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Batch Topic DPP
Batch Topic DPP
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
3.
NaBH 4 LiAlH4
P ; Q
4.
1
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:
]
OH OH OH
OH OH OH OH
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
H OH
C
10. LiAlH 4
AlCl 3 A
H OH
C O
(a) No reaction (b) (c) (d)
Ph C Ph
2
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
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)
3
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) 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
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
CH 2 CH2 OH CH2 CH 2 OH CH CH 3
Br
4
23. O This conversion can be achieved by:
O S O S
(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)
O OH OH O
O OH O
Me
29.
SeO 2 / MeCOOH
100 – 140°C
A ; The compound A is:
O OH O OH
5
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
6
All students are advised to solve DPPs within allowed time only.
All discussions are scheduled in every 4th doubt discussion class
–MKA Sir (Guruji)