1. Illustration 1: Which one of the following does not of dissolve in conc. H2SO4?
(A) CH3 – C = C – CH3 (B) CH3 – CH2 – C  CH
(C) CH  CH (D) CH2 = CH2
Solution: If CH  CH were to dissolve in H2SO4 a bisulphite salt of vinyl carbocation
H2C = C+
H would be formed. The more s-character in the positively charged
‘C’ less stable is the carbocation and less likely to be formed.
(C)
Illustration 2: Which one of the following compounds will give in the presence of peroxide a
product different from that obtained in the absence of peroxide?
(A) 1-butane (B) 1-butene, HBr
(C) 2-butene, HCl (D) 2-butene, HBr
Solution: Peroixde effect is observed when unsymmetrical alkene is treated with HBr
only (and not with HCl and HI).
(B)
Illustration 3: Which of the following alkene on acid catalysed hydration form 2-methyl
propan-2-ol.
(A) (CH3)2CH = CH2 (B) CH3 – CH = CH2
(C) CH3 – CH = CH – CH3 (D) CH3 – CH2 – CH = CH2
Solution: Addition of H2O occurs according to Markownikoff’s rule.
CH3 – C = CH2 + H2O 



H
CH3 – C + CH3
CH3 CH3
CH3
 (A)
Illustration 4: Which of the following compounds yields only one product on
monobromination?
(A) Neopentane (B) Toluene
(C) Phenol (D) Aniline
Solution: CH3 –
|
CH
CH
|
C
3
3
 CH3 has twelve equivalent 1°H. Hence H forms only one product
on monobromination.
(A)

2. Illustration 5: Aqueous solution of the following compounds are electrolysed. Acetylene gas
is obtained from.
(A) Sodium fumarate (B) Sopdium maleate
(C) Sodium succinate (D) Both (A) and (B)
Solution:
+ 2CO2 + 2C at cathode
CH – COO–
||
CH – COO–
CH
|||
CH
 (D)
Illustration 6: Dehydration of butan-2-ol with conc. H2SO4 gives preferred product.
(A) but-1-ene (B) but-2-ene
(C) propene (D) ethane
Solution: CH3 – H
|
H
C –
|
OH
CH – CH3



 
 4
2SO
H
CH3 – CH = CH – CH3 (80%)
+ CH3 – CH2 – CH = CH2 (20%)
This is in accordance with saytzeff rule.
 (B)
Illustration 7: CH3 – C  C – CH3 

 
 2
NaNH
‘X’. What is X
(A) CH3CH2CH = CH2 (B) CH3CH2C  CH
(C) CH3 – CH = CH – CH3 (D) CH2 = C = CH – CH3
Solution: Isomerisation occurs, when 2-butyne is treated with NaNH2, it converts into
terminal alkyne (1-butyne).
 (B)
Illustration 8: Identify the compound ‘Y’ in the following sequence of reaction
HC  CH Y
X
COOH
CH
/
Zn
Zn
/
O
H
)
ii
O
)
i 3
2
3




 


 

(A)
O
H
OH
(B)
O
OH
(C) C
H3
OAc
OAc
(D) CH3COOH
Solution: C
H CH 


 
 duction
Re
O
O



 
Ozonolysis
O
H
OH
 (A)
Illustration 9: Dehydration of 1-butanol gives 2-butene as a major product, by which of the
following intermediate the compound 2-butene obtained

3. (A)
C
H3
CH2
+
(B)
C
C
H3
CH2
CH3
+
(C) CH
C
H3
CH3
+ (D)
+
C
H3 CH2
CH3
Solution:
Shift
hydride
2
,
1



 

C
H3 OH C
H3
CH2
+
C
H3
CH2
+





H
C
H3 CH
CH3
+
2° 1°
 (C)
Illustration 10: The principal organic compound formed in the reaction
CH2 = CH(CH2)8COOH + HBr 

 
Peroxide
…………. is
(A)
CH3 –
Br
|
CH– (CH2)8COOH
(B) CH2 = CH(CH2)8COBr
(C)
Br
|
CH2 –CH2(CH2)8COOH
(D)
CH2 = CH(CH2)7 –
Br
|
CH– COOH
Solution: Follows the peroxide effect
 CH2 = CH(CH2)8COOH
Peroxide
HBr

 

Br
|
CH2 – CH2(CH2)8COOH
 (C)
Illustration 11: Product)
(Major
nation
Monochlori




 

C
H3 CH3
CH3
(A)
Cl
CH3
CH3
(B) C
H3 CH3
Cl
CH3
(C)
C
H3 CH3
Cl
(D)
C
H3 CH3
CH3
Cl

4. Solution: Probability selectivity
 (B)
Illustration 12: The reactivity order of alkyl halides is 3°  2°  1° in
(A) Both SN1 and SN2 (B) both SN2 and E2
(C) Both E1 and SN2 (D) Both SN1 and E2
Solution: For SN1, E1 and E2 reactivity order is 3°  2°  1°
 (D)
Illustration 13: How many optically active isomers of monochloride can be obtained from 2-
methyl butane
(A) 1 (B) 2
(C) 3 (D) 4
Solution: Two chiral centre generates
 (B)
Illustration 14:
is
B
.
B
A
,
O
H
)
ii
excess
KCN
)
i
PCl
3
5






 


 

C
H3 CH3
O
(A) C
H3 CH3
Cl
CN
(B)
C
H3 CO2H
CH3
(C) C
H3 CH3
Cl
CO2H
(D) C
H3
CO2H
O
Solution:
C
H3
CH3
O

 
 5
PCl
CH3
Cl
C
H3
Cl
CH3
NC
C
H3
CN
CH3
HO2C
C
H3
CO2H
C
H3 CH3
CO2H
 (B)
Illustration 15: The following in order of leaving group capability
F–
(I), CF3SO3
=
(II), –
OH(III), I–
(IV)
(A) I  III  IV  II (B) III  I  IV  II
(C) II  III  IV  I (D) IV  III  I II
Solution: Weaker the base good is the leaving group
 (A)
Illustration 16:
is
F
,
F
HBr

 

C
H3
OH
(A)
C
H3
Br
OH (B)
C
H3
OH
Br
(C)
C
H3
Br (D)
C
H3
OH
Br
Br

5. Solution: Protonation occurs on doubled bon
 (B)
Illustration 17:
OH
Me
H
Ph
Pyridine
SOCl2


 

For the above reaction which of the following statement is not correct
(A) Rate = K[Alcohol] [SOCl2]
(B) In the product inversion of configuration also takes place
(C) This reaction is an example of SN2
(D) In the product retention of configuration takes place
Solution: Normal SN2 attack
(D)
Illustration 18:
is
Z
,
Z
NaI

 

H Br
H Br
Ph
Ph
(A)
Ph
H H
Ph
(B)
H I
H I
Ph
Ph
(C)
I H
H I
Ph
Ph
(D)
Ph
H Ph
H
Solution: Anti-dehalogenation takes place
 (A)
Illustration 19: When isopropyl alcohol vapours are passed over heated copper it gives
(A) Acetone (B) Ethyl alcohol
(C) Methyl alcohol (D) Acetaldehyde
Solution: (CH3)2CHOH
2
H
Cu


 
 CH3COCH3
 (A)
Illustration 20: Glycerol on treatment with oxalic acid at 110°C forms
(A) Formic acid (B) CO2 and CO
(C) Allyl alcohol (D) Glycol
Solution:
OH
|
CH2 –
OH
|
CH –
OH
|
CH2 + H2SO4  HCOOH + CO2 + glycerol

6. Illustration 21: CH3OH + PCl3  P, P is
(A) CH4 (B) CH3Cl
(C) CH3COCl (D) (CH3)2

Solution: (B)
Illustration 22: Dehydration of ethanol gives
(A) CH3COOH (B) C2H6
(C) C2H2 (D) C2H4
Solution: 

 
 

/
H
2
3 OH
CH
CH C2H4
 (D)
Illustration 23: The compound that will react most readily with NaOH to form methanol is
(A) (CH3)4N+
I–
(B) CH3OCH3
(C) (CH3)3S+
I–
(D) (CH3)3CCl
Solution: (CH3)4N+
I–

 


OH
(CH3)3 N + CH3OH
 (A)
Illustration 24:
OH
|
CH2 –
OH
|
CH2 + Pb(OAc)4  P?
(A) Oxalic acid (B) Glyoxal
(C) HCHO (D) Glycollic acid
Solution: (CH2OH)2 
 
 ]
O
[
2HCHO
 (C)
Illustration 25: Glycerol + Conc. H2SO4  ?
(A) Acrolein (B) Formic acid
(C) Allyl alcohol (D) CH3NC
Solution: CH2OH –
OH
|
CH – CH2OH 

 
 4
2SO
H
acrolein
2 CHO
CH
CH 

 (A)
Illustration 26: Mild oxidation of 2-propanol yields
(A) CH3COOH (B) CH3COCH3
(C) CH3CH2CHO (D) CH3CH2CH2OH
Solution: 3
3 CH
OH
|
CH
CH  
 
 ]
O
[
CH3COCH3
 (B)

7. Illustration 27: O
CH3
?
O
H
RMgX
2


 

(A)
CH3
R OH
(B)
CH3
O
H R
(C)
CH3
O
H OH
(D) None of these
Solution:


 
RMgX
CH3
R OH
O
CH3
 (A)
Illustration 28: A + Ca(OCl)Cl  CHCl3. A is
(A) C2H6 (B) C2H5OH
(C) C2H2 (D) CH3COOH
Solution: Molecule should contain 

O
||
C
CH3 or CH3 –
OH
|
CH – group to then haloform
reaction
 (B)
Illustration 29: O
CH3
O
C
H3
is
P
.
P
)
iii
H
)
ii
NaOBr
)
i




 

(A)
CH2
OH
O (B)
O
CH3
(C)
O
O
Br
(D) Br
CH3
Solution: Haloform reaction followed by acidification makes a -keto acid which on
heating decarboxy lates.
 (B)

8. Illustration 30:
is
X
,
X
H
O

 

C
H3 CHO
O
(A)
C
H3
OH
O
O
(B)
C
H3 COO
-
OH
(C)
O
H CHO
O
(D)
C
H3
OH
OH
Solution: Intramolecular cannzaro reaction.
 (B)
Illustration 31: A ketone reacted with C2H=5MgBr reagent followed by hydrolysis gave a
product which on dehydrationi gives an alkene. The alkene on oznolysis gave
diethyl ketone and acetaldehyde. The ketone is
(A) Dimethyl keton (B) Ethyl methyl ketone
(C) Diethyl ketone (D) Ethyl propyl ketone
Solution:
O
CH3
C
H3




 

O
H
)
ii
MgBr
H
C
)
i
3
5
2
OH
CH3
C
H3
CH3

 
 O
H2
CH3
CH3
C
H3
Zn
O
H
/
O 2
3


 
 O
CH3
C
H3
Illustration 32:
O
CH3
is the final product obtianed when which one of the
following is reacted with base?
(A)
C
H3 CH3
O
O
(B)
C
H3 CH3
O O

9. (C) C
H3
CH3
O
O
(D)
C
H3 CH3
O O
Solution: Intramolecular aldol condensation
 (B)
Illustration 33:
Ph
Ph
O
H
Ph
O
H
Me
H
+
A, A is
(A) Ph
Ph
Ph
O
Me
(B) Ph
Ph
Me
O
Me
(C)
Me
Ph Ph
Ph
(D)
C
H3
O
O
H
Ph
Ph
Solution: First stable carbocation is formed. Then pH group migrates.
 (A)
Illustration 34:
O
C
H3
H
is
B
.
B
X
CH
CH
)
iii
Li
Ph
)
ii
SH
CH
CH
C
H
)
i
2
3
2
2
2









 

(A) O
C
H3
C
H3
(B)
S
S
C
H3
C
H3
(C)
C
H3
OH
H
CH3
(D) S
S
Ph
C
H3
Solution:
S
S
H
C
H3
PhLi
S
S
CH3
CH3CH2X
S
S
C
H3
C
H3

10. Illustration 35: is
C
.
C
KOH
Methanolic



 

Cl
Ph
O
(A)
H3CO
Ph
O
(B)
C
H2 Ph
O
(C)
O
Ph
(D) Cl
CH3
OH
OMe
Solution: Caranian is formed adjacent to carbonyl group, then NGP takes place
 (C)
Illustration 36:
is
D
.
D
2
3
3 SeO
AlCl
COCl
CH

 



 

(A) CH3
O
(B) CHO
O
(C) CO2H
O
(D)
CH3
O
OH
Solution: F.C. acylation followed by oxidation. SeO2 Oxides – CH2 – group adjaenet (B)
top carbonyl group to 

O
||
C
 (B)
Illustration 37: Among the following which compound does not give iodoform test.
(A) C
H3 OH (B)
C
H3 CH3
O O
(C)
C
H3
CH3
OH
(D)
C
H3 OEt
O O
Solution: (D)
Illustration 38:

 
 H
O
CHO
C
H3
C
H3

11. (A) C
H3
CH3
CHO
CH3
OH
(B)
C
H3
CH3
CH3
C
H3
CHO
(C) COO
-
C
H3
C
H3
and
C
H3
C
H3 OH
(D)
C
H3
C
H3 O
O
C
H3
CH3
Solution: Cannizaro reaction takes place
 (C)
Illustration 39: On strong heating ammonium acetate gives
(A) methyl cyanide (B) acetamide
(C) urea (D) form amide
Solution: B
Illustration 40: The product (B) in the following reaction is
Acetamide 
 
 5
2O
P
A B
H
4



(A) CH3NH2 (B) C2H5NH2
(C) CH3CN (D) CH3COONH4
Solution: B
Illustration 41: Weakest acid among the following is
(A) CH3COOH (B) ClCH2COOH
(C) HCCl2COOH (D) Cl3C.COOH
Solution: A
Illustration 42: Formic acid and formaldehyde can be distinguished by treating with
(A) Benedict’s solution (B) Tollen’s reagent
(C) Fehling’s solution (D) NaHCO3
Solution: D
Illustration 43: The product (Y) in the following reaction is
C6H5CH2Cl B
A
2
3 )
NO
(
Cu
Oxidation
NaOH
Aq


 



 

(A) Benzoic acid (B) Phenol
(C) Toluene (D) Benzaldehyde
Solution: D

12. Illustration 44: (X) 
 
 2
Cl
Benzotrichloride )
Y
(
Hydrolysis



 

(X) and (Y) are respectively
(A) Benzene, benzaldehyde (B) Toluene, benzaldehyde
(C) Toluene, benzoic acid (D) Benzene, benzoic acid
Solution: C
Illustration 45: Aryl halides are less reactive towards nucleophilic substitution reaction as
compared to alkyl halides due to
(A) The formation of less stable carbonium ion
(B) Resonance stabilization
(C) Lower carbon-halogen bond
(D) Inductive effect
Solution: B
Illustration 46: Chlorination of toluene in presence of light and heat followed by treatment with
aqueous NaOH gives
(A) o-Cresol (B) p-cresol
(C) 2,4- dihydroxy toluene (D) Benzoic acid
Solution: D
Illustration 47: Benzoic acid when treated with PCl5 gives
(A) Chlorobenzene (B) Benzyl chloride
(C) Benzoyl chloride (D) Benzene
Solution: C
Illustration 48: Which one of the following compound forms benzoic acid on oxidation?
(A) Chlorophenol (B) Benzyl chloride
(C) Chlorobenzene (D) Chlorotoluene
Solution: B
Illustration 49: Phenyl diazonium does not form azodye with
(A) aniline (B) phenol
(C) N,N-dimethylaniline (D) anisole
Solution: D
Illustration 50: Identify (C) in the following reaction sequence
CH3NH2 OH
CH
C
B
A 3
AgOH
excess
I
CH3





 


 
 
(A) CH3CH2CH2NH2 (B) (CH3)3N
(C) (CH3)2NH (D) (CH3)4 H
O
N

Solution: B

13. Illustration 51: The reagent (X) is
C6H5CH2CONH2 
 
 )
X
(
C6H5CH2CN
(A) P2O5 (B) SOCl2
(C) POCl3 (D) All the above
Solution: D
Illustration 52: Melamine polymer is a copolymer of
(A) melamine and acetaldehyde (B) melamine and formaldehyde
(C) phenol and formaldehyde (D) None of the above
Solution: B
Illustration 53: Identify (Z)
C6H13COCl Z
Y
X Ni
/
H
NH
H
C
,
S
BaSO
/
Pd
/
H 2
2
13
6
4
2


 




 





 


(A) C6H13CH2NHC6H13 (B) C12H25CH2NH2
(C) C6H13-CHNH2
C6H13
(D) (C6H13)2CH3N
Solution: A
Illustration 54: Which of the following will give a positive carbylamine test
1. H3CNH2 2. CH3NHCH3 3. (CH3)3N 4. C6H5NH2
(A) 1 and 3 (B) 2 and 4
(C) 3 and 4 (D) 1 and 4
Solution: D
Illustration 55: Which of the reagent is not used to convert nitrobenzene to aniline
(A) H2/Ni (B) Sn+HCl
(C) SnCl2 in HCl (D) LiAlH4
Solution: D
Illustration 56: Which one of the following is produced by the reduction of RCN in sodium and
alcohol
(A) RCONH2 (D) RCO-NH4
+
(C) RCH2NH2 (D) (RCH2)3N
Solution: C
Illustration 57: In the following reaction, the product (X) is
CHCl3+PhNH2  X + 3Y + 2Z
(A) PhCN (B) PhNC
(C) PhCl (D) PhOH
Solution: B
Illustration 58: Which of the following is weakest base in water
(A) Aniline (B) p-nitoroaniline
(C) Trimethylaniline (D) ammonia
Solution: B

14. Hydrocarbons
1. Point out (A) in the given reaction sequence:
2
3
Δ
O
H
/
O
CO
COOH
CH
2
)
B
(
)
A
( 2
3





 

(A) (B)
(C) (D)
2. End product of the following sequence is:
)
C
(
)
c
(
)
A
(
C
CaO
4
2
2
2
SO
H
Hg
O
H
Heat

 


 


 



(A) Ethanol (B) Ethyl hydrogen sulphate
(C) Ethanal (D) Ethylene glycol
3. 10 mL of a certain hydrocarbon require 25 mL of oxygen for complete combustion and
the volume of CO2 product is 20 mL. What is the formula of hydrocarbon.
(A) C2H2 (B) C2H4
(C) CH4 (D) C2H6
4. Hydrogenation of the compound:
Me
Me
H
H
H
Me
In the presence of poisoned palladium catalyst gives:
(A) An optically active compound (B) An optically inactive compound
(C) A racemic mixture (D) A diastereomeric mixture
5. Ozonolysis of will give
(A) 2 (B)
O
O
(C)
O
(D)
O
2

15. 6. CH3 –
3
CH
|
CH – CH = CH2 + HBr  A (predominant), A is
(A) CH3 – CH – CH – CH3
|
CH3
|
Br
(B) CH3 – CH – CH2 – CH2Br
|
CH3
(C)
CH3 – C – CH2 – CH3
|
CH3
Br
|
(D) None is correct
7. Stability of CH3 – CH = CH – CH3 CH3 – C = C – CH3
|
CH3
(I) |
CH3
(II)
CH3 – C = CH2
(III)
|
CH3
CH3 – C = CH—CH3
|
CH3
(IV)
In the increasing order is
(A) I  III  IV  II (B) I  II  III  IV
(C) IV  III  II  I (D) II  III  IV = I
8
H – C
||
H – C
A
4
KMnO
alkaline




 

|
CH3
CH3
|
Which is true about this reaction?
(A) A is meso 1, 2-butan-di-ol formed by syn addition
(B) A is meso 1, 2-butan-di-ol fomred by anti addition
(C) A is a racemic mixture of d and l, 1, 2-butan-di-ol formed by anti addition
(D) A is a racemic mixture of d and l 1, 2-butan-di-ol formed by syn addition.
9 The treatment of C2H5MgI with water produces
(A) Methane (B) Ethane
(C) Ethanal (D) Ethanol
10. The order of reactivity of halogens towards halogenation of alkanes is
(A) F2 > Br2 > Cl2 (B) F2 > Cl2 > Br2
(C) Cl2 > F2 > Br2 (D) Cl2 > Br2 > F2
11. The chlorination of alkane involves
(A) Cl free radicals (B) Cl+
species
(C) Cl–
species (D) CH3 free radicals
12.
H – C
|| 
 
 2
Br
|
CH3
CH3
|
C – H
H
H
Br
Br
CH3
CH3
(A)

16. Which is true statement?
(A) A is formed by anti addition and is meso
(B) A is formed by syn addition and is meso
(C) A is formed by anti addition and is racemic
(D) A is formed by syn addition and is racemic
13. 2-butene + Br2 
Br
Br
H
H and enantiomer. 2-butene is
(by anti addition)
CH3
CH3
(A) cis (B) trans
(C) both (D) none
14. (A) cis-2-butene I
H
HCO3


 

(B) trans-2-butene 


 

H
HCO3
II
Correct statements are
(A) is racemic mixture by anti addition
(B) II is meso compound by anti addition
(C) I is meso compound by syn addition
(D) II is racemic compound by syn addition
15.
B
OH
/
O
H
THF
/
BH
2
2
3



 
 CH2 
 


O
H3
A
A and B are
(A)
CH2OH
both
(B) CH3
both
OH
(C) CH3
OH
CH2OH, (D) CH3
OH
CH2OH,
,
Alkyl Halide
16. Cl
Br
is
P
.
P
KCN

 

(A)
CN
Br
(B)
Cl
CN
(C)
CN
CN
(D)
NC
CH3

17. 17. (CH3)3CMgCl 
 
 O
D2
A. A is
(A) (CH3)3CD (B) (CD3)3CD
(C) (CH3)3CH (D) (CD3)3CH
18. RMgBr is
P
.
P
O
H
CO
2
2

 

(A) RCO3H (B) RCO2H
(C) RCHO (D) RCOR
19. Addition of HCl to propene involves
(A) CH3 2
H
C

CH2Cl (B) 2
2
3 H
C
CH
CH

(C) Cl
HCH
C
CH 2
3


(D) 3
2
3 CH
H
C
CH 

20.
is
X
.
X
4
LiAlH


 

OTs
(A) (B)
(C) (D)
Li
21. 1-methyl cyclohexene can be converted to 2-methyl 1-cyclohexanol by
(A) Acid catalysed hydration (B) Hydroboration
(C) Oxymercuration demercuration (D) Epoxide formation and then reduction
with LiAlH4
22. Which of the following is the best leaving group?
(A) OAc–
(B) CF3SO3
–
(C) PhSO3
–
(D) OH–
23. Which of the following alcohol can be dehydrated must easily?
(A) CF3CH2OH (B) CF3(CH2)2OH
(C) PhOH (D) PhCH2OH
24. Which of the following does not give ppt. with alcoholic AgNO3
(A)
Cl
(B)
C
H2
Cl
(C)
C
H3
Cl
(D)
C
H2
Cl

18. 25. In SN1 reaction recemisation occurs because of
(A) Carbocation formation (B) Carbanion formation
(C) Enolisationic (D) None of these
26. The halide which undergoes nucleophilic substitution most readily is
(A) p-CH3C6H4Cl (B) o-H3COC6H4Cl
(C) p-ClC6H4Cl (D) p-NO2C6H4Cl
27. Best starting material to synthesize 2-methyl 2-butanoic acid is
(A)
OH
C
H3
C
H3
CH3
(B) C
H3 CHO
(C)
C
H3
O
C
H3
(D)
C
H3
CHO
CH3
28. On conversion into grignard followed by treatment with ethanol, how many alkyl halides
would yield and methyl butane.
(A) 2 (B) 3
(C) 4 (D) 5
29. In protic medium the strongest ncuelphilie is
(A) Cl–
(B) F–
(C) Br–
(D) I–
30. Which one is the strongest base?
(A) C–
H3 (B) –
NH2
(C) OH–
(D) F–
Alcohols, Ethers and Phenols
31. For the preparation of t-butylmethyl ether the correct choice of reagent is
(A) Methoxide and t-butyl bromide (B) Methanol and 2-bromobutane
(C) 2-butanol and methyl bromide (D) t-butoxide and methyl bromide
32.
O
Cl
OEt
-
The product is
(A)
Cl OEt
OH
(B)
Cl OH
OEt
(C)
O
EtO
(D)
O
OEt

19. 33. OH
is
P
.
P
? 3
3 AlCl
Anhydrous
COCl
CH




 



 

(A)
OCOMe
(B)
OH
COMe
(C)
OMe
OH
(D)
OH
COMe
34. OH
is
X
,
X
O
S
K
O
H
OH
8
2
2
3



 


(A)
OH
SO3H
(B)
OH
SO3H
(C)
OH
OH
(D)
OH
OH
35. D
F
D
is
P
.
P
3
2 NH
/
KNH



 

(A)
D
NH2
D
(B)
D
NH2
NH2
(C)
D
H
NH2
(D)
H
F
H

20. 36. OH
is
product
The
.
Br
2
CS
C
0
2 
 

 
(A)
Br
OH
(B)
Br
(C)
OH
OH
(D)
OH
Br
Br
Br
37.
O
CH2
is
P
C
200



(A)
O
CH2
(B)
OH
CH2
(C)
OH
CH2
(D) None of these
38. ?
O
H
RMgX
3



 

O
C
H3
CH3
(A) Ph CH3
R
OH
(B) Ph CH3
OH
OH
(C) C
H3 CH3
R
OH
(D) None of these

21. 39. OH
COOH
+ (CH3CO)2O P is called
(A) Anisole (B) Phenetole
(C) Aspirin (D) Oil of Wintergreen
40.
is
P
KOH
/
CO2




 

OH
OH
(A)
OH
OH
(B)
OH
COOH
(C)
OH
COOH
(D)
OH
CHO
Carbonyl Compounds
41. Cyclohexanone on reaction with Na2CO3 solution forms
(A)
OH
O
(B)
O
(C)
O O
(D)
OH
O
H
42. O
CH3
is the final product obtained when one of the following
is reacted with base?
(A)
C
H3 CH3
O O
(B)
C
H3 CH3
O
O
(C) C
H3 CH3
O
O
(D)
C
H3 CH3
O O

22. 43. Cannizaro reaction is given by
(A) Trimethylacetaldehyde (B) Acetaldehyde
(C) Propanaldehyde (D) Acetone
44. Haloform reaction is not shown by
(A) CH3COCH3 (B) C2H5OH
(C) CH3COOH (D) CH3CHO
45. Ozonolysis of 2-methylbut-2ene yields
(A) Aldehyde only (B) Ketone only
(C) Both aldehyde and ketone (D) None
46. Which of the following reagents does not react with HCHO, CH3CHO and CH3COCH3
respectively, in the same manner?
(A) HCN (B) NH2OH
(C) PhNHNH2 (D) NH3
47.
excess
HIO
3
2
4
CHO
)
CHOH
(
OH
|
CH 
 


 Products
(A) HCHO + 4HCOOH (B) 4HCHO + HCOOH
(C) 2HCHO + 3HCOOH (D) 5HCOOH
48. Which of the following does not undergo aldol condensation?
(A) PhCH2CHO (B) PhCHO
(C) CH3COCH3 (D) (CH3)2CHCHO
49. A new carbon-carbon bond formation is possible
(A) Cannizaro reaction (B) Friedal Craft reaction
(C) Clemmenson reduction (D) None of these
50. Which of the following will react with water most readily?
(A) CHCl3 (B) Cl3CCHO
(C) CCl4 (D) ClCH2CH2Cl
51. Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl
group is
(A) MeCOCl (B) MeCHO
(C) MeCOOMe (D) MeCOOCOMe
52. In a Cannizaro reaction the intermediate that will be the best hydride donor is
(A) O
-
H
OH
(B) O
-
H
O
-
(C) O
-
H
O
-
MeO
(D) O
-
H
O
-
O2N

23. 53. In the transformation
O
H
CH3
O
O
H
CH3
The reagent is
(A) Zn/Hg conc. HCl (B) NH2NH2, OH–
(C) H2/Ni (D) NaBH4
54. Which of the following will decarboxylate on heating?
(A) PhCOCOOH (B) PhCOCH2COOH
(C) CF3 –
||
O
C – CH2COOH (D) CH3CH2
OH
|
CH COOH
55. In Cannizzaro reaction given below
2Ph – CHO 
 


OH
PhCH2OH + PhCO2
–
the slowest step is
(A) Attack of OH–
at the carbonyl group
(B) Transfer of hydride to carbonyl group
(C) Abstraction of proton from carboxylic acid
(D) Deprotonation of Ph – CH2OH
Carboxylic Acids and its Derivatives
56. When sodium formate is heated at 360C, the main product is
(A) Sodium oxalate (B) CO
(C) CO2 (D) Sodium carbonate
57. Sodium acetate on reaction with acetyl chloride gives
(A) CH3COOH (B) Sodium formate
(C) acetic anhydride (D) acetone
58. When sodium formate is heated with soda lime it forms
(A) H2 (B) CH4
(C) C2H6 (D) CHCH
59. When formic acid reacts with PCl5, it forms
(A) acetyl chloride (B) formyl chloride
(C) methyl chloride (D) propionyl chloride
60. When formic acid is heated with conc. H2SO4 it gives
(A) CO2 (B) CH3HSO4
(C) (COOH)2 (D) CO
61. Which one of the following be expected to be most highly ionized in water
(A) CH2ClCH2CH2COOH (B) CH3CHClCH2COOH
(C) CH3CH2CHClCOOH (D) CH3CH2CCl2COOH

24. 62. Mercuric chloride is reduced to mercurous chloride by
(A) acetic acid (B) Carbon tetrachloride
(C) formic acid (D) ammonia
63. The end product in the following sequence is
CH3OH C
B
A O
H
KCN
PCl 2
5

 


 


 

(A) HCOOH (B) CH3COOH
(C) CH3NH2 (D) CH3CONH2
64. Oxalic acid on treatment with conc. H2SO4 gives
(A) CO+H2O2 (B) HCOOH+CO2
(C) HCOOH+O2+CO2 (D) H2O+CO+CO2
65. The product (C) in the reaction is
RCOOH C
B
A 5
2
3 O
P
NH



 




 

(A) RNH2 (B) RCN
(C) RNC (D) RCONH2
66. Which of the following cannot reduce Fehling’s solution?
(A) Formic acid (B) acetic acid
(C) formaldehyde (D) acetaldehyde
67. Formic acid and acetic acid can be distinguished with
(A) Litmus paper (B) Caustic soda
(C) NaHCO3 (D) Ammonical AgNO3
68. RCOOH  RCH2OH
This conversion can be affected by
(A) Zn/HCl (B Na/C2H5OH
(C) Pd/H2 (D) None
69. Acetic acid reacts with chlorine in the presence of catalyst anhyd FeCl3 to give
(A) acetyl chloride (B )methyl chloride
(C) trichloroacetic acid (D) Chloral hydrate
70. The product (X) of the reaction is
CH3CONH2 + HNO2  (X)
(A) CH3NH2 (B) CH3CH2NH2
(C) CH3COOH (D) CH3OH
Amines
71. When aniline is treated with fuming sulphuric acid at 475 K it gives
(A) Sulphanilicacid (B) aniline sulphate
(C) o- aminobenzenesulphonic acid (D) m-aminobenzene sulphonic acid

25. 72. When aniline is treated with bromine water it forms
(A) 2–bromoamiline (B) 4-bromoaniline
(C) mixture of 2 and 4 bromoaniline (D) 2,4,6 -tribromoaniline
73. Hydrolysis of phenyl isocyanide forms
(A) Benzoic acid (B) Formic acid
(C) aniline (D) Acetic acid
74. Towards electrophilic substitution, the most reactive species be
(A) NO2 (B) NH2
(C) NH3
Cl (D) NHCOCH3
75. Acid hydrolysis of benzonitrile forms
(A) benzylamine (B) aniline
(C) benzoic acid (D) phenol
76. For selective reduction of m-dinitrobenzene to m- nitroaniline, the reducing agent is
(A) Sn/HCl (B) Zn/NH4Cl(aq)
(C) (NH4)2S (D) alkaline solution of glucose
77. Aniline on reaction with acetyl chloride forms
(A) phenol (B) acetamide
(C) acetanilide (D) benzene
78. For the conversion of primary amide to amine having same number of carbons, the
reagent will be
(A) Br2+NaOH (B) LiAlH4
(C) H2/Pt (D) Na+C2H5OH
79. Which of the following is not correct regarding aniline?
(A) It is less basic than ethylamine (B) It can be steam-distilled
(C It reacts with sodium to give hydrogen (D) It is soluble in water
80. Which of the following reagents will give methylamine from acetamide
(A) PCl3 (B) NaOH+Br2
(C) Soda lime (D) Hot conc. H2SO4
81. The compound which on reaction with aq. nitrous acid at low temperature produces oily
nitrosamine is
(A) methylamine (B) ethylamine
(C) diethylamine (D) triethylamine
82. The correct order of b.p of the following amines is
1. n-butylamine 2. Ethyldimethyl amine 3.diethylamine
(A) 1>3>2 (B) 1>2>3
(C) 2>3>1 (D) 2>1>3

26. 83. The conjugate acid of HO(CH2)3 NH2 is
(A) H2O+
(CH2)3 NH2 (B) HO(CH2)3 3
H
N

(C) 2
3
2 NH
)
CH
(
O (D) HO(CH2)3 H
N

84. Place the following aromatic amines in the decreasing order of their basicities
1. PhNH2 2.Ph2NH 3.Cyclohexyl-NH2
(A) 3>1>2 (B) 3>2>1
(C) 1>2>3 (D) 1>3>2
85. Identify (Z)
C6H5COOH
3
4
PBr
.
2
LiAlH
.
1


 
 (X) )
Y
(
KCN

 
 )
Z
(
4
LiAlH


 

(A) C6H5CH2NH2 (B) C6H5CH2CH2NH2
(C) C6H5CH2CH2CH2NH2 (D) 2
NH
3
H
I
C
CH
5
H
6
C 

27. Hydrocarbons
1. C 2. C
3. A 4. B
5. B 6. C
7. A 8. A
9. B 10. B
11. A 12. A
13. A 14. C, D
15. D
Alkyl Halides
16. A 17. A
18. B 19. D
20. A 21. B
22. B 23. D
24. D 25. A
26. D 27. C
28. C 29. D
30. A
Alcohols, Ethers and Phenols
31. D 32. D
33. D 34. D
35. D 36. A
37. C 38. A
39. C 40. C

28. Carbonyl Compounds
41. A 42. A
43. A 44. C
45. C 46. D
47. A 48. B
49. B 50. B
51. A 52. C
53. A 54. B
55. A
Carboxylic Acids and its Derivatives
56. A 57. C
58. A 59. B
60. D 61 D
62. C 63. B
64. D 65. B
66 B 67. D
68. D 69. C
70. C
Amines
71. A 72. D
73. B 74. B
75. C 76 C
77. B 78. B
79. D 80. B
81 C 82. A
83. B 84. A
85. B