 Reduction 1

REDUCING AGENTS AND THEIR ROLE

Group Product LAH in NaBH4 B2H6 H2 /

Ether in H2O in THF Catalyst 

–CHO –CH2OH + + + +

>C = O >CH – OH + + + +

–CO2H –CH2OH + – + –

–CO2R –CH2OH + – + +

–COCl –CH2OH + + – +

–CONH2 –CH2NH2 + – + +

(RCO)2O RCH2OH + – + +

–CN –CH2NH2 + – + +

>C = NOH –CH2NH2 + – – +

>C = C< >CH – CH< – – + +

–C  C– –CH = CH– – – + +

1° RX RH + – – +

Note :
node06\B0B0-BA\Kota\JEE(Advanced)\Leader\Che\Sheet\Reduction\Eng.p65

1. B2H6 in THF not able to reduce cyclic ester.

2. NaBH4 can also reduce imine group ( C = NH ).

3. Reactivity order towards Ni / H2 ,  –C  N > –C – O – R

O

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2 JEE-Chemistry 

Name Reagent Function

H
Wolf Kishner Reduction (i) N2H4 / (ii) KOH, O
H
H
Clemenson Reduction Zn–Hg / HCl O
H
SH H
Mozingo Reduction Dry HCl, followed
O
by Raney Ni
SH H
SnCl2 / HCl followed
Stephen's Reduction + R–C N R–CH=O
by H3O
CH3 CH3
MPV Reduction Al –O–CH HO–CH O OH
CH3 3 CH3

C=C C—C
H H
Hydroboration Reduction B2H6 / AcOH, H2O
O O
H H

Bouvoult Blank Reduction Na / EtOH R–COO–R RCH2OH +ROH

Transfer Hydrogenation N2H4 / H2O2 C=C C—C

H H
O O

H2, Pd–BaSO4 R—C—Cl R—C—H

Rosenmund Reduction
* —C C— —C C—
H H
H
Birch Reduction Na / Liq. NH3 —C C— —C C—
H
—COOR
H–Al –CH2–CH–CH3 —C N
—COCl —CHO
node06\B0B0-BA\Kota\JEE(Advanced)\Leader\Che\Sheet\Reduction\Eng.p65

CH3 2
DIBAL-H O O
(–78°C) followed by H3O+ —C–O–C–

—CHO —CH2OH

R–CO2H RCH3
R–CH=O RCH3
Red phosphorus in R–C–R RCH2R
presence of HI Red P + HI
O
R–OH R–H

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  Reduction 3

EXERCISE # O-I
SH
HS H 2 / Ni
1. O  
The end products of the reaction are :
(A) SH and SH
(B) S–CH2–CH2–SH
S
(C) and H2O
S
SH
(D) and HS
RD0001
CH2
H ,Pd
2. 2 

CH3
Products of the above reaction will be :
(A) Racemic mixture (B) Diastereomers (C) Meso (D) Structural isomer
RD0002
D
NH 2  NH 2
3. 
H2 O2
 Product :
D
D D
H H
(A) (B) (C) (D) Both (B) and (C)
D H
H D
RD0003
4. On catalytic reduction with H2/Pt how many alkenes will give n-butane ?
(A) 1 (B) 2 (C) 3 (D) 4
RD0004
H3C D
H / Ni
5. C=C 2

D CH3
Product of above reaction will be :
(A) Racemic mixture (B) Diastereomers (C) Meso (D) Constitutional isomers
RD0005
H3C CH3
node06\B0B0-BA\Kota\JEE(Advanced)\Leader\Che\Sheet\Reduction\Eng.p65

H 2 / Ni
6. C=C  
D D
Product of above reaction will be :
(A) Racemic mixture (B) Diastereomers (C) Meso (D) Constitutional isomers
RD0006

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4 JEE-Chemistry 
O O
CC
7.

Which reagent will be used for the above conversion ?

(A) Na/Liq. NH3 (B) H2, Pd–CaCO3 (C) Li, Ph–NH2 (D) H2, Pt
RD0007
COOH

Li
8. 
Liq .NH3
 Major product :

COOH COOH COOH CH2OH

(A) (B) (C) (D)

RD0008
OCH3

Na,Liq,NH 3
9.    Major product :

OCH3 OCH3 OCH3

(A) (B) (C) (D) None of these

RD0009
Conc.H 2SO 4 Pt / H 2
10.  
 A   B

A and B respectively are :

(A) Both (B) ,

(C) , (D) ,
RD0010
11. If the following compound is treated with Pd in excess of H2 gas, how many stereoisomers of the product
will be obtained ?
node06\B0B0-BA\Kota\JEE(Advanced)\Leader\Che\Sheet\Reduction\Eng.p65

(A) 1 (B) 2 (C) 3 (D) 4

RD0011

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  Reduction 5
H2C CH2
H 2 ,Ni
12. C—C   Product :
1 eq .
D D
H3C CH2 H3C D
(A) C—C (B) C=C
H D CH3
D D
H3C CH3
(C) C=C (D) All of these
D D
RD0012
13. Which alkyne gives 3-ethylhexane on catalytic hydrogenation ?

(A) (B) (C) (D) All of these

RD0013
O
O O NaBH 4
14.   Product
O
O Cl
The product is :
O
(A) HO OH (B) CH3–CH2–OH

OH
O
OH
O O
(C) HO OH (D)
O
OH
OH RD0014
AgCN H 2 , Ni
15. Br A B
The final product (B) is :
H
NH2 N
(A) (B) N (C) (D) NH2
H
RD0015
node06\B0B0-BA\Kota\JEE(Advanced)\Leader\Che\Sheet\Reduction\Eng.p65

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6 JEE-Chemistry 
EXERCISE # O-II
1. Column-I Column-II
(Conversion) (Required Reagent)
H3C CH3
(A) H3C–CC–CH3  C=C (P) H2 , Pd-BaSO4
H H
H3C H
(B) H3C–CC–CH3  C=C (Q) Li , Liq.NH3
H CH3
(C) H3C–CH=CH–CH3  H3C–CH2–CH2–CH3 (R) N2H4 / H2O2 (1 eq.)
CH3 CH3

(D)  (S) B2H6 , CH3COOH

RD0016
O
?
2. R–C–R   R–CH2–R
Identify numbers of reagent that can be used for above conversion.
 CH2–SH
(a) Zn–Hg / HCl (b) LiAlH4 (c) N2H4 / OH (d) , H2 / Ni
CH2–SH
RD0017
3. Column-I Column-II
(Conversion) (Required Reagent)
O
||
 –CH2OH
(A) –C–OH  (P) LiAlH4
O
||
(B) –C–Cl 
 –CH2OH (Q) NaBH4
O
||
(C) –C–OR' 
 –CH2OH (R) B2H6 / THF
O
||
R–C
(D)  R–CH2OH
O  (S) H2 / Catalyst, 
R–C
||
O
RD0018
node06\B0B0-BA\Kota\JEE(Advanced)\Leader\Che\Sheet\Reduction\Eng.p65

4. How many alkene on catalytic reduction gives following product.

(i) (A) H
2 / Pt
 n-butane (ii) (B) H
2 / Pt
 Iso-pentane
(iii) (C) H
2 / Pt
 Neo-pentane (iv) (D) H
2 / Pt
 Cyclopentane

H2
(v) (E) 
Pt
RD0019

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  Reduction 7
5. Give the expected major product for each reaction, including stereochemistry where applicable.
H2
(a) CH3–CH2–CH=CH2 
Pt
P1 RD0020

D2
(b) Pt P2 RD0021

H3C H
(c) C=C D
2
P RD0022
Ni 3
H CH3

Me
(d) Ni
/ H2  P4 RD0023
Me
H2/Pt
excess P5
(e) H2/Pt
RD0024
1 eq. P6
H2 / Pt
6. (i) CH2=CH–CH2–CH = O excess P1 RD0025
H2 / Pt
(ii) CH2=CH–CH2–CN excess P2 RD0026
7. (a) Identify the product ?
lH 4
LiA
NaBH4 D
(i)    Me–CHO –7IBAL- RD0027
8°C H

lH 4
LiA
NaBH4
(ii)    Me2CO DI
BA RD0028
L-H

lH 4
LiA
NaBH4
(iii)    Me–COCl DI
BA RD0029
L-H

lH 4
LiA
NaBH4
(iv)    Me–COOEt DI
BA RD0030
L-H

(b) Identify the product ?

node06\B0B0-BA\Kota\JEE(Advanced)\Leader\Che\Sheet\Reduction\Eng.p65

NaBH4 LiAlH4
(v)    Me–COOH    RD0031
NaBH4
(vi)    Me–COOMe LiAlH
 4  RD0031
NaBH4
(vii)    Me–CONH2 LiAlH
 4  RD0031
NaBH4 LiAlH4
(viii)    Me–CONH–Me    RD0032
NaBH4
(ix)    Me–CONMe2 LiAlH
 4  RD0032
NaBH4
(x)    CH3–CH = CH2 LiAlH
 4  RD0032

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8 JEE-Chemistry 
8. Give product in following reactions.
NaBH4 LiAlH4
(i)   O    RD0033

NaBH4 LiAlH4
(ii)    H–N O    RD0034

NaBH4 LiAlH4
(iii)   O    RD0033
N
H

(iv) LiAlH
 4  RD0034
N

NaBH4
(v)   O LiAlH
 4  RD0033
O
NaBH4 LiAlH4
(vi)   O    RD0034
O
O
NaBH4
(vii)    Me–CO–N LiAlH
 4  RD0033

NaBH4
(viii)   LiAlH
 4  RD0034
O
9. Give product in following reactions.
O COCH3
O
(a) Re d P  HI
H   (b) Red P + HI (c) Red P + HI
   
OH (excess) HO CH2OH (excess)
CHO
RD0035
10. Give product in following reactions.

(i) LAH
 RD0036
N O
node06\B0B0-BA\Kota\JEE(Advanced)\Leader\Che\Sheet\Reduction\Eng.p65

(ii) RD0037

LAH
(iii) CH–3 CH – CH 2 RD0038
O
LAH
AlCl3

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  Reduction 9

(iv) RD0039
O

11. Give product in following reactions.

CHO

NaBH4
(i) O RD0040
COOEt

O (i) LiAlH4
(ii) D2O
(ii) RD0041
(i) LiAlH4
(ii) H2O

O=C—CH3
12. (a) Zn )  (A) NBS
( Hg
  (B) alc
 .
(C) HCl
 (D)
HCl KOH R 2O 2

RD0042
O

13. (a) Zn

( Hg
) 
 RD0043
HCl , 

O
|| Zn ( Hg )
(b) Ph  C  CH3    RD0043
HCl

(c) Zn
( Hg
) 
 RD0043
HCl , H 2 O

O
(d) (
i ) H 2 NNH 2
  RD0044
(ii ) KOH ,heat

N2H4
KOH, heat
O O (excess)
Zn(Hg)
(e) O RD0045
node06\B0B0-BA\Kota\JEE(Advanced)\Leader\Che\Sheet\Reduction\Eng.p65

HCl
(excess)

DiBAL H DiBAL  H
14. (a) C – OH   (b) C  N 
–78C


O
DiBAL  H
(c) CH 3 – C – O – CH 2 – CH 3 
–78C

O
RD0046

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10 JEE-Chemistry 

O OH
?
15.
NO 2 NO2
above conversion can be achieved by
(A) LiAlH4 (B) H2 / Ni,  (C) NaBH4 (D) All
RD0047

node06\B0B0-BA\Kota\JEE(Advanced)\Leader\Che\Sheet\Reduction\Eng.p65

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  Reduction 11

EXERCISE # (MAIN & ADVANCE)

1. Hydrogenation of benzoyl chloride in the presence of Pd and BaSO4 gives : [IIT 1992]
(A) Benzyl alcohol (B) Benzaldehyde (C) Benzoic acid (D) Phenol
RD0048
2. Draw the stereochemical structure of the product in the following reactions. [IIT 1994]
H2
R–CC–R 
Lindlar catalyst

RD0049
3. Under Wolff Kishner reduction conditions, the conversions which may be brought about is?
(A) Benzaldehyde into Benzyl alcohol
(B) Cyclohexanol into Cyclohexane
(C) Cyclohexanone into Cyclohexanol
(D) Benzophenone into Diphenylmethane [IIT 1995]
RD0050
4. Which one of the following alkenes will react fastest with H2 under catalytic hydrogenation condition
[IIT 2000]

(A) (B) (C) (D)

RD0051
5. The appropriate reagent for the following transformation: [IIT-2000]
O
CH2 CH3
CH3 
HO HO

(A) Zn(Hg), HCl (B) NH2NH2, OH– (C) H2/Ni (D) NaBH4
RD0052
Me Me
H

6. H
Me
H
Hydrogenation of the above compound in the presence of poisoned paladium catalyst gives-
(A) An optically active compound (B) An optically inactive compound [IIT-2001]
(C) A racemic mixture (D) A diastereomeric mixture
RD0053
node06\B0B0-BA\Kota\JEE(Advanced)\Leader\Che\Sheet\Reduction\Eng.p65

7. When CH2 = CH–COOH is reduced with LiAlH4, the compound obtained will be -[AIEEE-2003]
(A) CH3–CH2–CH2OH (B) CH3–CH2–CHO
(C) CH3–CH2–COOH (D) CH2=CH–CH2OH
RD0054
8. 2–hexyne can be converted into trans–2–hexene by the action of : [IIT-2004]
(A) H2–Pd-BaSO4 (B) Li in liq. NH3 (C) H2–PtO2 (D) NaBH4
RD0055

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12 JEE-Chemistry 
Paragraph for Question No. 09 to 11
In the following reaction sequence, products I, J and L are formed. K represents a reagent.
1. Mg / ether
1. NaBH 4
Hex-3-ynal    I 2. CO 2 K
J  Me Cl H
2
L
  
2. PBr3 3. H O
3 || Pd/BaSO 4
quinoline
O
9. The structure of the product I is [JEE-2008]
Me
(A) Me Br (B)
Br
Me Br
(C) Me Br (D)
RD0056
10. The structures of compounds J and K, respectively, are [JEE-2008]
OH
(A) Me COOH and SOCl2 (B) Me || and SO2Cl2
O
(C) Me and SOCl2 (D) Me COOH and CH3SO2Cl
COOH
RD0056
11. The structure of product L is : [JEE-2008]

Me CHO
(A) (B) Me CHO

CHO
(C) (D) Me CHO
Me
RD0056
12. Consider all possible isomeric ketones including stereoisomers of MW = 100, All these isomers are
independently reacted with NaBH 4 (NOTE : stereoisomers are also reacted separately).
The total number of ketones that give a racemic product(s) is/are. [JEE-2014]
RD0057
13. In the reaction, [JEE-2014]
LiAlH PCl AlC. KOH
CH3COOH   A  4
 B  5
 C, Final product C is.
(A) Ethylene (B) Acetyl chloride (C) Acetaldehyde (D) Acetylene
node06\B0B0-BA\Kota\JEE(Advanced)\Leader\Che\Sheet\Reduction\Eng.p65

RD0058
14. The reagent needed for converting is : [JEE-2014]
Ph H
Ph–CC–Ph C=C
H Ph
(A) H2 / Lindlar Cat. (B) Cat. hydrogenation
(C) LiAlH4 (D) Li / NH3
RD0059

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  Reduction 13
15. The major product obtained in the following reaction is : [JEE MAIN-2017]
O
O

DIBAL-H

COOH
OH OH

CHO CHO CHO CHO

(A) (2) (3) (4)
COOH CHO COOH CHO
RD0060
16. Glucose on prolonged heating with HI gives : [Jee Main - 2018]
(1) 1–Hexene (2) Hexanoic acid (3) 6-iodohexanal (4) n-Hexane
RD0061
17. The trans-alkenes are formed by the reduction of alkynes with : [Jee Main - 2018]
(1) NaBH4 (2) Na/liq.NH3 (3) Sn–HCl (4) H2–Pd/C, BaSO4
RD0062
18. The main reduction product of the following compound with NaBH4 in methanol is :-
[Jee Main - Onl_line Morning 2018]
O O

NMe2

O O OH O

NMe2 NMe2
(1) (2)

OH OH O

NMe2 NMe2
(3) (4)

RD0063
19. The major product of following reaction is : [JEE-MAIN-On-line-(Jan)-2019]
(1)AlH(i–Bu 2 )
R – C  N (2)H 2O
  ?
node06\B0B0-BA\Kota\JEE(Advanced)\Leader\Che\Sheet\Reduction\Eng.p65

(1) RCHO (2) RCOOH (3) RCH2NH2 (4) RCONH2

RD0064
20. Wilkinson catalyst is : [JEE-MAIN-On-line-(Jan)-2019]
(1) [(Ph3P)3RhCl] (Et = C2H5) (2) [Et3P)3IrCl]
(3) [Et3P)3RhCl] (4) [Ph3P)3IrCl]
RD0065

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14 JEE-Chemistry 
21. The major product 'X' formed in the following reaction is :
[JEE-MAIN-On-line-(Jan)-2019]
O O
CH2–C–OCH3 NaBH 4

MeOH
X

OH O O OH OH O
CH2CH2OH CH2–C–H CH2CH2OH CH2–C–OCH3
(1) (2) (3) (4)

RD0066
22. The major product of the following recation is:
[JEE-MAIN-On-line-(Jan)-2019]
O
CH3N NaBH4
OH OH
(1) CH3N (2) CH3N
OH OH
(3) CH3N (4) CH3N
RD0067
23. The major product of the following reaction is:
[JEE-MAIN-On-line-(Jan)-2019]
O
OEt 
(i) Ni / H 2

(ii) DIBAL H
CN
H
O N NH OH
(1) (2) (3) (4)
CHO NH2
RD0068
24. The major product obtained in the following reaction is :-
[JEE-MAIN-On-line-(Jan)-2019]
O OH
Li AlH4
(excess)
CH3
node06\B0B0-BA\Kota\JEE(Advanced)\Leader\Che\Sheet\Reduction\Eng.p65

NO 2 O
O OH OH OH OH

(1) CH3 (2) CH3 (3) CH3 (4) CH3

NO 2 OH NH 2 OH NH 2 OH NO 2 OH
RD0069

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  Reduction 15

25. The major product of the following reaction is:

[JEE-MAIN-On-line-(Jan)-2019]
CN

(i) DIBAL-H
O +
(ii) H3O
O
CHO CHO CH=NH
CHO
(1) (2) O (3) OH (4) OH
O
OH
O CHO
RD0070
26. The increasing order of the reactivity of the following with LiAlH4 is :
[JEE-MAIN-On-line-(Jan)-2019]
O O
(A) C2H 5 NH2 (B) C2H5 OCH3

O O O
(C) C2H5 Cl (D) C 2H 5 O C2H5

(1) (A) < (B) < (D) < (C) (2) (A) < (B) < (C) < (D)
(3) (B) < (A) < (D) < (C) (4) (B) < (A) < (C) < (D)
RD0071
27. The major product of the following reaction is: [JEE-MAIN-On-line-(Jan)-2019]
O
NaBH

EtOH
4

OH
OH O OH
(1) (2) (3) (4)
OEt

RD0072
28. The major product of the following reaction is: [JEE-MAIN-On-line-(April)-2019]
O
Br
NaBH 4

node06\B0B0-BA\Kota\JEE(Advanced)\Leader\Che\Sheet\Reduction\Eng.p65

MeOH,25ºC

OH OH
OMe Br OMe O
(1) (2) (3) (4)

RD0073

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16 JEE-Chemistry 
29. The major product of the following reaction is : [JEE-MAIN-On-line-(April)-2019]
LiAlH 4
CH3 CH  CHCO2 CH 3  

(1) CH3CH2CH2CHO (2) CH3CH = CHCH2OH

(3) CH3CH2CH2CO2CH3 (4) CH3CH2CH2CH2OH
RD0074
30. The major products A and B for the following reactions are, respectively:

O
I KCN H2/Pd
[A] [B]
DMSO [JEE-MAIN-On-line-(April)-2019]

HO CN HO CH2–NH 2 O OH
I ; I CN ; CH2 –NH2
(1) (2)

HO CN HO CH2–NH 2 O O
I ; H CN ; CH2–NH2
(3) (4)

RD0075
31. What is the product of following reaction ? [JEE-MAIN-On-line-(Jan)-2020]
(i) NaBH4
Hex-3-ynal (ii) PBr ?
3
(iii) Mg/ether
+
(iv) CO2/H3O

(1) COOH (2) COOH

(3) COOH (4) COOH

RD0076
32. The most suitable reagent for the given conversion is : [JEE-MAIN-On-line-(Jan)-2020]
CH3
CONH2
C=O
?
node06\B0B0-BA\Kota\JEE(Advanced)\Leader\Che\Sheet\Reduction\Eng.p65

HO2C
CN

CONH2
COCH3

HOH2C
CN
(1) LiAlH4 (2) NaBH4 (3) H2/Pd (4) B2H6
RD0077
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  Reduction 17

ANSWER KEY
EXERCISE # O-I
1. Ans. (D) 2. Ans. (B) 3. Ans. (C) 4. Ans. (C) 5. Ans. (A)
6. Ans. (C) 7. Ans. (B) 8. Ans. (B) 9. Ans. (C) 10. Ans. (B)
11. Ans. (C) 12. Ans. (C) 13. Ans. (D) 14. Ans. (D) 15. Ans. (B)
EXERCISE # O-II
1. Ans. (A)P, R, S; (B)Q; (C)R, S; (D)Q 2. Ans. (3)
3. Ans. (A)P, R, S; (B)P, Q, S; (C)P, R, S; (D)P, R, S
4. Ans.
(i) Cis & trans 2-butene & 1-butene ; (ii) C–C –C=C C–C=C–C C–C–C–C
C C C
(iii) Zero (Neo-pentane can not be prepared by catalytic hydrogenation of alkene) ; (iv) One

(v) Including optical = 4 , Excluding optical = 3.

5. Ans.
D CH3 CH3
H D D H
(a) (b) (c)
D H H D
D CH3 CH3
CH3
H *
(d) (e)
CH3
H 2G.I.

6. Ans. (i) P1 = CH3–CH2–CH2–CH2–OH (ii) P2 = CH3–CH2–CH2 –CH2–NH2

8. Ans.

(i) OH , OH (ii) NH OH , NH OH

(iii) No reaction, (iv)

NH NH

(v) No reaction, CH2OH (vi) No reaction, CH2OH

OH OH

(vii) No reaction, Me–CH2–N (viii) ,

HO HO
node06\B0B0-BA\Kota\JEE(Advanced)\Leader\Che\Sheet\Reduction\Eng.p65

9. Ans. (a) (b) (c)

CH3

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18 JEE-Chemistry 
10. Ans.

OH
N OH CH OH
2

(i) (ii) (iii) CH3–CH–CH3, CH3–CH2–CH2OH

OH
OH

(iv)
CH2OH

CH2OH CHO CH2OH

LAH
NaBH4 +EtOH
11. Ans. (i) OH O OH
CH COOEt COOEt CH CH2OH
CH3 CH3

OD OH
H

(ii)

12. Ans.

O H
C–CH3 CH2–CH3 Br–C–CH3 CH=CH2 Cl–CH–CH3
Zn(Hg) NBS [Link] HCl
(a) HCl R2O2

13. (a) (b) Ph–CH2–CH3 (c) (d)

O O

(e) ,
node06\B0B0-BA\Kota\JEE(Advanced)\Leader\Che\Sheet\Reduction\Eng.p65

DiBAL H
14. (a) C – OH   C–H
O O

DiBAL  H C–H
(b) C  N 
–78C
 (c) CH3 – CHO
O
15. Ans.(C)

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  Reduction 19

EXERCISE # (MAIN & ADVANCE)

R R
1. Ans. (B) 2. Ans. C=C 3. Ans. (D) 4. Ans. (A)
H H
5. Ans. (B) 6. Ans. (B) 7. Ans. (D) 8. Ans. (B)
9. Ans. (D) 10. Ans. (A) 11. Ans. (C)
12. Ans. (5)
M. wt 100 of ketone
So m. formula = C6H12O

(1) n-Butyl –C–CH3 n-butyl CH–CH3

O OH
(2) Isobutyl –C–CH3 Isobutyl –CH–CH3 all are
O NaBH4 ± racemic mixture
OH
(3) 3º butyl –C–CH3 3ºbutyl–CH–CH3
O OH
CH3
(4) CH3–CH2–CH–C–CH3 CH3
CH3–CH2–CH–CH–CH3
O
R(2ºbutyl) OH
CH3 2-alcohols (R,R) & (R,S)
NaBH4 diastereomeric pair
(5) CH3–CH2–CH–C–CH3
O CH3–CH2–CH–CH–CH3
S(2ºbutyl)
CH3 OH
2-alcohols (S,S) & (S,R)
diastereomeric pair

(6) n-propyl –C–Et

n-propyl –CH–Et
O
OH (+)
– racemic
(7) Isopropyl –C–Et NaBH4 mixture

O Isopropyl CH–Et
(+) racemic
OH –
mixture
\ (1 ; 2 ; 3 ; 6 ; 7)
13. Ans. (A)
O
(A) (B) (C)
LiAlH4 alc KOH
CH3–C–OH CH3–CH2–OH PCl5 CH3CH2–Cl CH2=CH2
node06\B0B0-BA\Kota\JEE(Advanced)\Leader\Che\Sheet\Reduction\Eng.p65

Reduction of CH3 COOH will produce CH3–CH2 –OH(A)

Now reaction of CH3–CH2–OH(A) with PCl5 will produce CH3–CH2–Cl(B).
Now alcoholic KOH with Et–Cl will produce CH2=CH2(C) Ethylene by E2 elemination.
Thus Ans. is (1) Ethylene.
14. Ans. (D)
15. Ans. (1)

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20 JEE-Chemistry 
16. Ans. (4)
Sol. CHO
H OH
HO H HI/
H OH Reduction
n-Hexane
H OH
CH2OH
Glucose
17. Ans. (2)
Na/liq. NH3
Sol.

Birch reduction is anti addition. So trans alkene will be produced.

18. Ans. (4) 19. Ans. (1) 20. Ans. (1) 21. Ans. (4)
22. Ans.(3) 23. Ans. (2) 24. Ans. (2) 25. Ans. (3)
26. Ans. (1) 27. Ans. (4) 28. Ans. (4) 29. Ans. (2)
30. Ans. (2)
31. Ans. (3)
Sol.
O
NaBH4
CH3 – CH2 – C C – CH2 – C
H

CH3 – CH2 – C C – CH2 – CH2 – OH

PBr3

Mg/ether
CH3 – CH2 – C C – CH 2 – CH2 – Br

(1) CO2
CH3 – CH2 – C C – CH2 – CH2 – MgBr
(2) H 3O +
O
CH3 – CH2 – C C – CH2 – CH2 – C – OH
32. Ans. (4)
CONH2
C – CH3
Sol. O 

node06\B0B0-BA\Kota\JEE(Advanced)\Leader\Che\Sheet\Reduction\Eng.p65

HO 2C
CN
CONH2
COCH 3

HOH2C
CN
Most suitable reagent for given conversion is B2H6 (electrophilic reducing agent)