Page # 108 Solutions Slot – 3 (Chemistry)

Exercise - II (Only one option is correct)

Sol.1 A Sol.8 C

–C– + Nu O O

O ClC CCl
Acyl carbon shows addition elimination + CH 3 CH 2 CH 2 CH 2 NH 2
mechanism by attack of Nucleophilic.
Br S Br
Sol.2 B 140ºC

Sol.3 C
Primary amines, secondary amines and O O
ammonia all react rapidly with acid chlo-
rides to form amides, This reaction takes CH3–(CH2)3–NH–C C–NH–(CH2)3–CH3
place at room temperature and gives high
yield.
Sol.4 A Br S Br

C6H5
C6H5CO2H SOCl2 C6H5COCl AlCl C6H5COC6H5 N–(CH2)3–CH3
3

Sol.5 D O
O
O O O C C
NaOH + NH3
C–Cl + NH2–NH2 C–NH–NH–C
–HCl

Br S Br
Sol.6 D
2 mole  EtO–CO–OEt Sol.9 D
4 mole NH4  NH2–CO–NH2+NH4+Cl
NH2 O
O O
NH3
C + 1 C 2H 5 OH C + Cl – C – Cl
Cl Cl C2H5O NH2 CO2H

Sol.7 C NH O
C
O O
C O + 2 mole of HCl
CH3O C Cl+ C CH
O
OH
Sol.10 B
Pyridine
O
O O (i) Li AlH 4
(CH3)3 C–C–Cl +
(CH3)3C–CH2–OH
+ HCl (ii) H3 O
CH3–O C–O–CH–C
(i) [(CH3)3CH2]4 AlLi
(ii) 4(CH3)CCH2OH

Sol.11 C
O
CH3–(CH2)4–C–Cl + (CH2=CH)2CuLi

CH3–(CH2)4–C–CH=CH2

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 Solutions Slot – 3 (Chemistry) Page # 109
Sol.12 B
O O Sol.18 C
O
PhCH2–C–Cl+CH3CH2SH Ph–C–S–CH 2–CH3+ EtOH, H 2SO4
HCl R–COOH R–C–OEt (esterifica-
tion)
Sol.13 A Thus X is (C)
O
Sol.19 D
(I) Only Resonance
CH 3– C – O – C6H5 OC2H5
OCH3 H/H 2O

O COOC 2H5
(II) CH3– C – O – no Resonance
OH
OH + 2C 2H 5–OH + CH3OH
O
(III) CH3– C – O – CH3 Resonance + COOH

+I effect of CH3 –H 2O
O
(IV) CH 3– C – O – Cl Resonance + –I ef- O

fect of Cl
COOH

Sol.14 B Sol.20 C
–M effect (–CHO) < –M effect (–NO2) O
CH2COOC2H5 CH2–C
Sol.15 A H O +C2H5–OH
O CH2OH CH2
CH3–C–O–R
Reactivity order of saponification of es- Sol.21 C
ters O O
1°R>2ºR>3°R H
+ R"–OH + R'–OH
C C
R O–R' R O–R"
Sol.16 A
O
(I) NO2 COOC2H5 is more reac-
C
tive because of –M effect of –NO2 Thus, X = 2 O O

O CH2 CH2
(II) NO2 O–C–CH3 is more re- Sol.22 A
active O
because of –M effect of –NO2 > –M effect (– O
OCH3) O —
OCH3
(III) 6 member ring is less reactive to 4 CH3O–C–(CH2) 5–O
CH3OH
member ring.
H

Sol.17 B O
O CH3O–C–(CH2)5–OH
CH3OH + R COOH  CH 3OCR
Reactivity order of esterification
H > 1°R > 2° R > 3° R

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 Page # 110 Solutions Slot – 3 (Chemistry)

Sol.23 B
Sol.29 A
(i)LiAlH4
O O R–C–NH 2 R–NH2
— (ii)H2O
EtO
Et–C– O O Reduction
EtOH
O
Sol.30 B
H I  no resonance
II  –I effect
HO COOEt III  – M effect
IV  Resonance

Sol.31 A
Sol.24 B
Ease of esterification for alcohols  more O O
acidic alcohols ONa
N–H NH 2
Sol.25 A H2O
COOH
H3O+ COOH O O
O COOH O + 3CO 2
COOH
RC–NH2 RCONa+NH3
COOH H 2O
Sol.32 A
Sol.26 D KOBr
(CH3)3–C–COOH (CH3)3–C–NH2 (CH3)3–C–OBr
O OCH3
HO HNO2
C–CH3 C–CH3
CH3OH/ H (CH3)3C–OH
1.eq
C–OH C–OCH3
Sol.33 C
O O
CH3 O
PhCH2–CH–CH2–C–NH 2
CH3O CH 3
C Br2,NaOH
CH3
O + CH3OH
C PhCH2–CH–CH2–NH2+Na2CO3+NaBr+H2 O

O Sol.34 A
O O
Sol.27 C 15
O O C–NH2 + CH2–C–NH2
CH3NH2
C–OCH 3 C–NHCH3 + CH3OH

Sol.28 C
15
COOH CONH2 NH2
KMnO4/OH NH3 CH2–NH2
COOH CONH2
+

O
OH/Br2
C RCNH2 RNH2
NH + NH3
C
O

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 Solutions Slot – 3 (Chemistry) Page # 111
Sol.35 C Thus X=(A)
O
hot dil. NaOH Sol.40 B
H2N–C–NH2 Na2CO3+NH3 O O

LiAlH4 OH
Sol.36 B O
NH2
OH
C2H5 COOH C2H5 COCl O=C C 2H5 CO – NH
SOCl2 NH2 C C O +2HCl
C C O O
C2H5 C2H5 C 2H5ONa C 2H5 CO – NH
COOH COCl
PCC
Sol.37 A O
COOH COOH
N H
NH2–NH2
N
[A] CH2 H
CO2 CH3
COOH O
Sol.41 B
Sol.38 C O O

O C C OCH3
CH3
CH–COOH CH3 O + CH3OH
CH–C
C C OH
O
H2C –H2O O O
COOH CH2 C
O
Sol.39 A
O O O O
R COC R + R'NH2 R C NHr' + HOCR

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