CARBOXYLIC ACIDS AND
IT'S DERIVATIVE ,
ALIPHATIC AMINES
CONTENTS
EXERCISE - I
EXERCISE - II
EXERCISE- III
EXRECISE - IV(A)
EXRECISE - IV(B)
ANSWER KEY
ORGANIC CHEMISTRY

EXERCISE -I(A)
Q.1 Whichoneofthe following isan acylgroup:
(A) R–O– (B) 

 O
C
R
|
|
O
(C) 
C
R
|
|
O
(D) 

 NH
C
R
|
|
O
Q.2 Inthegivenreaction:
3
5
6 CH
C
H
C
|
|
O






 

H
)
ii
(
KOH
/
Br
)
i
( 2 CHBr3 + [X]
[X]willbe:
(A) C6H5–CHO (B) C6H5COOH (C) C6H5–CH2OH (D) CH3COOH
Q.3 In the reactionsequence :
CH3–CC–H 

 

MgBr
CH3 CH4+ (A) 


 

H
/
O
H
)
ii
(
CO
)
i
(
2
2
(B)
(B)willbe:
(A) CH3–CC–CH3 (B) CH3–CC–MgBr (C) CH3–CC–COOH (D) CH3–CH=CH–COOH
Q.4 Consider thegivenreaction
RCOOAg 
 


/
Br2
R–Br
whichone ofthe following acid willgive maximumyieldofR–Br in the above reaction?
(A)
3
3
CH
|
COOH
CH
CH 
 (B) CH3–CH2–CH2–COOH
(C)
3
3
3
CH
|
COOH
C
CH
|
CH

 (D)Allwillgive same yield
Q.5 Benzoic acid ontreatment with hydrazoic acid inthe presence ofconcentrated sulphuric acid gives:
(A)Benzamide (B) Sodiumbenzoate (C)Aniline (D) C6H5CON3
Q.6 Thegivenreaction
7
3
3
5
2
H
C
|
COOH
C
CH
|
H
C

 




 
 4
2
3 SO
H
.
Conc
/
H
N
7
3
2
3
5
2
H
C
|
NH
C
CH
|
H
C


is called :
(A) Schmidt reaction (B) Cirtius reaction
(C) Hofmannrearrangement (D) Lossenrearrangement

Q.7 Inthegivenreaction:
CH3–CH2–COOH



 

/
Br
)
ii
(
AgNO
)
i
(
2
3 [X]
[X]willbe:
(A) Ethylbromide (B) Propylbromide (C) Propylpropanoate (D)Allofthese
Q.8 Inthereaction sequence:
OH
|
COOH
CH
CH3 
 


[Y]
[Y]willbe:
(A) (B) CH2=CH–COOH
(C) COOH
CH
CH
|
OH
2
2 
 (D)
Q.9 Acetylationreactionwithacetylchloride is carried out in the presence ofwhichsolvent?
(A) HOH (B) CH3OH (C) Pyridine (D) NaOH
Q.10 Inthe reaction:
C6H5–H
3
AlCl
]
X
[


 5
6
2
5
6 H
C
CH
C
H
C
|
|
O



[X]willbe:
(A) C6H5CH2COCl (B) (C6H5–CH2CO)2O
(C) Both(A) and (B) (D) C6H5–CHCl2
Q.11 Inthegivenreaction:
[X] +Acetic anhydride Aspirin
[X]willbe:
(A) Benzoic acid (B) o-methoxybenzoic acid
(C) o-Hydroxybenzoic acid (D) p-Hydroxybenzoic acid
Q.12 The givenreactionis :
C6H5–CHO + C6H5CHO 



 

]
)
CO
(
Fe
[
Na 4
2
5
6
2
5
6 H
C
CH
O
C
H
C
|
|
O



(A) Claissenreaction (B) Tischenko reaction(C) Perkin reaction (D) Cannizzaro reaction

Q.13 Inthegivenreaction:
5
2
3
3 H
OC
C
CH
CH
C
|
|
|
|
O
O




OH
H
C
ONa
H
C
5
2
5
2


 
 [X]
[X]willbe:
(A)
H
|
CH
C
CH
C
|
|
|
O
OH
3
2



(B) 3
CH
C
CH
HC
|
|
O



(C) C
CH
C
CH
|
|
|
|
O
O
2
3 

 (D) COOH
CH
C
CH
|
|
O
2
3 


Q.14 Number ofcross products inthegiven reaction:
CH3COOC2H5 + C6H5–CH2–COOC2H5
OH
H
C
ONa
H
C
5
2
5
2


 

(A) One (B)Three (C) Two (D)four
Q.15 Hofmanndegradationis givenby:
(A) Imide (B)Acid chloride (C)Acid anhydride (D) None ofthese
Q.16 Inthegivenreaction:
N
C
H
C
|
|
O
5
6 
 

 
 4
LiAlH [X]
[X]willbe:
(A) C6H5–CH2OH (B) C6H5COOH (C) C6H5CONH2 (D) C6H5–CH2–N
Q.17 Which one ofthe following compounds gives carboxylic acid with HNO2?
(A) Cl
C
H
C
|
|
O
5
6 
 (B) C6H5CONH2
(C) 3
3 CH
C
O
C
CH
|
|
|
|
O
O



 (D) CH3COOC2H5

Q.18 Inthereaction sequence:
H
C
CH
|
|
O
3 

H
O
HCN

 
 (A)



 


H
/
O
H2
Product
Product willbe:
(A)
H
|
COOH
C
CH
|
OH
3 

(B)
H
|
CH
C
HOOC
|
OH
3


(C) Mixture of
H
|
COOH
C
CH
|
OH
3 
 and
H
|
CH
C
HOOC
|
OH
3


(D) 2
3 CONH
CH
CH
|
OH


Q.19 Inthegivenreaction:
COOH
CH
CH
|
Cl
3 

O
H
)
ii
(
mole
1
NH
)
i
(
2
3


 
 [X]
Product [X]willbe:
(A) -Amino acid (B) -Aminoamide (C) -Amino acid (D) -Aminoamide
Q.20 Whichofthe followingreactions willgive-hydroxyacid asa product:
(A) CH3–CHO






 

/
H
/
O
H
)
ii
(
HCl
/
NaCN
)
i
(
2
(B) CH3–CHO + Br–CH2–COOC2H5





 

/
H
/
HOH
)
iii
(
HOH
/
Cl
NH
)
ii
(
Zn
)
i
(
4
(C) COOH
CH
CH
|
X
2
2 
 


 

HOH
/
NaOH
(D)Allofthese
Q.21 Rochelle salt isdimetalsalt of:
(A)Tartaric acid (B) Citric acid (C) Oxalic acid (D) Salicylic acid

Q.22 Inthegivenreaction:

 
 3
PCl
[X]
[X] willbe :
(A) (B) (C) (D)
Q.23 Sodiumbicarbocate reacts with salicylic acidto form:
(A) C6H5ONa (B) (C) (D)
Q.24 Inthegivenreaction:

 

C
200 [X]
[X]willbe:
(A) Phenylsalicylate (B)Aspirin (C) Phenol (D) Benzoic acid
Q.25 Arrange these estersin decreasing order ofease ofesterfication with CH3OH/H :
(I)
3
3
CH
|
COOH
CH
CH 
 (II)
3
2
3
CH
|
COOH
CH
CH
CH 


(III)
3
3
3
CH
|
COOH
C
CH
|
CH

 (IV) (CH3–CH2)3C–COOH
(A) II > I > III > IV (B) I > II > III > IV (C) III >IV > II > I (D) IV > III > II > I
Q.26 Arrange followingcompounds indecreasing orderofreactivityfor hydrolysisreaction:
(I) C6H5COCl (II) NO2 COCl
(III) CH3 COCl (IV) OHC Cl
C
|
|
O

(A) II > IV > I > III (B) II > IV > III > I (C) I > II > III > IV (D) IV > III > II > I

Q.27 Inthegivenreactionsequence:
CH3–CH2–OH







 


H
)
ii
(
/
H
O
/
KMnO
)
i
( 4
(A)



 

/
NH
)
ii
(
SOCl
)
i
(
3
2
(B) 

 

KOH
/
Br2
(C)
(C) willbe :
(A)Methylamine (B)Eltylamine (C) Propylamine (D)Acetamide
Q.28 Whichone ofthe following onheatinggives unsaturated acid:
(A) -Hydroxyacid (B) -Hydroxyacid (C) -Hyroxy acid (D) -Hydroxyacid
Q.29 Which willformlactone ontreatment with NaOH ?
(A) -Bromo acid (B) -Bromo acid (C) -Hydroxyacid (D) -Bromo acid
Q.30 Whichone ofthe following willgo decarboxylationon heating?
(A) Succinic acid (B) Phthalic acid (C) Malonic acid (D)Adipic acid
Q.31 Inthegivenreaction:
CH3–COOH




 

/
H
/
O
H
)
iii
(
NaCN
)
ii
(
P
/
Br
)
i
(
2
2
[X]
[X]willbe:
(A) CH2 (B) COOH–CH2–CH2–COOH
(C)
CO
CH
|
CO
CH
2
2


(D) CH2
Q.32 Whichopticallyactive compoundonreductionwithLiAlH4 willgive opticallyinactive compound?
(A)
3
3
OCH
|
COOH
CH
CH 
 (B)
OH
|
COOH
CH
CH
CH 2
3 


(C)
OH
CH
|
COOH
CH
CH
CH
2
2
3


 (D)
OH
|
COOH
CH
CH
CH 2
3 


Q.33 Inthegivenreaction:
3
3
2
3
CH
|
CH
CH
C
CH
CH
|
|
O



 


 

COOOH
CF3
[X] as main product
[X]willbe:
(A)
3
3
2
3
CH
|
CH
CH
O
C
CH
CH
|
|
O




 (B)
3
3
2
3
CH
|
CH
CH
O
C
CH
CH
|
|
O





(C) 3
3
3 )
CH
(
OC
C
CH
|
|
O

 (D) (CH3)3COOCH3

Q.34 Whichone ofthe following reactions can be used for the preparation of-hydroxyacid:
(A) Perkinreaction (B) Reformatskyreaction
(C)Aldolcondensation (D) Claisen condensation
Q.35 Which acid canbe oxidised beFehling solution:
(A) Malonic acid (B)Acetic acid (C) Oxalic acid (D) formic acid
Q.36 Inthegivenreaction:

 

HBr
[X]
[X]willbe:
(A) (B) (C) (D)
Q.37 Reducing propertyofformic acid is due to the presence of:
(A) – OH (B) H
C
|
|
O

 (C) OH
C
|
|
O

 (D)Allofthese
Q.38 Inthegivenreaction:


 


H
/
HOH
[X]
[X]willbe:
(A) HOOC–CH2–CH2–CH
|
OH
–CH3 (B) CH3–CH2–CH2–CH2–COOH
(C) HO–CH2–CH2–CH2–COOH (D)
OH
|
COOH
CH
CH
CH
CH 2
2
3 




Q.39 Inthegivenreaction:


 
 4
LiAlH
[A]
[B]
[A] and [B] respectivelybe:
(A)
OH
|
OH
CH
CH
CH
CH
OH
CH 2
2
2
2



 and
(B) and
OH
|
OH
CH
CH
CH
CH
OH
CH 2
2
2
2




(C) Both are
(D) Both are OH
CH
CH
CH
CH
OH
CH
|
OH
2
2
2
2 



Q.40 Inthegivenreaction:
+
5
2
5
2
H
COOC
|
H
COOC


 

Pyridne
[X]
[X] willbe :
(A) (B)
(C) (D)

Q.41 Inthegivenreactionsequence:
COOH
CH
|
COOH
CH
2
2





(A) 




 


 /
NH
CH
CH 2
2
3 (B)
(B)willbe:
(A)
O
|
|
H
C
NH
C
CH
|
H
C
NH
C
CH
|
|
O
5
2
2
5
2
2





 (B)
O
|
|
C
CH
|
C
CH
|
|
O
2
2


(C)
COOH
CH
|
COOH
CH
2
2


(D)
COOH
CH
|
H
C
NH
C
CH
|
|
O
2
5
2
2




Q.42 Inthegivenreaction:
CH3CHO






 

/
H
/
O
H
)
ii
(
HCl
/
NaCN
)
i
(
2
(A)
reagent
Fenton

 
 (B)
(B) willbe :
(A)Acetic acid (B) Oxalic acid (C) Pyruvic acid (D) Citric acid
Q.43 In which reactionproduct is hydrocarbon?
(A) RCOOK 


 

is
Electrolys (B) RCOOAg 
 


/
I2
(C) CH3–CH3 

 

v
h
/
Cl2 (D)
3
3
3
CH
|
Cl
C
CH
|
CH

 

 

OH
H
C 5
2
Q.44 Sodiumbenzoate onheating withsodalime gives:
(A) Benzene (B)Benzophenone (C) Methane (D) Calciumbenzoate
Q.45 Which ofthe following compounds gives carbondioxide with NaHCO3?
(A)Acetic acid (B)Hexanol (C) Phenol (D)Acetylene
Q.46 When propanoic acid is treated with aqueous sodium bicarbonate, carbon dioxide is liberated. The
carbon ofthe CO2 comes from:
(A) Methylgroup (B) Carboxylic group (C) Methylene group (D) Bicarbonate
Q.47 The reduction ofbenzoylchloride with Pd and BaSO4/CaCO3 produces:
(A) Benzylchloride (B) Benzoic acid (C) Benzaldehyde (D)Allofthese
Q.48 Whichone ofthe following esters cannot undergo selfClaisen condensation?
(A) CH3–CH2–CH2–COOC2H5 (B) C6H5COOC2H5
(C) C6H11–CH2–COOC2H5 (D) C6H5–CH2COOC2H5
Q.49 Amides maybe converted into amines bya reaction named after :
(A) Kekule (B) Perkin (C) Hofmann (D) Claisen

Q.50 The treatment ofan ester withLiAlH4 followed byacid hydrolysis produces :
(A) Two aldehyde (B) One carboxylic acid and one alcohol
(C)Two alcohols (D) Two acids
Q.51 Whichofthe following is hydrolysed to give secondaryamine:
(A)Alkylcyanide (B) N
C
H
|
|
O


(C) Nitro paraffins (D)Acid amide
Q.52 N-Ethylpthalimideonhydrolysisgives:
(A) Methylalcohol (B) Ethylamine (C) Dimethylamine (D) Diethylamine
Q.53 Whichaminewillnot react withnitrous acid:
(A) Methylamine (B) Ethylamine
(C) Dimethylamine (D) N, NDimethylethane amine
Q.54 Whichgas willbeevolved out when[CH3CH2NH2 + (CH3)2CHNH2] istreated with sodiumnitrite and
HCl:
(A) Chlorine (B)Ammonia (C) Nitrogen (D) NO2
Q.55 Boiling Ethylamine onreactionwithacidified KMnO4 gives:
(A)Acetaldehyde (B) EthanoicAcid (C)Ethanol (D)Acetamide
Q.56 Methylamine onreaction withchlorine in the presence ofNaOH gives:
(A)Chloroform (B) Methylchloride
(C) N-Methylchloramine (D)Chloramine
Q.57 Highest value ofpKb willbe of:
(A) NH3 (B) (CH3)2NH (C) (CH3)3N (D) CH3NH2
Q.58 Lowest boilingpoint willbe ofthe compound:
(A)Ethylamine (B)Ethylmethylamine
(C) 1-Propaneamine (D) N,N-Dimethylmethaneamine
Q.59 Amines are basic in nature because:
(A) Theyproduce OH– ions when treated with water
(B) Theyhave replaceable H atoms on N atoms
(C) Theyhave lone pair ofelectronon N atom
(D) None ofthese
Q.60 Whichofthe following diazoniumsalt is relativelystable of0-5°C:
(A) CH3–NN}Cl– (B) CH3C(CH3)–NN}Cl–
(C) C6H5–NN}Cl– (D) (CH3)3C–NN}Cl–
Q.61 Alkylaminedissolveinhydrochloricacidtoformalkylammoniumchloride. Thenitrogeninthelattersalt is:
(A) Quadricovalent only (B)Tricovalent only
(C)Unielectrovalent only (D)Quadricovalent, Unielectrovalent
Q.62 Which ofthe following canbe detected bycarbylamine reaction:
(A) Urea (B) CH3CONH2 (C) C2H5NH2 (D)Allofabove

Q.63 Cyanides exists in:
(A)Tautomericform (B)Geometricalform (C) Inboth form (D) None
Q.64 Hydrolysis ofalkylisocyanide yields:
(A) Primaryamine (B)Tert. amine (C)Alcohol (D)Aldehyde
Q.65 Whichofthefollowing compound gives the smellofmustard oil:
(A)Alkylisocyanate (B)Alkylisothiocyanate
(C)Alkylisocyanide (D)Alkylisonitrile
Q.66 The compound obtained bythe reactionbetweenprimaryamine and aldehyde is:
(A)An amide (B)lmine (C) Nitrite (D) Nitro
Q.67 When propionamide reacts with Br2 inthe presence ofalkalithe product is:
(A) CH3CH2CH2NH2 (B) CH3CH2NH2 (C) C3H7CN (D) C2H5CN
Q.68 A reactionofethylamine &acetic anhydride leads to the formationof:
(A) CH3NHCOCH3 (B) C2H5CONHCH3 (C) CH3CONHC2H5 (D) CH3–CH=NOC2H5
Q.69 IdentifyX inthe reaction
heat
KOH
/
CHCl3



 
 Intermediate
K
300
HCl

 
 X
(A) (B) (C) (D)
Q.70 C=S
Heat
HCl
.
conc


 
 A + B
The unknown compoundsAand B in the above reaction are:
(A) Phenylmercaptan and aniline (B) Thiophenoland aniline hydrochloride
(C) C6H5–N=C=S and
—
3
5
6 Cl
}
H
N
H
C

(D) C6H5CH2SH and
—
3
5
6 Cl
}
H
N
H
C

Q.71 Aniline with solid KOH and CS2 gives:
(A) Thiourea (B) Phenylthio urea (C) Phenol (D) Diphenylthio urea
Q.72 2
NH
C
|
|
O


 
 5
2O
P
W
O
H
MgBr
CH
3
3



 
 X
2
2 I
,
)
OH
(
Ca
.)
ppt
yellow
(



 
 Y 


Z
Zis:
(A) 3
CH
C
|
|
O
 (B) COOH
(C) C
|
|
O
(D)

Q.73 Y 



 

2
3
Br
,
KOD
)
ii
(
,
NH
)
i
(
COOH




 

2
3
Br
,
KOH
)
ii
(
,
ND
)
i
(
X, What are X and Y:
Y:
(A) X is NH2; Y is ND2
(B) X is ND2;Y is NH2
(C) both ND2
(D) both NH2
Q.74 Major end product ofthe following sequenceofreactionis:
CH3CH2CH2CONH2




 
 2
2 Cl
,
)
OH
(
Ca
X 
 
 2
HNO
Z
(A) CH3CH2CH2NH2 (B) CH3CH2CH2OH
(C)
OH
|
CHCH
CH 3
3 (D) CH3CH2COOH
Q.75 The bondangles in methane (I), ammonia (II) and trimethylamine (III) increase inthe order:
(A) I > III > II (B) I > II > III (C) II > I > III (D) III > II > I
Q.76 Name the products in the acid-base reaction:
(a) CH3CH2NH2+ HI (b) (CH3)3N + HBr
(A)(a)Trimethylammoniumiodide (b)Trimethylammoniumbromide
(B) (a)Ethylammoniumiodide (b) Methylammoniumbromide
(C) (a)Ethylammoniumiodide (b)Trimethylammoniumbromide
(D)Allofthese
Q.77 Acetic anhydride andammonia gives the product:
(A) CH3CONH2 (B) CH3CONHCH3 (C) CH3CN (D) CH3COONH4

Q.78 The artificialsweetener aspartame (A) is converted to _________ on storage for extended periods of
timeinaqueous solution:
)
A
(
CO
|
Ph
CH
CH
|
|
OCH
C
CH
NH
C
CH
N
H
|
|
|
|
O
O
2
2
2
3
3








(A)
2
2
2
3
2
CO
|
Ph
CH
CH
|
|
OCH
C
CH
NH
C
CH
N
H
|
|
|
|
O
O






(B)
H
CO
|
Ph
CH
CH
|
|
OH
CH
COH
NCH
H
COH
CH
N
H
|
|
|
|
O
O
2
2
2
3
2
2 




(C) + CH3OH
(D) no change, remains as (A)
Q.79 Reductive aminationofAforms:
A:
(A) (B) (C) (D)
Q.80 The synthetic sweeteneraspartame, knowncommerciallyasNutra sweet, is carboxylicacid. Inaqueous
solutiononstandingit changesto:
(A) (B)
(C) (D) no hydrolysis is possible

EXERCISE - I(B)
Q.1 Consider thefollowing statements regardingthefollowingreaction:
C6H5CHO




 

COONa
CH
O
)
CO
CH
(
3
2
3 
 

O
H2
C6H5– CH = CH – COOH + CH3COOH
(A)Acetate ion acts as base in this reaction
(B) The anhydride having atleast one-hydrogen, provides anenolate for the reaction
(C) The acetate deprotonates the anhydride to formthe nucleophile needed for the reaction
(D) EtONa can also be use as base
Q.2 Which of thefollowing will liberateCO2 onreaction withNaHCO3
(A) OH (B) CH3COOH
(C) (D)
OH
CH
|
OH
CH
2
2
Q.3 RCOOR' can be prepared by:
(A) esterificationofRCOOH
(B) esterificationof(RCO)2O
(C) Baeyer-Villiger oxidation ofRCOR' withperoxyacid
(D) reaction ofRCOClwith R'OH
Q.4 Inthe Hofmannbromamide degradationrecation
2
NH
C
R
|
|
O

 + KOH + Br2 
Intermediates are:
(A) RCONHBr (B) RNCO (C) RNH2 (D) None
Q.5 C4H11N + HNO2  C4H10O (3° alcohol)
(X)
hence Xwillgive:
(A) carbylamine reaction
(B) Hofmannmustard oilreaction
(C) diazoniumsalt (as the intermediate) withHNO2
(D) base insolubleproduct withHinsburg reagent
Q.6 Mixture of 1°, 2° and 3° amines canbe separated by:
(A) Hinsberg's method (B) Hofmann'sisocyanide test
(C) fractionaldistillation (D) NaNO2 HCl

Q.7 Which is/are correct reaction(s):
(A) Cl + NH3  + NH4Cl
(B) Cl + 2NH3  NH2+ NH4Cl
(C) Cl + NH3  + NH4Cl
(D) NH2 + HNO2



C
0
Q.8 Whichofthefollowing compounds willgive aceticacid withKMnO4/H/:
(A) CH3–CHO (B) CH3–CH=CH–CH3
(C) CH3–CC–CH3 (D) CH3CH2OH
Q.9 Acetic acid can be used for the preparation of:
(A)Ethane (B) Methane (C)Acetone (D)ethanol
Q.10 Which one ofthe following acidswillformacetylchloride withPCl5?
(A) MeCOOH (B) MeCOOMe
(C) MeCOOCOMe (D) Me–CONH2
Q.11 Consider thefollowingreaction:
OH
CH
OH
C
CH
|
|
O
3
3 


 



H
HOH
CH
O
C
CH
|
|
O
3
3 



True about theabove reaction is:
(A) Product ishaving smelllike fruits
(B) Nucleophilic additionfollowed byeliminationreaction
(C) followsAAC' mechanism
(D) it is irriversible reaction
Q.12 Inthegivenreaction:
RCOOAg + X2 


R–X+CO2 + AgX
X2 can be:
(A) Cl2 (B) Br2 (C) I2 (D) F2
Q.13 Which one ofthe following compounds willgive HVZ reaction?
(A) (B)
(C) (D)
Q.14 Sodiumsalt ofwhich one ofthe monobasic acids onelectrolysis does not give hydrocarbon:
(A) C6H5COOH (B) HCOOH
(C) Me3C–COOH (D) COOH–CH=CH–COOH

Q.15 Whichone ofthe following acids undergoes decarboxylationonstrong heating:
(A) Pyruvic acid (B) 3-butenoic acid (C) Formic acid (D) Salicylic acid
Q.16 Whichone ofthe following compounds is least reactive with water?
(A) Cl
C
CH
|
|
O
3 
 (B) 2
5
6 NH
C
H
C
|
|
O

 (C) 2
3 NH
C
CH
|
|
O

 (D) Cl
C
H
C
|
|
O
5
6 

Q.17 Acetic anhydride is used as:
(A) Solvent (B)Dehydrating agent (C)Acetylatingagent (D)Anticeptic
Q.18 Inthegivenreaction:
OH
C
R
|
|
O

 


]
X
[
3
CH
O
C
R
|
|
O



[X]willbe:
(A) CH2N2 (B) CH3OH/H (C) MeCOOH (D) Me2SO4
Q.19 Whichofthe following gives silvermirror test?
(A) HCOOH (B) CH3COCHOHCH3
(C) Tartaric acid (D) Glucose
Q.20 An example ofa primaryamine is:
(A) n-Propylamine (B) Isopropylamine (C) t-Butylamine (D) Sec. butylamine
Q.21 Whichcompound is soluble inwater:
(A) [(CH3)2NH2]+ Cl– (B) [CH3NH3]+Cl–
(C) [(CH3)3NH]+ Cl– (D) PhNO2
Q.22 Which compound willliberate CO2 fromNaHCO3 solution:
(A) CH3CO NH2 (B) CH3NH2 (C) (CH3)4N+OH– (D) CH3N+H3Cl–
Q.23 Whichofthe followingcompound canbe produced if1-propane amine is treated withNaNO2 and HCl
(A) Propane-1-ol (B) Propane-2-ol (C) 2-Chloropropane (D) 2-Propaneamine
Q.24 Which ofthe following amine does not react with Hinsbergreagent to give basesoluble product
(A) Neopentylamine (B) secpropylamine (C) diethylamine (D)Ethylmethylamine
Q.25 Ethylamine canbe prepared by
(A) Curtius reaction (B)Hofmannreaction (C) Mendius reaction (D)Reductionofformaldoxime
Q.26 The presence ofprimaryamines can be confirmed in laboratoryby:
(A) Reactionwith HNO2 (B) reactionwith CHCl3 and alc. KOH
(C) ReactionwithGrignard reagent (D) Reactionwith acetylchloride

Q.27 Select correct statement (s):
(A) Cyclohexanoneis oxidised to caprolactonewhich is hydrolysed under the reactionconditions
(B) Baeyer-Villigeroxidationinvolves migrationofH/alkyl/arylgroupswhichisinorder H>tert-alkyl>
sec-alkyl> phenyl> primaryalkyl> methyl
(C) Pinacolone
O
|
|
CCCH
)
CH
( 3
3
3
is oxidised to t-butyl acetate byC6H5CO3H
(D)Allofthe above are correct statements
Q.28 Following equilibriumisfavoured in the forwardside because of:

 


O
H3 + (CH3)3COH
(A) (CH3)3COr (alkoxide ) – a strong nucleophile is formed
(B) (CH3)3C(carbocation) is formed
(C) formed is stabilised byresonance
(D) (a weak acid) is formed
Q.29 ColumnI ColumnII
(organic compounds oxidised by HIO4) (products of HIO4 oxidation)
(A) CH3COCHO (P) PhCH = O + HCOOH
(B) 1,2-cyclohexane dione (Q) CH3CH2CHO + HOOCCH3
(C) PhCH (OH) CHO (R) HOOC (CH2)4COOH
(D) CH3CH2CH (OH) COCH3 (S) CH3COOH + HCOOH
Q.30 ColumnI ColumnII
(A)
O
O
|
|
|
|
H
C
O
C
C
H
H
OC
C
H
C 5
2
3
5
2
5
6 




  (P) Anhydrous ZnCl2
O
O
|
|
|
|
OH
H
C
H
OC
C
CH
C
H
C 5
2
5
2
2
5
6 




(B)
O
|
|
OH
C
C
H3 
 + Cl2 
O
|
|
OH
C
ClCH2

 (Q) C2H5Or
(C) C6H6+(H3C–C=O)2O 
O
|
|
CH
C
H
C 3
5
6

 (R) Red P
(D)  CH3CH(OH)CH2CH2CH2OH (S) LiAlH4

Q.31 ColumnI ColumnII
(Reagents reacting with PhCH2COOH) (Product formed)
(A) CH3MgBr (P) PhCH2COCl
(B) PCl5 (Q) PhCH2COOCH3
(C) NH3, followed byheating (R) CH4
(D) CH3OH in the presence ofconc. H2SO4 (S) PhCH2CONH2
Q.32 Column I (Reactions) Column II (Products)
(A) 2CH3CH2NH2 + (P) N = CH
(B) (CH3)2NH + C6H5COCl (Q) (CH3)2N—
(C) + (R) (CH3)2N–C
|
|
O
(D) CH3CH2NH2 + SO2Cl (S) 
O
C
CH
CH
C
NH
H
C
|
|
|
|
O
O
2
2
5
2 



Q.33 ColumnI ColumnII
(A) R'NH2 



 

 HCl
NaNO2 (P) RR'N–N= O
(B) PhNH2 



 

 HCl
NaNO2 (Q) Ph–N+  NCl–
(C) PhN(CH3)2 



 

 HCl
NaNO2 (R) (CH3)2N N=O
(D) RR'NH2 



 

 HCl
NaNO2 (S) R'OH + N2
Q.34 ColumnI ColumnII
(A) PhCONH2  PhCH2OH (P) B2H6 AcOH H2O
(B)  CH2OH–(CH2)2–CHOH–C6H5 (Q) LiAlH4
(C) C6H5CH = CH– COOH C6H5 – CH = CH2OH (R) H2Pd BaSO4
(D) CH3COCl  CH3–CHO (S) None
Q.35 ColumnI ColumnII
(A) RCN 

 

reduction (P) 1°Amine
(B) RCN
O
H
)
ii
(
MgBr
CH
)
i
(
2
3



 
 (Q) Alcohol
(C) RNC 

 

hydrolysis
(R) Ketone
(D) RNH2 
 
 2
HNO
(S) Acid

EXERCISE - II
Complete the following equation by writting the missing A, B, C, D..................etc.
Q.1 HCCH
excess
COOH
CH3



 
 (A) 


B + C 
 

HOH
CH3COOH
Q.2 Ester (A) 
 
 5
PCl
B + C 

 

KOH
.
aq
(CH3)2CHCH2OH
(D) 

 
 4
LiAlH (CH3)2CHCH2OH
Q.3 R–COOH


 
 3
ND
(A)



 

KOH
,
Br2 (B) 


 

HCl
NaNO2 (C)
Q.4 A 


 

O
Ag
Moist 2 B 

]
O
[
C 

D
(HCOO)2Ca 


G
2
5
2
SOCl
,
2
OH
H
C
/
Na



 
 H 

I
CH3CN 
 


O
H3
X
J 
 


O
H3
Q.5 Acid (A) 
 
 2
SOCl
C
B
Q.6 O 
 
MeOH
A 
 
 3
PCl
B 

 
 2
MeNH
C
Q.7 O = + A  O = + B  O = (uriede)
O =
Q.8 CaCN2 + HOH
)
O
H
(
SO
H
2
2
4
2


 
 (A) 



 

)
H
COOC
(
CH 5
2
2 (B)
Q.9 


A 


B
Q.10 


A + B
Q.11 


H (A)

Q.12 PhMe + (A) 
 
 3
AlCl
p–MeC6H4–CO–CH2–CH2COOH 


 

HCl
/
Hg
/
Zn
(B)
Q.13 CH3(CH2)14CH2CH2COOH 

 
 3
2 PBr
/
Br
(A) 



 

H
)
ii
(
KOH
.
Alk
)
i
(
(B) 


)
C
(
CH3(CH2)14COOH 



 


2
Br
)
ii
(
Ag
)
i
(
(D)
Q.14 

 
 4
LiAlH (A) 
 

HCl (B) 


)
C
(


 
BaO
(D) + CO2+H2O
Q.15 + 

(A) (limited)
Pd
/
H2


 
 (B)
Q.16 
 


OH
(A) 
 


OH
(B) 


 

O
H
)
ii
(
O
H
)
i
(
3
2
(C)
Q.17 HCCH
2
CO
2
)
ii
(
Na
2
)
i
(


 
 (A)
4
2
BaSO
Pd
/
H


 
 (B) C 


D
Q.18 Phthalic acid + NH3  D 


E
Q.19 MeCH(CH2COOH)2




 

O
)
CO
CH
( 2
3 F
Q.20 N
C
CH
|
|
|
H
O
3 
 

 
 4
LiAlH
(A)
Q.21 

 
 4
LiAlH
(B)
Give the mechanism for the reaction with suitable examples:
Q.22
2
NH
C
R
|
|
O

 + 


 


KOH
4
/
Br2 R–NH2
Q.23 '
OR
C
R
|
|
O

 
 

NaOH RCOONa + R'OH

Q.24 '
OR
C
R
|
|
O

 MeCOOEt
RONa

 
 5
2
2 H
OC
C
CH
C
R
|
|
|
|
O
O




Q.25 3
HN
OH
C
R
|
|
O


 

 
 4
2SO
H RNH2
Q.26 Cl
C
R
|
|
O

 
 
 3
AlCl
5
6H
C
C
R
|
|
O


Q.27 Cl
C
R
|
|
O

 + CH2N2
O
H
)
ii
(
Ag
)
i
(
2

 
 R–CH2–COOH
Account for following:
Q.28 Fluoro aceticacid is stronger thanchloro acetic acid.
Q.29 C–O bond lengthin formic acid are 1.23 Å and 1.36 Å but insodiumformate bothcarbonand oxygen
bonds have same value i.e. 1.27 Å.
Q.30 Acetic acid can be halogenated in presence of phosphorous and chlorine but formic acid cannot be
halogenated inthe same way.
Q.31 The C–G bond in acid derivative is expected to be shorter and stronger thanalkylderivative.
Q.32 An acylchloride undergoes nucleophilic attack more rapidlythan doesanalkylhalide.
Q.33 Primaryandsecondaryamide exist as dimer in solid and pure liquid state.
How will you bring about the following transformation:
Q.34 Propanoic acidinto lactic acid.
Q.35 Nitroethane to acetic acid.
Q.36 Benzoic acidto benzamide.
Q.37 Ethylbenzene to 2-phenylpropionic acid.
Q.38 Acetamide fromacetone.
Q.39 Tartartic acid fromethylene.
Q.40 Lactic acid fromacetic acid.
Q.41 Pyruvic acid fromethylbromide.
Q.42 -hydroxypropionic acidfromethylene oxide.

EXERCISE - III
Q.1 Show bya series of equations how you could synthesize each of the following compounds from the
indicated starting materialand anynecessaryorganicor inorganic reagents.
(a) 2-Methylpropanoic acidfromtert-butylalcohol
(b) 3-Methylbutanoic acidfromtert-butylalcohol
(c) 3,3-Dimethylbutanoic acid fromtert-butylalcohol
(d) HO2C(CH2)5CO2H from HO2C(CH2)3CO2H
(e) 3-Phenyl-1-butanolfrom
5
6
2
3
H
C
|
CN
CHCH
CH
(f) fromcyclopentylbromide
(g) from(E)–ClCH=CHCO2H
Q.2 On standing indilute aqueous acid, compoundAis smoothlyconverted to mevaionolactone.



 


)
ii
(
O
H
)
i
( 3
Suggest a reasonable mechanismfor this reaction. What other organic product is also formed?
Q.3 Suggest reactionconditions suitable for the preparation ofcompoundAfrom 5-hydroxy-2-hexynoic
acid.
OH
|
H
CCO
C
CHCH
CH 2
2
3  
5-Hydroxy-2-hexynoic acid Compound A
Q.4 Outline reasonable mechanismfor eachofthe following reactions
(a) + BrMgCH2CH2CH2CH2MgBr
O
H
)
ii
(
THF
)
i
(
2


 

(b) 


Q.5 IdentifycompoundsAthroughC inthe following equations:
(a) CH3O CCl
|
|
O
+
OH
|
CCH
|
|
O


 

pyridine
compound A(C
A(C22H18O4)

(b) 3
2
2
2
3 CH
COCH
CH
CCH
CH
|
|
|
|
O
O








 

ether
diethyl
)
equiv
.
1
(
MgI
CH3 compound B (a lactone, C6H10O2)
(c) 
 

heat compound C (C9H4O5) + H2O
Q.6 Anorganic compound C4H6O4 (A) whenheatedwithaceticanhydride give anothercompound C4H4O3
(B) whichinturnreact withammonia to give athird compound C4H5O2N (C). Both(B)and (C)maybe
hydrolysed toA. With chlorineAgivemonochloro-compound (D) which reacts withcaustic potash to
give either C4H4O5K2 (E) or C4H2O4K2 (F) depending upon the condition of reaction. Identify the
compoundAto F.
Q.7 An organic compoundA(C4H9NO) on treatment with bromine and alkaliform another compound B
(C3H9N) on treatment with sodium nitrite and dilute hydrochloric acid. B yield C (C3H8O). C can be
oxidizedto D(C3H6O).Whichcanalso synthesisedfrommethylacetylene. IdentifythecompoundAto D.
Q.8 With bromine and caustic potash the straight chain compound C4H9ON (A) give C3H9N (B), with
caustic soda C4H7O2Na (C) and with phosphorous pentoxide gives C4H7N (D). With hydrochloric
acid D give C4H8O2 (E) ofwhichC is the sodiumsalt. Bmaybe converted to analcohol(F) andthen to
a halide the grignard reagent from which react with carbon dioxide to give E. On oxidation F give.
Identifythe compoundAto H.
Q.9 Compound (A) with an empirical formula, C7H9N on diazotization give a product which undergoes
reactionwith Cu2Cl2 &HClto give acompound (B). B onoxidation give a compound (C). Compound
(A) on treatment with Br2/H2O formC7H6NBr3 (D). Give the structuralformula ofA, B, C & D.
Q.10 An organic compoundA(C3H5N) on boiling with alkaligive ammonia and sodiumslat of an acid B
(C3H6O2)Aon reduction give a compound C (C3H9N) which with nitrous acid give D (C3H8O). Give
the structuralformula ofA, B, C and D.
Q.11 An organic compound (A) C3H7ON onheating with POCl2 give a compound B whichon hydrolysis
give acompound (C) C3H6O2 withthe liberationofammonia. CompoundAon treatment with LiAlH4
form compound C3H9N (D). Compound D treating with HNO2 liberate N2 gas on refluxing with
chloroformand alcoholic KOH givecompound E whichhavefoulsmell. IdentifycompoundA,B, C, D
and E.
Q.12 An organic compoundA(C8H8O) antreatment with NH2OH. HClgive B and C. Compound B and C
can be converted into D and E respectivelybytreatment ofH2SO4. Compound B, C, D and E are all
isomer ofmolecular formula C8H9NO. When D is boiled with KOH, and oil F (C6H7N) separate out.
F react rapidly with CH3COCl to give back (D). Onother hand. E on boiling with alkalifollowed by
acidification give a white solid G (C7H6O2). IdentifyAto G.
Q.13 An organic compoundA, (C8H9NO) on heating with conc. H2SO4 give another isomer of(A) i.e. (B)
C8H9NO. Compound B on hydrolysis with dil HCl give an aliphatic acid C, C2H4O2 and (D) on
treatment withNaNO2 HClat 0°C give a compound (E) whichgive a white ppt. ofAgClonaddition of
AgNO3. Compound (E) react with alkaline -naphtholto produce orange dye what are to E.
Q.14 Anorganic compoundAofthe molecular formula C4H8O3 give effervescence withsodiumbicarbonate
solutionand canbe acetylated. It canbe separated into dextro and laevoisomers onheatingit formsan
acid B with formula C4H6O2. Compound B give positive Bayer's test. IdentifyAand B.

Q.15 An aromatic compound A, C8H5NO2 can be condensed with an acid derivative (B) C7H11O4 Br in
presence of alkali to form compound (C), C15H15NO6. Compound (B) canbe prepared byaction of
sodiumfollowed bybromine gasondiethylmalonate. Compound (C) condensedagainwithethylchloro
acetate in presence of sodium to give compound (D) C19H21NO8. D on heating with a base can be
converted into E and a salt of acid F (C8H6O4). Compound A can be obtained by heating F with
ammonia. E onboiling with mineralacid produce amino acid G (C4H7NO4). IdentifyAto C.
Q.16 An organic acidA(C3H4O3) is catalyticallyreduced in presence of ammonia to give (B) C3H7NO2. B
react with acetyl chloride hydrochloric acid and alcohol. It can also react with nitrous acid to give
another compound (C) C3H6O3 along withevolution ofN2. What are (A), (B) and (C)?
Q.17 A dibasic acid (A), C4H6O6, on heating with KHSO4 give a monobasic acid (B), C3H4O3, with the
elimination ofCO2 and H2O.Acid (B) on reduction give another monobasicacid (C), C3H6O3. Both
(B) and (C) on heating with I2 and NaOH solution give yellow precipitate of iodoform and sodium
oxalate. Acid (A) react with two moles of acetyl chloride, while (C) reacts with one mole of acetyl
chloride.Acid (A) reacts withfourmoles ofHI to formsuccinic acid, while(C) react withtwo moles of
HI to givepropionic acid. IdentifyA, B, C and give equationfor reaction.
Q.18 An organic compoundofthe formula C3H6O (A) gaveiodoformtest but not Tollen's and Fehling tests.
Two molecules of(A) condenes inpresence ofdryHClgas to yield (B)offormula C6H10O. Compound
(B) decolourised Br2/CCl4 and cold dilute neutral KMnO4, but no ppt. with ammonicalAgNO3 or
CuClsolution. It gave iodoformtest andpotassiumsalt ofa compoundonheating withI2 andKOH. The
potassium salt on treatment with H2SO4 gave compound (C) offormula C5H8O2.Compound (C) on
heating with sodalime gave (D) of formula C4H8. Identify compound Ato D & write the chemical
equation.
Q.19 Anorganic compound(A)offormula C3H6O froma monoxime withhydroxylamineand formiodoform
onheating withI2 andNaOH and sodiumacetate. CompoundAonreactionwith NaCN anddil. H2SO4
gave product B. Which on hydrolysis produced (C). Compound (C) on heating gave (D), which on
decarboxylation gave (E) of formula C3H6. Compound (E) on ozonolysis gave one molecule of
acetaldehyde and one of methanal. What areAto E?
Q.20 Two moles ofan ester (A) are condensed inthe presence ofsodiumethoxide to give a-keto ester (B)
and ethanol. Onheating inanacidic solution(B) gives ethanoland-keto acid(C). Ondecarboxylation
(C) gives 3-pentanone. Identify(A), (B)and (C) withproperreasoning. Name the reactioninvolved in
the conversion of(A) to (B).
Q.21 An acidic compound (A), C4H8O3 loses its optical activity on strong heating yielding (B), C4H6O2
which reacts readily with KMnO4. (B) forms a derivatives (C) with SOCl2, which on reaction with
(CH3)2 NH gives (D). The compound (A) on oxidation with dilute chromic acid gives an unstable
compound (E) whichdecarboxylatesreadilyto give(F), C3H6O. Thecompound(F)givesa hydrocarbon
(G) ontreatment with amalgamated Znand HCl. Give structures of(A) to (G) with proper reasoning.
Q.22 Anorganiccompound (A), C5H8O3 onheating withsoda-lime gives(B),whichreacts withHCNto give
(C). The compound (C) reacts withthionylchloride to produce (D), which onreactionwithKCN gives
compound (E). Alkaline hydrolysis of (E) gives a salt (F), which on heating with soda-lime
produces-butane. Carefuloxidationof(A)withdichromategivesacetic andmalonicacid. Givestructures
of(A) to (F) with proper reasoning.
Q.23 An acid (A), C8H7O2 Br on bromination in the presence of FeBr gives two isomers, (B) and (C) of
formula C8H6O2Br2. Vigorous oxidationof(A), (B) and (C) gives acids (D), (E) and (F) respectively.
(D), C7H5O2Br is thestrongest acid among allofits isomers, whereas (E) and (F) eachhas a molecular
formula ofC7H4O2Br2. Give structures of(A) to (F) withjustification.

EXERCISE - IV (A)
Q.1 The reaction of 2
NH
C
R
|
|
O

 with a mixture of Br2 and KOH gives R–NH2 as a product. The
intermediates involved inthis reactionare: [IIT 1992]
(A) NHBr
C
R
|
|
O

 (B) R–N=C=O (C) R–NHBr (D) N
C
R
|
|
O


Q.2 Which ofthe following carboxylic acidsundergo decarboxylationeasily: [IIT 1995]
(A) C6H5CO–CH2COOH (B) C6H5COCOOH
(C)
OH
|
COOH
CH
H
C 2
5
6  (D)
2
2
5
6
NH
|
COOH
CH
H
C 
Q.3 The molecularweight ofbenzoic acid inbenzene as determinedbydepressionin freezing point method
corresponds to : [IIT 1996]
(A) Ionizationofbenzoic acid (B) Dimerisationofbenzoic acid
(C) Trimerisationofbenzoic acid (D) Solvationofbenzoic acid
Q.4 When propionic acid is treated with aqueous NaHCO3, CO2 is liberated. The 'C' ofCO2 comes from
(A) Methylgroup (B) Carboxylic acid group
(C) methylene group (D) bicarbonate [IIT 1999]
Q.5 Benzoylchloride is prepared frombenzoic acid by: [IIT 2000]
(A) Cl2, hv (B) SO2Cl2 (C) SOCl2 (D) Cl2, H2O
Q.6 Whichofthefollowing acids has thesmallest dissociation constant? [IIT 2002]
(A) CH3CHFCOOH (B) FCH2CH2COOH (C) BrCH2CH2COOH(D) CH3CHBrCOOH
Q.7 Hydrolysis
Acidic

 

Products formed byP & Q can be differentiated by [IIT 2003]
(A) 2 & 4 DNP (B) Lucas reagent (ZnCl2)conc. HCl
(C) NaHSO3 (D) Fehlingssolution
Q.8 When benzamid is treated withPOCl3, the product is: [IIT 2004]
(A)Benzonitrile (B)Aniline (C) Chlorobenzene (D)Benzylamine
Q.9 Whichofthefollowing is obtained when4-Methylbenzenesulphonic acid is hydrolysed with excess of
sodiumacetate? [IIT 2005]
(A) CH3
a
N
O
CO
— 
(B) CH3 + SO3
(C) CH3
a
N
SO3


+ CH3COOH (D) CH3 SO2O. COCH3 + NaOH

Q.10 The correct IUPAC name of C6H5COClis
(A) Benzoylchloride (B) Benzenechloro ketone
(C) Benzenecarbonylchloride (D) Chloro phenylketone [IIT 2006]
Q.11 Whichofthefollowingreactantsonreactionwithconc. NaOHfollowedbyacidificationgivesthefollowing
lactone as the onlyproduct? [IIT 2006]
(A) (B) (C) (D)
EXERCISE - IV (B)
Q.1 Compound(A)(C6H12O2)onreductionwithLiAlH4 yieldedtwo compounds(B)and(C). Thecompound
(B) onoxidationgave (D)whichontreatment withaqueousalkaliand subsequent heatingfurnished (E).
The latter on catalytic hydrogenation gave (C). The compound (D) was oxidised further to give (F)
which was foundto be monobasic acid(molecular mass = 60.0). Deduce the structure of(A), (B), (C),
(D) and (E). [IIT 1990]
Q.2 In the following reactions, identifythecompounds (A), (B), (C)and (D) [IIT 1994]
PCl5 + SO2  (A) + (B)
(A) + CH3COOH  (C) + SO2 + HCl
2(C) +b (CH3)2Cd  2(D) + CdCl2
Q.3 Complete the followingequations bywriting the missingAand B [IIT 1995]
(i) CH3CH2COOH 
 
 2
Br
/
P
(A)






 

H
)
ii
(
)
excess
(
KOH
.
Alc
)
i
( (B)
(ii) C4H8O3(A) 
 
 3
CrO (B) 
 

Warm
2
3
3 CO
CH
C
CH
|
|
O



Q.4 A mixture ofan acid anhydride (A) and a monobasic acid (B) on heating produces another monobasic
acid (C) ofequivalent weight 74and ananhydride (D). The acids and anhydridesremain inequilibrium.
The anhydride (D) contains two identicalfluoro-alkylgroups. The acid (B) contains a trifluoromethyl
group andhasanequivalent weight of128. Give structures of(A)to (D) withproper reasoning. (Atomic
weight offluorine = 19). [IIT 1998]
Q.5 IdentifyAand B inthefollowing equations: [IIT 1999]
CH2 
 

NaOEt (A) (B)





 

H
)
ii
(
OH
)
i
(
O
|
|
OH
C
CH
|
OH
C
CH
C
H
|
|
O
2
3






Q.6 Write the structure ofproductA& B: [IIT 2000]
5
2
18
3
H
C
O
C
CH
|
|
O

 
 


O
H3
A + B
Q.7 IdentifyX,Yand Z in thefollowing synthetic scheme andwrite their structure. Explainthe formationof
labelled formaldehyde (H2C*O) as one of the products when compound Z is treated with HBr and
BaC*O3 + H2SO4 C (gas) [C* denotes C14] [IIT 2001]
Br
CH
CH2 





 

O
H
)
iii
(
X
)
ii
(
ether
/
Mg
)
i
(
3
Y 

 
 4
LiAlH
Z
Q.8 Mention two esters produced when a racemic mixture of2-phenylpropanoic acid is treated with (+)
2-butanol. What is the stereochemicalrelationshipbetween these esters? [IIT 2003]
Q.9 Give major productsA, B, C and D in following reaction sequence. [IIT 2004]
DMF
KCN

 
 A





 

/
PhCHO
)
ii
(
EtOH
/
NaOEt
)
i
(
B 
 


O
H3
C
D

ANSWER KEY
EXERCISE -I(A)
Q.1 C Q.2 B Q.3 C Q.4 B Q.5 C Q.6 A Q.7 A
Q.8 D Q.9 C Q.10 C Q.11 C Q.12 B Q.13 C Q.14 C
Q.15 A Q.16 D Q.17 B Q.18 C Q.19 A Q.20 A Q.21 A
Q.22 B Q.23 B Q.24 A Q.25 A Q.26 A Q.27 A Q.28 B
Q.29 D Q.30 C Q.31 A Q.32 C Q.33 A Q.34 B Q.35 D
Q.36 B Q.37 B Q.38 A Q.39 A Q.40 B Q.41 B Q.42 C
Q.43 A Q.44 A Q.45 A Q.46 D Q.47 C Q.48 B Q.49 C
Q.50 C Q.51 B Q.52 B Q.53 D Q.54 C Q.55 A Q.56 C
Q.57 A Q.58 D Q.59 C Q.60 C Q.61 D Q.62 C Q.63 A
Q.64 A Q.65 B Q.66 B Q.67 B Q.68 C Q.69 D Q.70 C
Q.71 D Q.72 C Q.73 A Q.74 C Q.75 A Q.76 C Q.77 A
Q.78 C Q.79 C Q.80 C
EXERCISE - I(B)
Q.1 A,B,C Q.2 B,C Q.3 A,B,C,D Q.4 A,B
Q.5 A,B,C Q.6 A,C Q.7 A,C,D Q.8 A,B,C,D
Q.9 A,B,C,D Q.10 A,B,C Q.11 A,B Q.12 A,B
Q.13 B,C Q.14 B,C Q.15 A,B,C,D Q.16 B
Q.17 A,B,C Q.18 A,B,D Q.19 A,B,C,D Q.20 A,B,C,D
Q.21 A,B,C Q.22 D Q.23 A,B,C Q.24 A,B
Q.25 A,B,C Q.26 B Q.27 D Q.28 B
Q.29 (A) S, (B) R, (C) P, (D) Q
Q.30 (A) Q, (B) R, (C) P, (D) S Q.31 (A) R, (B) P, (C) S, (D) Q
Q.32 (A) Q, (B) S, (C) P, (D) Q Q.33 (A) S, (B) Q, (C) P, (D) R
Q.34 (A) S, (B) Q, (C) S, (D) R Q.35 (A) P, (B) R, (C) P,S, (D) Q
EXERCISE - II
Q.1 (A) CH3CH(OOCCH3)2; (B) CH3CHO; (C) (CH3CO)2O
Q.2 (A) (CH3)2CHCOOCH2CH(CH3)2 ; (B) (CH3)2CHCOCl; (C) (CH3)2CHCH2Cl
Q.3 (A) RCOND2; (B) RNH2; (C) ROH
Q.4 (A) CH3Cl; (B) CH3OH; (C) HCOOH; (D) Ca(OH)2; (G) HCHO; (H) CH3Cl; (I) KCN; (J) CH3CN;
(X) CH3COOH
Q.5 (A) CH3COOH; (B) CH3COONa; (C) CH3COCl; (E) (CH3CO)2O
Q.6 (A) HOOCCH2CH2COOMe; (B) ClOCCH2CH2COOMe; (C) MeNHOCCH2CH2COOMe
Q.7 (A) 2NH3; (B) CH3COCl; (C) H2SO4 + SO3
Q.8 (A) H2NCONH2; (B) O = Q.9 (A) ; (B)
Q.10(A) (B) Q.11 (A)

Q.12 (A) ; (B) p-MeC6H4CH2CH2CH2COOH
Q.13 (A) CH3(CH2)14CH2CHBrCOOH; (B) CH3(CH2)14CH=CHCOOH; (C) KMnO4;
(D) CH3(CH2)14Br
Q.14 (A) ; (B) ; (C) CN–/H3O+ ; (D)
Q.15(A) ; (B) Q.16 (A) ;(B) ;(C)
Q.17 (A)
COOH
C
|
|
|
COOH
C ; (B)
COOH
C
H
|
|
COOH
C
H



 ; (C) ; (D)
Q.18 (D) ; (E) Q.19 (F)
Q.20 (A) CH3CH2NH– Q.21
EXERCISE - III
Q.6 (A)
acid
Succinic
COOH
CH
|
COOH
CH
2
2
(B) (C) (D)
COOH
CH
|
ClCOOH
CH
2
2
(E)
COOK
CH
|
COOK
)
OH
(
CH
2
2
(F)
maleate
Potassium
CHCOOK
|
|
CHCOOK
Q.7 (A) (CH3)2CHCONH2; (B) (CH3)2CHNH2 ; (C) (CH3)2CHOH ; (D) CH3COCH3
Q.8 (A) CH3CH2CH3CONH2; (B) CH3CH2CH2NH2; (C) CH3CH2CH2COONa; (D) CH3CH2CH2CN
(E) CH3CH2CH2COOH; (F) CH3CH2CH2OH ; (G) CH3CH2CHO; (H) CH3CH2COOH
Q.9 (A) (B) (C) (D)
Q.10 (A) CH3CH2CN ; (B) CH3CH2COOH; (C) CH3CH2CH2NH2; (D) CH3CH2CH2OH
Q.11 (A) CH3CH2CONH2; (B) C2H5CN; (C) C2H5COOH; (D) CH3CH2CH2NH2;
(E) CH3CH2CH2

N

C

Q.12 (A) 3
CH
C
|
|
O

; (B) OH
N
C
|
CH3

 ; (C) N
C
|
|
OH
CH3
 ;(D) 3
CH
C
NH
|
|
O


(E) 3
CH
NH
C
|
|
O


; (F) NH2 ; (G) OH
C
|
|
O

Q.13 (A) OH
N
C
|
CH3

 ; (B) 3
CH
C
NH
|
|
O

 ; (C) CH3COOH; (D) NH2
(E)


Cl
N2
Q.14 (A) COOH
CH
CH
CH
|
OH
2
3 

 ; (B) CH3–CH=CH–COOH
Q.15 (A) ; (B) Br–CH(COOEt)2; (C) ;
(D)
COOEt
|
COOEt
CCH
|
COOEt
2 ; (E)
COOEt
|
COOEt
CCH
N
H
|
COOEt
2
2
 ; (F)
Q.16 (A) CH2 = C(OH)–COOH; (B) CH3–C(NH2)–COOH; (C) CH3CH(OH)–COOH
Q.17 (A)
COOH
)
OH
(
CH
|
COOH
)
OH
(
CH
; (B) CH3–CO–COOH; (C) CH3–CH(OH)–COOH
Q.18 (A) CH3–CO–CH3; (B) (CH3)2C=CHCOCH3; (C) (CH3)2C=CHCOOH; (D) (CH3)2C=CH2
Q.19 (A)CH3–CO–CH3; (B) (CH3)2C(OH)CN; (C) (CH3)2C(OH)COOH; (D) CH2= C–(CH3)–COOH
(E) CH3–CH=CH2
Q.20 Claisen condensation, (A) C2H5COOC2H5; (B) C2H5COCH(CH3)COOC2H5;
(C) C2H5COCH(H3)COOH
Q.21 (A) CH3CH(OH)CH2COOH; (B) CH3CH=CHCOOH; (C) CH3CH=CHCOCl
(D) CH3–CH=CHCON(CH3)2; (E) CH3COCH2COOH; (F) CH3COCH3; (G) CH3CH2CH3
Q.22 (A) CH3–CO–CH2CH2–COOH; (B) CH3COCH2CH3; (C) CH3C(OH)(CN)CH2CH3
(D) CH3C(Cl)(CN)CH2CH3; (E) CH3C(CN)2CH2CH3; (F) CH3C(COONa)2CH2CH3
Q.23 (A) ; (B) ; (C) ; (D) ;
(E) ; (F)

EXERCISE - IV (A)
Q.1 A,B Q.2 A Q.3 B Q.4 D Q.5 C Q.6 C Q.7 D
Q.8 A Q.9 C
EXERCISE - IV (B)
Q.1 (A) CH3CH2CH2COOCH2CH3; (B) CH3CH2OH ; (C) CH3CH2CH2CH2OH; (D) CH3CHO;
(E) CH3CH= CHCHO
Q.2 (A) SOCl2; (B) POCl3; (C) CH3COCl; (D) CH3COCH3
Q.3 (i) (A) CH3CHBrCOOH; (B) CH2 = CHCOOH;
(ii) (A) CH3CH(OH)CH2COOH; (B) CH3COCH2COOH
Q.4 (A) (CH3CH3CO)2O; (B) CF3CH2COOH; (C) CH3CH2COOH; (D) (CF3CH2CO)2O
Q.5 (A) NaCH(COC2H5)2; (B) 5
2
3
2
5
2
H
COOC
HC
CH
|
)
H
COOC
(
HC



Q.6 (A) CH3COOH; (B) C2H5O18H
Q.7 BaC*O3 + H2SO4  C*O2(X) + BaSO4
CH2=CH–Br





 

O
H
)
iii
(
O
*
C
)
ii
(
,
Mg
)
i
(
3
2
CH2=CH–C*OOH(Y) 

 
 4
LiAlH
CH2=CHC*H2OH(Z) 


H
CH2=H–C* 
2
H C* 
2
H CH=C*H2
 Br–  Br–
CH2=CH–C*H2 Br BrCH2 – CH=C*H2
O3ZnH2O  O3ZnH2O Br–C*H2CHO + HCHO Br–CH2CHO + HC*HO
Q.8
H
|
COOH
C
CH
|
Ph
3 
 +
Ph
|
COOH
C
CH
|
H
3 










 

,
SO
H
.
conc
CH
|
OH
C
CH
CH
)
(
|
H
4
2
3
2
3
(racemic mixture)
3
3
2
3
CH
O
H
|
|
|
|
CH
CH
C
O
C
C
CH
|
|
H
Ph




 +
3
3
2
3
CH
O
Ph
|
|
|
|
CH
CH
C
O
C
C
CH
|
|
H
H





during esterification reaction only –COOH and –OH partcipates. There is no effect on structure or
configuration ofcarbon adjacent to these groups. So when(±) acid reacts with pure (+) alcohol two
esters are produced which are diastereoisomers ofeach other.
Q.9 (A) (B) (C) (D)