CLASSROOM CONTACT PROGRAMMEDAY - 8

BENGALURU, KARNATAKA (Academic Session : 2020 - 2021)

JEE (MAIN + ADVANCED) : ENTHUSIAST COURSE

TARGET: JEE (M + A) 2021
TOPIC : HYDROCARBON WORKSHEET - 8
H CH3
C
1. C (cis form) ¾alkaline KMnO
¾ ¾ ¾ ¾¾4 ® A, which is true about this reaction?
H CH3

(A) A is meso 2, 3–butandiol formed by syn addition

(B) A is meso 2, 3–butandiol formed by anti addition

(C) A is a racemic mixture of d and l, 2,3–butandiol formed by anti addition

(D) A is a racemic mixture of d and l 2,3–butandiol formed by syn addition

Ans. A
CH3 CH3 OsO 4 Na 2SO 3
2. C=C ¾¾¾ ® I ¾¾¾¾
H2 O
® II
H H
The final product (II) of the reaction is :-
(A) meso-2, 3-butanediol (B) 2-butanol (C) (±) 2,3-butanediol (D) 2-butanone
Ans. A
3. Which of the following decolourises Bayer's reagent :-
CH 3

–
(A) CH3–CH 2–CH=O (B) CH3–CH 2–CH3 (C) (D) CH3–C=CH2

Ans. D

OS O4 Hot
4. (A) Kmno4 (B) ; A and B are :-

CH3 O CH3 CH3

OH OH
(A) , (B)
OH O OH OH

CH3 CH3 CH3

OH OH OH H
(C) (D)
OH O OH OH
Ans. C
Me

MCPBA / D
5. ¾¾¾¾
H 2 O / H+
® Major product :-

Me Me
Me Me

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

O O CDG/02CM114002
Ans. B

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BENGALURU, KARNATAKA DAY - 8
H - Br
CH3–CH=CH2 ¾¾¾ ® X ¾¾¾®
LiAlH 4
6. R 2 O2 Y; Y is :-

(A) CH3–CH 2–CH3 (B) CH 3–CH2–CH 2Li (C) CH 3–(CH2)4–CH 3 (D) (CH3)2CH–CH(CH3)2
Ans. A
(1) CO
® x ¾¾¾® y ¾¾¾
(2) H2O® z ; z is :-
Mg
7. CH2=CH–CH3 ¾¾¾
NBS
hv dryether
2

(A) CH2 = CH – CH2 – COOH (B) CH2 = CH – C – O – CH3

O O O

(C) CH2 = CH – C – O – C – CH 3 (D) CH2 = CH–CH2 –C–CH2–CH = CH2

Ans. A
CH3
CH3–C=CH–CH 3 ¾¾¾ ® , X (major) X is
NBS
8.

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

Br Br Br
Ans. C
9. Which gives only a single allylic bromide on heating with NBS :-
CH 3 CH3 CH3 CH3
(A) CH2=C–CH=CH 2 (B) CH3CH2–C=CH2 (C) CH2=CH–C–CH 3 (D) CH3–CH=C–CH 3
CH3
Ans. A
3 2 1 3 2 1
10. CCl3–CH=CH 2 CH3–CH=CH2
(I) (II)
In addition of HOBr to (I) and (II) :-
(A) Br is at C2 in both cases (B) Br is at C2 in II and at C1 in I
(C) Br is at C1 in II and C2 in I (D) Br is at in both cases
Ans. C
11. CH3CH = O
Identify best reagent sequence for above conversion ?
(A) (i) Cl2 / hv (ii) Alco.KOH /D (iii) O3/Zn
–
(B) (i) Cl2 / hv (ii) Alco. K+ O /D (iii) O3/Zn

(C) (i) NBS (ii) Alco.KOH /D

(D) (i) SOCl2 (ii) NaNH2 /D
Ans. A
12. Which of the following reaction does not involve cyclic reaction intermediate ?
(A) Hydroboration oxidation (B) Ozonolysis
(C) Addition of HOCl (D) Addition of HBr
Ans. D
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 BENGALURU, KARNATAKA DAY - 8
13. The order of reactivity towards HCl of the following compounds will be :-
H H CH3 H H H
(I) C=C (II) C=C (III) C=C
H H CH3 H CH3 CH3
(A) II > III > I (B) I > III > II (C) I > II > III (D) III > II > I
Ans. A
14. If butadiene is polymerised by a free radical synthesis the possible product contains which repeatation units ?

H2 C CH2 H2C H
(i) C C (ii) C C
H H n H CH2
n
(iii) CH2–CH2–CH2–CH n

(A) (i) & (ii) (B) (iii) only (C) (i) only (D) (i), (ii) & (iii)
Ans. A
OH
15. OsO4
¾¾¾ ® X + Y product (X) will be :-
80% 20%

OH OH OH
OH OH
(A) (B) (C) O (D) O
OH OH

Ans. A

16. Cold dil. KMnO4

¾¾¾¾¾¾ ® Product of the reaction :-

(A) Meso compound (B) Enantiomeric pair

(C) Diastereomers (D) Optically pure enantiomers
Ans. B
17. HBO, oxymercuration-demercuration and acid catalysed hydration will not give same product in

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

(A) a, b, c (B) b, c, d (C) a, b, d (D) a, c, d

Ans. C
18. Which alkyne gives 3-ethylhexane on catalytic hydrogenation ?

(A) 7 (B) (C) (D) All of these

Ans. D

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BENGALURU, KARNATAKA DAY - 8

OH
(i) Hg(OCOCH3)/HOH
19.
(ii) NaBH4
'A'
H2SO4
O3 / Zn
D + C C5H10
B
Major
alkene

Correct statement regarding above sequence of reaction.

(A) A give immediate turbidity with Lucasreagent
(B) Total possible isomer of B is 10
(C) Product C & D both give –ve Iodoform test
(D) Product C & D both form crystal with NaHSO3 (+ve NaHSO3 test)
Ans. D
20. Identify reagents give anti addition on alkene ?
(A) BH3–THF / H2O (B) OsO4 (C) 1 % KMnO4 (D) Br2 / CCl4
Ans. D
PhCO H H OÅ PI ,D
21. CH2 = CH2 ¾¾ ¾¾
3
® A ¾¾
3
¾® B ¾¾3¾® C
( 2 eq )

Structure of C is
(A) CH2 – CH2 (B) CH2 = CH2 (C) CH2 – CH2 (D) CH2 – CH2
OH I O I I
Ans. B
22. 2,2,6,6-tetramethyl cyclohexanol is treated with an acid. An alkene is formed. The structure of the
alkene is

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

Ans. A
O3+Zn
23. CH2= CH–CH2–CºCH H2O Products :-

(A) HCHO, O=CH–CH2–C–CH (B) HCOOH, O=CH–CH2–C–C–H

O O O O

O
(C) HCHO, HO–C–CH2–C–C–H (D) None
O O
Ans. A
24. The molecular formula of the first member of the family of alkenynes and its name is given by the set:-
(A) C 3 H2 , alkene (B) C5H 6, pent-1en-3-yne
(C) C6 H8 , hex-1-en-5-yne (D) C4 H4 , butenyne
Ans. D

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25. Products of the following reaction are
+
CH3 - C = CH - CH3 ¾¾¾¾¾
KMnO4 / H
¾
®
|
CH3

OH OH
| |
(A) CH3 - C -- CH - CH3 (B) CH3CHO+CH3CHO
|
CH3

(C) CH3COCH3 + CH3COOH (D) 2CH3COOH

Ans. C

26. ¾¾¾
HOCl
® I ¾¾¾¾
dil NaOH
® II ¾¾¾¾
dil H 2 SO 4
® III

The final product (III) is

(A) Epoxycyclohexane (B) 2-Chlorocylohexanol
(C) (+) Cis-1,2-cyclohexanediol (D) Trans-1,2-cyclohexanediol
Ans. D
27. Which of the following represent correct major product formation -
OH
dil.H2SO4
(A) CH3–CH–CH=CH2 CH3–CH–CH–CH3
CH3 CH3
OH
Hg(OAc).H 2O
(B) CH3–CH–CH=CH2 NaBH 4/OH
– CH3–C–CH2=CH3
CH3 CH3
B2H6
(C) CH3–CH–CH=CH2 NaOH/H 2O2
CH3–CH–CH 2–CH2–OH
CH3 CH3
OH
B2H6
(D) CH3–CH–CH=CH2 H2O/AcOH
CH3–CH–CH–CH3
CH3 CH3
Ans. C
28. Identify reactions correctly match with their major product .

Cl F
+ HCl + Alco.
(A) Me3N CCl4 Me3N (B) KOH /

Me
H Me NO
Br2
NOCl
(C) CCl4
H Br (D) CCl4
Br
Cl

Ans. D
BENGALURU, KARNATAKA DAY - 8
Paragraph for Q.No. 29 to 30

X
Alc.
+
KOH
Hoffmann's Satzaff's
product product

+ +
If 'X' is poor leaving group X = –F, –NR3 , –SR2 and strong base is used during reaction then
E2 – Elimination occur through partial anion formation and reaction/elimination favours from side
where alkyl substituents are less.
Mechanism

Ts1
H
OH
(Major product)
X
Alc. X
KOH
Ts2
H OH
(Minor product)

+ +
X = –F –NR3 –SR2

29.
Identify best reagent sequence for above conversion ?
(A) (i) H–F / CCl4 (ii) Alco.KOH /D (B) (i) NBS (ii) Alco.KOH /D
(C) (i) H–I / CCl4 (ii) Alco.KOH /D (D) (i) Br2 / CCl4 (ii) NaNH2 /D
Ans. A

N
+ Alcoholic
30. Major product (Alkene) ?
KOH /

N N N
(A) (B) (C) (D) CH2 = CH2

Ans. D

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