*) mixture ofo and p-chloroaniline
Q.9 Arrange the following compoundsin order of decreasing reactivity towardselectrophilic aromatic
substitution reactionsand select thecorrect answer from thecodes.
(I) m-chloroanisole (II) p-chloroanisole (III) anisole (IV) N-methylaniline
Codes:
(A*) IV > III > I > II (B) IV > I > III > II (C) IV > II > III > I (D) IV > III > II > I
Q.10 In whichcompoundaromatic electrophilic substitutiontakes place at ortho and/ or para position?
(A) C6H5 – B(OH)2 (B) C6H5 – 2
3)
CH
(
N

(C*) C6H5 – C6H5 (D) C6H5 – NO2
Q.11 Inthegivenreaction:
C6H6 + X 

 
 4
2SO
H C6H5
(X)is:
(A) (B) OH (C*) Both(A) and (B) (D) Cl
Q.12 Inthegivenreaction:
A + B




 
 3
AlCl
Anhy
(A) and CH3 (B) and
(C) and (D*) Both(A) and (B)
Q.13 Give structuresand names oftheprincipalproducts expected fromthe ring monobrominationofeachof
the following compounds. In each case, tellwhether bromination willoccur faster or slower than with
benzeneitself.
(a) acetanilide (C6H5NHCOCH3) (b) iodobenzene
(c) sec-butylbenzene (d) N-methylaniline (C6H5NHCH3)
(e) ethylbenzoate (C6H5COOC2H5) (f) acetophenone (C6H5COCH3)
(g) ethylphenylether (C6H5OC2H5) (h) diphenylmethane (C6H5CH2C6H5)
(i) benzonitrile (C6H5CN) (j) benzotrifluoride (C6H5CF3)
(k) biphenyl (C6H5–C6H5)

28. Q.14 Arrange the compounds ofeach set inorder ofreactivitytowards electrophilic substitution. Indicate in
eachset whichwould yield the highest percentage ofmeta isomer, and which wouldyield the lowest.
(a) C6H5N(CH3)3
+, C6H5CH2N(CH3)3
+, C6H5CH2CH2N(CH3)3
+, C6H5CH2CH2CH2N(CH3)3
+,
(b) C6H5NO2 , C6H5CH2NO2 , C6H5CH2CH2NO2
(c) C6H5CH3 , C6H5CH2COOC2H5 , C6H5CH(COOC2H5)2 , C6H5C(COOC2H5)3
Q.15 3 methylphenol+ A(C10H13O2Cl) 
 


OH B (C10H12O2).
B 


 
 2
2CHNH
Me
C (C13
H21
NO2
) Toliprolol. What areAto C ?
Q.16 Explain the following changes and deducethe nature ofcompoundsAto F.
Q.17 Complete thereaction:
(i) RMgBr + 2
*
O
C  A 


H
B
2
2
2
N
CH
SOCl

 
 C 
 

O
Ag2
D 
 

O
H2
E
(ii) PhCH=NR 
 

MeI
?
O
H
H
2



A+ B
(iii) R2C(OH) CH2CR2NH2 
 
 2
HNO A+ B
(A) give positive Iodoformtest when R = – CH3

29. ORGANICCHEMISTRY
Daily Practice Problems
Q.1 Conversion : 
Q.2 Conversion : 
Q.3 Conversion :
O
OH
|
|
|
Ph
C
CH
Ph 

 




 

NaOH
.
2
,
NaBrO
.
1 3
Q.4 


?
Q.5 An aromatic compoundA(C6H5O2N) by clemmenson reduction produces B (C6H7N) which reacts
with sodium nitrite in presence of mineral acid to give C. Compound C when treated with
hypophosphorous acid gives D and this reacts with equimolar amount ofbromine in presence ofiron
catalyst to give E (C6H5Br). Reaction ofacetic anhydride on compound B produces F. Compounds E
and Fwhenrefluxed withpotassiumcarbonateinan inert solvent inpresence ofcopperpowder givesG
(C12H11N). IdentifyA, B, C, D, E, F and G. Give reactions.
Q.6 CompoundA(C7H12O4) is an ester of a dicarboxylic acid and undergoes hydrolysis to give a product
whichgivespositive iodoformtest. CompoundB (C7H6O) givesoxime andhydrazone whenreactswith
hydroxylamineandhydrazine respectively, andit is synthesized bypassing amixtureofcarbonmonoxide
and hydrogen chloride in benzene in presence of catalysts. Aand B gives a condensation reaction in
presence of a base, Pyridine to give a compound C of formula (C14H16O4) which on hydrolysis and
subsequent heating produces cinnamic acid. Give structuresofA, B and C. Give reactions.
Q.7 A naturally occurring compound C10H12O2 (A) is soluble in aqueous NaOH but not in NaHCO3.
Treatment of (A) (i) with methyl sulphate and aqueous NaOH gives compound (B) (C11H14O2) ;
(ii) withhot concentratedbase gives compound (C) C10H12O2. Compound (B) is insoluble in aqueous
NaOH and readilydecolourises dilute KMnO4 and Br2/CCl4. Treatment of(B) with hot concentrated
base gives (D) C11H14O2. Ozonolysisof(C) givesa compound that is isomeric withvanillin. Ozonolysis
of(D) gives a compound that identicalwiththe one obtained fromthe treatment ofvanillinwithmethyl
sulphate. What are structures of (A), (B), (C) and (D) ?
Q.8 AcompoundA(C13H11NO) onhydrolysis producesB (C7H6O2) andC (C6H7N). Compound B when
heatedwithsodalimeproducesbenzene, whilecompoundConheatingwithchloroformandalkaliproduces
phenylisocyanideofcharacteristicbad odour. CompoundAisformedbytreating theetherealsolutionof
compound D (C13H11ON) withphosphorous pentachloride. IdentifyA, B, C and D. Give reactions.
Q.9 A compound A (C9H10O) on treatment with NaOH and iodine gave iodoform and a compound B
(C8H8O2) which on treatment with SOCl2 and then with NH3 gave a compound C (C8H9NO). The
compound C was treated with NaOH and Br2 to give a compound D (C7H9N) whichwas first treated
with cold dil. HCl and NaNO2 and then with a solution of KI to give p-iodotoluene. What are the
structures ofA, B, C and D?
CLASS : XIII (ALL) DPP. NO.-28

30. Q.10 On treatment with bromine, certain diarylmethanols (I) are converted into a 50 : 50 mixture of aryl
bromide (II) and aldehyde (III)
+ Br2  +
(I) (II) (III)
Whether G is –NO2, –H, –Br, or –CH3, bromine appears onlyin the ringcontaining the –OCH3 group.
The rate ofreaction is affected moderatelybythe nature ofG, decreasing along the series :
G = – CH3 > –H > –Br > – NO2.
Outline allsteps inthe most likelymechanismfor thisreaction. Show how yourmechanismaccounts for
each ofthe above facts.

31. ORGANICCHEMISTRY
Daily Practice Problems
Q.1 End products ofthe following sequenceofreaction is

 

NBS


 

ether
/
Mg



 

O
H
CN
CH
3
3
(A) (B) (C) (D)
Q.2 1-octene 
 

NBS ?
Major product inthe above reaction is
(A*) 3-bromo-1-octene (B) 2-bromo octane
(C) 1-bromo octane (D) 1-bromo-2-octene
Q.3
B
A
HI
.
conc
HI
.
anhy


 



 

A &B are respectively:
(A) & (B) &
(C) Both (D*) Both
Q.4



OH
Olefinic product.
Identifymajor product
(A*) (B) (C) (D) None ofthese
Q.5 + HCO2Et 
 

EtONa
(X)
Identify unknown (X) in above reaction
(A) (B) (C*) (D)
CLASS : XIII (ALL) DPP. NO.-29

32. Q.6 Guess the product
CH3CH2CONH2


 
 5
PCl
?
(A*) CH3CH2–CN (B) CH3CH2COCl (C) CH3CCl2CONH2 (D) CH3CH2CONHCl
Q.7 Correct orderofyield ofHofmannalkene in following reactionwillbe
X
|
CHCH
CH
CH 3
2
3 X may be F, Cl, Br or I
(A*) F > Cl > Br > I (B) I > Be > Cl > F
(C) Cl > F > Br > I (D) I > Br > F > Cl
Q.8


 


OH
(A)




 

,
OH
)
ii
(
X
CH
)
i
( 3 (B)




 

,
OH
)
ii
(
X
CH
)
i
( 3
(C).
Identify(C)
(A) (B) (C*) (D)
Q.9 
 

EtOH products. Expected products are:
(I) (II) (III)
Select correct alternates
(A) I, II & III (B) I, III (C*) II, III (D) I, II
Q.10 

 

COCl
CH3 


 

COOK
CH3
A 


B
(A) (B*) (C) (D) None of these
Q.1 Ei


Whichofthe following product cannot be obtained bythis reaction.
(A) (B) (C) (D*)

33. ORGANICCHEMISTRY
Daily Practice Problems
Q.1 Compare the two methods shownfor the preparationofcarboxylic acids:
Method 1: RBr
ether
diethyl
Mg

 
 RMgBr



 

O
H
)
ii
(
CO
)
i
(
3
2 RCO2H
Method 2 : RBr 
 

NaCN
RCN
heat
HCl
,
O
H2


 
 RCO2H
Whichofthe following statements correctlydescribes this conversion?

(A) Bothmethod 1 and method 2 are appropriate for carrying out this conversion.
(B) Neither method1 nor method 2is appropriate for carrying out this conversion.
(C*) Method 1 willwork well, but method 2 is not appropriate.
(D) Method 2 willwork well, but method 1 is not appropriate.
Q.2 The finalproduct Z inthefollowing reactionis:
4
CCl
NBS

 
 [ ] 


 

COK
)
CH
( 3
3 [ ] Z
(A) (B) (C*) (D)
Q.3 What are themost likelyproducts ofthe reactionshown below?

 


O
H3
(A) & (B*) &
(C) & (D) &
Q.4 Identifytheproduct (Y) inthefollowing reactionsequence:
+ 


 

O
H
)
ii
(
AlCl
)
i
(
3
3
(X) 


 


H
/
)
Hg
(
Zn
(Y) 

 
 4
3PO
H
(A*) (B)
(C) (D)
CLASS : XIII (ALL) DPP. NO.-30

34. Q.5 Identifythefinalproduct.
PhCH3
4
2
3
SO
H
HNO

 
 P–O2N–C6H4CH3 


 

H
MnO4
(X)
3
2
NH
)
ii
(
SOCl
)
i
(


 
 (Y) 
 
 5
2O
P
(Z)
(A) P–O2N–C6H4–CO2H (B*) P–O2N–C6H4–CN
(C) P–O2N–C6H4–CONH2 (D) P–O2N–C6H4–CH2CN
Q.6 The halogencompound most likelyto undergo nucleophilic substitutionisinwhichcompound
(A) (B) (C) (D*)
Q.7 'A'is ahigher phenoland 'B'is an aromatic carboxylicacid. Separationofamixture of'A'and 'B' can be
carried out easilybyhaving a solution of
(A) NaOH (B) Na/ether (C) Lime (D*) NaHCO3
Q.8
Fe
Br2


 substitution takeplace at the position.
(A) 1 (B) 2 (C*) 3 (D) both(A) & (B)
Q.9 + Cl
C
CH
|
|
O
3 
 A
3
2 FeCl
,
Cl

 
 B



 

OH
)
ii
(
HCl
.
aq
)
i
(
C
Product 'C' is
(A) (B*) (C) (D)
Q.10
A




 


O
H
)
ii
(
H
O
I
)
i
(
3
—
2
B 



 

 O
H
Br
excess 2
2 C
'C' formwhite precipitate compound 'C' is:
(A) (B) (C*) (D)

35. Q.11
excess
NaOH

 
 A.Ais:
(A) (B*) (C) (D)
Q.12 Arrange these compounds inorder ofincreasing SN2 reaction rate:
(A) III < I < II < IV (B) III < II < I < IV (C*) IV < III < I < II (D) III <IV < I < II
Q.13 2-bromopentane onreactionwithalcoholic KOH give(s)
(A) Pent-1-ene
(B) cis and trans pent-2-ene but trans is in major yield
(C) cis and trans pent-2-ene but cis isomer is inmajor yield
(D*) pent-1-ene, cis pent-2-ene and trans-pent-2-ene but trans pent-2-ene is in major yield
Q.14 Match List-I with List-II(no. ofproducts in-elimination) andselect the correct answer.
List-I List-II
(a) (i) Three
(b) (ii) Zero
(c) (iii) One
(d) (iv) Two
(a) (b) (c) (d) (a) (b) (c) (d)
(A) (i) (ii)(iv) (iii) (B*) (iv) (iii)(i) (ii)
(C) (iv) (iii)(ii) (i) (D) (i) (iii)(iv) (ii)
Q.15 (A) C9H10 O2 
 


O
H3 (B) + (C)
(positive lodoform) (1, 4-dihydroxybenzene)
[Ans. (A) , (B) = 3
3 CH
C
CH
|
|
O

 ]