CLASSROOM CONTACT PROGRAMME

DPP - 6
BENGALURU, KARNATAKA (Academic Session : 2020 - 2021)

JEE (MAIN + ADVANCED) : ENTHUSIAST COURSE

TARGET: JEE (M + A) 2021
TOPIC : HYDROCARBON WORKSHEET - 6
Paragraph for Q.1 to Q. 2
Among the following alkenes :

Me
Me
Me Me

Me
Me

(I) (II) (III) (IV) (V)

Me Me
Me Me
Me Me

Me
Me Me Me

(VI) (VII) (VIII) (IX)

Me

Me
(X)

1. From the following options identify alkenes which give single optically active ozonolysis product
in presence of Zn.
(A) (V) (B) (I) (C) (III) (D) (VI)
Ans (A)
2. From the following options identify alkenes which give meso product on ozonolysis in presence
of Zn.
(A) (III) (B) (IX) (C) (X) (D) (VII)
Ans (A)
3. How many of the following will give ketone as product ?
H2C=CH2 ¾¾¾¾ ¾® (ii) CH3–CH=CH2 ¾¾¾¾ ¾®
(i)O3 (i)O3
(i) (ii) Zn / H2O (ii) Zn / H2O

CH3
(iii) CH3 – C = CH2 (iv)

(v) (vi)
H
CDG/02CM114002
(vii) H2C=CH–CH2–CH=CH–CH3 ¾¾¾¾ ¾®
(i)O3
(ii) Zn / H2O

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BENGALURU, KARNATAKA DPP - 6
(A) 3 (B) 4 (C) 5 (D) 6
Ans (C)
4. How many of the following reactants show Gl ?
H
(i)O3
(i) X ¾¾¾¾¾
(ii) Zn / H2O
® CH3 – CH2 – C – H (ii) X O + O
O H

H O O
(iii) X O + O (iv) X +
H H

(v) X O

O
H3C H
(vi) X + C=O + C=O
H3C H
O

O
(vii) X
O
(A) 3 (B) 4 (C) 5 (D) 6
Ans (D)
5. Which of the following compounds can give a mixture of diastereomers on treatment
of H2/Pt ?

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

Ans. (A,B)
6. Select option(s) in which incorrect major product is shown:
co nc.H 3 PO 4
(A) D
OH

(B) D + AcOH
OAc
–
OH
(C) Ph –CH2 –CH –CH3 D Ph –CH =CH –Me
NEt3
Me
H Br
B r2
(D) C C l4 H Br
Me CDG/02CM114002

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 BENGALURU, KARNATAKA DPP - 6
Ans. (A,B,D)
7. Match the column -
Column - I (Organic reactions) Column - II (Type of reaction)
D
D
(A) O2N & O2N both compound (P) E1 reaction
F F

give same rate of reaction with Alcoholic KOH

Cl Cl
(B) & give different rate with Alcohol KOH/D (Q) E2 reaction
CD3 CD3
CD3

OH OH
(C) & give different rate with conc. KHSO4/D (R) E1CB reaction

Me
Cl
MeOH
(D) P (S) Bimolecular reaction
Me

(T) Uni molecular reaction

Ans. (A) -R,T ; (B)-Q,S ; (C)- P,T ; (D) T
8. Correct order is / are :
(A) CH2=CH2 > HCºCH (Reaction with O3)
(B) CH2=CH2 > HCºCH (Reaction with HBr)
(C) CH2=CH2 < HCºCH (Reaction with H2/Ni)
(D) R–C–OH > R–C–R (Reaction with BH3/THF)
|| ||
O O
Ans. (A,B,C,D)

(1) BH3/THF
9. Possible products -
(2) H2O2/OH–

HO HO O

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

OH

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BENGALURU, KARNATAKA DPP - 6
Ans. (A,B,C)
Paragraph for Q.10 to 11
Among the following alkenes :

Me
Me Me
(1) (2) (3) (4)
Me

Me Me Me
Me
Me Me
(5) (6) (7) (8)
Me
Me Me Me Me

Me Me

(9) (10)
Me
10. From the following options identify alkenes which give single optically active ozonolysis product
in presence of Zn :-
(A) 4 (B) 1 (C) 3 (D) 6
Ans (A)
11. From the following options identify alkenes which give meso product on ozonolysis in
presence of Zn :-
(A) 3 (B) 9 (C) 10 (D) 7
Ans (A)
12. In which of the following reaction the resolvable products is / are obtained
(1) H /Pd-BaSO 4 (1) Li / N H 3
(A) CH3—C C—CH3 (2) Br2 /CCl (B) C2H5—C C—C2H5 (2) Br /CCl
2 4 2 4

O
(1) H 2/Pd-BaSO 4
(C) CH3—C C—CH3 (D) CH3—CH HCN
(2) dil. KMnO 4

Ans. (A,D)
13. A polyene (A) reacts with 3 mole of H2 gas in presence of platinum catalyst to form 1-isopropoyl
4-methyl cyclohexane. When (A) undergoes ozonolysis, following products are obtained

O O O O O O
|| || || || || ||
H–C–H , H–C–CH2–C–C–CH3 , CH3–C–CH2–C–H

(A) is :

CDG/02CM114002

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

Ans. (B)

14. H 3C n o p ero xide Product is:

CH2 + HBr

(A) Br Br
(B) H3C
Br
H3C H3C

Br
(C) H3C (D) H3C Br

H3C

Ans. (C)
15. Markownikoff's rule is not applicable on which of the following alkene :

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

Ans. (C)
16. Major product in following reaction is/are :
Br2
CCl4

Br H Me
Me Me
H Me Me H Br
(A) (B) (C) Br (D)
Br H
H Br H
Br Br
Br Me
Ans. (A,B)
17. Column - I Column - II
(Reaction) (Statements)

H3C CH3 Br2

(A) C=C H2O (P) Product mixture is racemic
H H

H3C H Br2
(B) C=C CCl4 (Q) Product is meso
H CH3

H3C (i) Hg(OAc)2 / H 2O

(C) C–CH=CH2 – (R) Major product contains 2º alcohol
H (ii) NaBH 4 , OH
 BENGALURU, KARNATAKA DPP - 6

H3 C (i) BH3-THF
(D) CH=CH2 – (S) Hydrocarbon reactant has lowest HOC
H3 C (ii) H2O2, OH

(T) Major product contains 1º alcohol

Ans. (A) ® P, R ; (B) ® Q ; (C) ® P, R ; (D) ® S,T

Ph Ph
OH
Conc. H2SO4
18. 180º C
Alkene
(Major product)

Number of transition states formed during the above reaction is/are :

Ans. (6)
19. Column - I Column - II
(Reactions) (Statements)
OH H
+

(A) (P) Major product is Saytzeff alkene

CH2–CH=CH
(B) HBr (Q) Major product is Hoffmann alkene

Conc. H2SO4
(C) (R) Rearragement takes place
OH
2+
Hg /dil.H 2SO 4
(D) Ph–C CH (S) Markovnikov's addition takes place

(T) Carbocation (classical or non-classical) is formed

as an intermediate

Ans. (A) ® P, R, T ; (B) ® R, S, T ; (C) ® Q, T ; (D) ® S,T

OH Conc.H2SO 4
20.

Total number of 1,2-shift involve in above reaction :

Ans. (3)

Br2
21. Reaction (I)
(CCl4)
X
Br2
Reaction (II)
(CCl4)
Y

Correct option :

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 (A) X on treatment with Br2(CCl4) give optically active product
(B) Y on treatment with Br2(CCl4) give optically active mixture of products
(C) Reaction (I) & Reaction (II) giving different nonclassical carbocation intermediate
(D) Product formed in reaction (I) is enantiomer of one of product formed in reaction (II)
Ans. (C)
22. Which compound decolorises Br2/ HOH solution ?
CH=CH–CH3 CH3
(A) (B) (C) (D) HCºCH

Ans. (B,C,D)
23. Identify reactions correctly matched with their major products ?
(1) BH3–THF +
(A) – Me Me
(2) H2O2 + OH
H OH H OH
O
(1) B2H6
(B) Me— C CH – Me—C—CH3
(2) H2O2 / OH

O
1 % HgSO4
(C) Me— C CH
Dil. H2SO4

O
OH (1) Hg (OAc)2 /H2O
(D) (2) NaBH4 / OH
–

Ans. (A,C,D)
O
H gSO
24. 1-butyne + 1 % H S4O X m issin g rea g en t C H 3C H 2 – C – C l
2 4

The missing reagent can be :

(A) (CH3)2Cd (B) DIBALH (C) H2 (Lindlar catalyst) (D) EtMgBr
Ans. (A)
25. CH3 – C C – CH2 – CH 3
O3 + H2O

Product is :
(A) Mixuture of ethanal & propanal (B) Mixture of methanoic & propanoic acid
(C) Mixture of ethanoic acid & propanoic acid (D) Mixture of ethanoic acid & propanal
Ans. (C)
BENGALURU, KARNATAKA DPP - 6

HBr + H2O2
26. Product. , Product is :

(A) 3º alkyl bromide (B) 1º alkyl bromide (C) 2º alkyl bromide (D) 1º alcohol
Ans. (B)
27. Major product and type of product in following reaction is :

Cl
H Alc. KOH

(A) , Saytzeff (B) , Saytzeff

(C) , Hoffmann (D) , Hoffmann

Ans. (D)
28. Which of the following compound(s) will give same major product when treated with HBr :

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

Ans. (A,B,D)
29. Reaction(s) incorrectly matched with its major product is/are :
HCl
NBS
(A) Ph Ph (B) Br
Cl

Cl
HCl
Cl
(C) O2N O 2N (D) HCl

Ans. (A,C,D)
30. Reaction(s) incorrectly matched with its major product is/are :
+
HBr H3O
(A) (B)
OH
Br

HBr HBr
(C) ROOR Br (D) (1 eq.) Br
Ans. (A,D)

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 DPP - 6_ANSWER KEY
Q. No. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans. A A 3 4 AB ABD * ABCD ABC A A AD B C C
Q. No. 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Ans. AB * 6 * 3 C BCD ACD A C B D ABD ACD AD
7 (A) -R,T ; (B)-Q,S ; (C)- P,T ; (D) T
17 (A) - P, R ; (B)- Q ; (C)- P, R ; (D) - S,T
19 (A) - P, R, T ; (B) - R, S, T ; (C)- Q, T ; (D) - S,T