BATCH XII & DROPPER’S 2021 (ADV)

TOPIC REDOX REACTIONS IN

CARBONYL COMPOUNDS
DPP SUPER SIXER 16

Marking Scheme : Single Correct (+3,-1) M M: 96 Time : 1 hr

1. OH
; Compound A is
I2 + NaOH

OH
(Resorcinol) (holoform)

(a) (b)

(c) (d)

2. CO2 H ; Compound B is
(i) CH3 –Li (excess) I2
(ii) H A NaOH
B + CHI 3 

(a) (b) (c) (d)

3.
NaBH 4 LiAlH4
P ; Q

sum of number of 1° alcoholic groups in product P and Q is:

(a) 1 (b) 2 (c) 3 (d) 4

4.

Find missing reagents.

(a) x = LAH4, y = NaBH4 (b) x = LaH4 / AlCl3, y = LaH4
(c) x = LAH4, y = LAH4 / AlCl3 (d) x = H2 / Ni, y = H2 / Pt

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5. Which sequence of steps describes the best synthesis of 2-methyl-3 pentanone?

(a) (i) 1-propanol + (CH3)2CHMgBr, diethyl ether, (ii) H3O, (iii) PCC, CH2Cl2
(b) (i) 1-propanol + Na2Cr2O7, H2SO4, H2O heat, (ii) SOCl2, (iii) (CH3)2CHCl, AlCl3
(c) (i) 1-propanol + PCC, CH2Cl2 (ii) (CH3)2CHLi, diethyl ether, (iii) H3O, (iv) Na2Cr2O7, H2SO4,
H2O heat
(d) (i) 2-propanol + Na2Cr2O7, H2SO4, H2O heat, (ii) CH3CH2CH2Li, diethyl ether, (iii) H3O, (iv)
PCC, CH2Cl2
6. In which of the following group, each member gives positive iodoform test?
(a) methanol, ethanol, propanone (b) ethanol, isopropanal, methanal
(c) ethanol, ethanal, isopropyl alcohol (d) propanal, propanol-2 propanone
7. In the reaction OH OH ; product D is:
]

PCC OH OH MeMgBr NaBH 4, EtOH

A B C D
H H3O

OH OH OH
OH OH OH OH

(a) (b) (c) OH

(d)

8. Identify the reagents, required for the transformations shown and arrange them in correct order
Ph Ph Ph Ph Ph Ph OH OH Ph Ph Ph OH HO
Ph Ph OO H
[1 ] H [2 ] [3] [ 4] H Ph

HOH 2C CH 2OH
O O

(a) [1] LAH, [2] NaIO4, [3] NaBH4, [4] OsO4 (b) [1] OsO4, [2] NaIO4, [3] LAH, [4] NaBH4
(c) [1] OsO4, [2] LAH, [3] NaIO4, [4] NaBH4 (d) [1] LAH, [2] OsO4, [3] NaIO4, [4] NaBH4
9. OH ; product B is:
TsCl LiAlH 4
Pyridine
A B
Cl

(a) (b) (c) (d)

H OH
C
10. LiAlH 4
AlCl 3 A

H OH
C O
(a) No reaction (b) (c) (d)
Ph C Ph

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11. O find out the reactivity order with LiAlH4
O
RO C C
A
B
CHO
D
COCl
(a) A > B > C > D (b) B > C > D > A (c) D > C > B > A (d) B > D > C > A
12. Arrange the following compounds in order of their reactivity towards LiAlH4
O O O

(i) (ii) N
CH3
(iii) O

(a) (i) < (ii) < (iii) (b) (i) < (iii) < (ii) (c) (ii) < (i) < (iii) (d) (ii) < (iii) < (i)
OH
13. ; Compound C is:
H2SO 4 NBS LiAlD4
A B C
D OH

(a) (b) (c) (d)

14. Which of the following products is formed in good yield by the reduction of methyl 4-oxo-hexanoate
(A) with NaBH4?
O
O
Me
O
(a) Methyl 4-hydroxyhexanoate (b) 6-Hydroxy-3-hexaanone
(c) 1,4-Hexanediol (d) 4-Hydrodyhexanal
15. Which of the following pair is differentiated by iodoform test?
O O O O O
O O O
(a) , (b) , (c) , (d) , I
H H H Ph H C H CH2 I CH
I
16. What sequence of reactions would best accomplish the following conversion?
O O OH O
?
CH3 C Ch 2 C H CH3 CH Ch 2 C H
(a) NaBH4 / H3O (b) HOCH2CH2OH / H ; NaBH4; H  H2O
(c) KMnO4 / HO (d) LiAlH4 / H3O
17. O Cl O

N2H4 / KOH / H 2O
O (Wolff-Kishner reduction)
A
(major)

NO2
OH O Cl O Cl OH
O O
(a) O (b) O (c) (d)

NO2 NO2 NO2 NO2

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18. The given conversion can be achieved by:

(a) Wolff-Kishner reduction (b) Clemmensen reduction (c) LiAlH4 (d) NaBH4
19. Given conversion can be achieved by:

(a) Wolff-Kishner reduction (b) Clemmensen reduction

(c) HS–CH2–CH2–SH, following by Raney Ni (d) None of these
20. The given conversion can be achieved by:

(a) Wolff-Kishner reduction (b) Clemmensen reduction (c) LiAlH4 (d) NaBH4
21. O ; Identify product A and B from given product (p), (q) and (r).
C
(Hg
) A
Zn Cl
H
NH
2–
HO NH
/
B
2

OH
CH 2 CH3 CH 2 CH3 CH 2 CH3

(p) (q) (r)

OH Cl
(a) A–p, B–q (b) A–q, B–r (c) A–q, B–p (d) A–r, B–p
22. O ; Product A is
C CH3

N 2H4 / HO / 
(Wolff-Kishner reduction)
A

CH 2 CH2 Br

(a) (b) (c) (d)

CH 2 CH2 OH CH2 CH 2 OH CH CH 3
Br

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23. O This conversion can be achieved by:

O S O S

(a) Zn(Hg), HCl (b) NH2–NH2/KOH/ (c) LiAlH4 (d) H2 / Ni

O

24. HO C HO The shown reduction can be best carried out by:

(a) Clemmensen reduction (b) Wolff-Kishner reduction (c) NaBH4 (d) None of these
25. Which of the following gives yellow precipitate with NaOI?
OH O O
(a) I (b) Cl (c) Cl (d) All
Me Me Me
Cl
Cl
Me
26. A HI / P
Ph
LAH / ether
B The product A and B, respectively, are:
O
Me Me Me Me

(a) Me
and (b) and Me

( ) ( )
Ph Ph Ph Ph
OH OH OH OH
Me Me Me Me
Me Me
(c) Me and Ph
Me
+ (d) Ph
Me
+ and Me
Ph OH Ph OH OH Ph OH Ph
MnO2
A
27. OH
H 2CrO 4 + The product A and B, respectively, are:
aq. acetone B
OH (Jones reagent)

(a) O and O (b) O and O

O OH OH O

(c) OH and O (d) both O

O OH O
Me

28. ; The compound A is:

SeO2 / MeCOOH
100 – 140°C A
O
O OH OH O
Me Me O Me O Me
(a) (b) (c) (d)
O O O O

29.
SeO 2 / MeCOOH
100 – 140°C
A ; The compound A is:
O OH O OH

(a) (b) (c) OH

(d) OH

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30. Acid-catalysed hydration, oxymercuration-demercuration and hydroboration oxidation reaction will
give the same product with:
Me
(a) But-2-ene (b) But-1-ene (c) (d)

31. The increasing order of the rate of oxidation with HIO4 oxidation of the following is:
Me Me

OH OH Me OH OH
(i) (ii) (iii) (iv) Me
OH Me OH Me OH
OH
Me Me
(a) (iv) < (iii) < (ii) < (i) (b) (i) < (ii) < (iii) < (iv) (c) (iv) < (iii) = (ii) < (i) (d) (i) < (ii) = (iii) < (iv)
32. A
1 mol of CHO
; The compound A is:
HIO4 HOOC

OH O OH Me
(a) (b) (c) (d) OH
OH O O O

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All students are advised to solve DPPs within allowed time only.
All discussions are scheduled in every 4th doubt discussion class
–MKA Sir (Guruji)