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Sheet-5-Hydro Carbon
Sheet-5-Hydro Carbon
SHEET – 5 – ALKENE
(Properties of Alkenes)
1. Which reagent is best to perform the following transformation?
H3C Ph
Cl2 ,CCl 4
2. C=C
H H
Ph Ph
H Cl
(A) H Cl (B)
Cl H H Cl
CH3 CH3
Ph
H Cl
(C) Ph C C CH 3 (D)
H CCl3
CH3
Br2 /CCl4
Major product:
OH
Br
Br
(A) (B)
Br
OH Br
Br
O
(C) (D)
O
Hg(OAc)2 ,H 2 O
4.
NaBD , OH
Major product:
4
(A) OH (B)
OH
(C) D (D)
OD
OH D
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Ph
Hg(OAc)2 ,CH3 OH
5. C = CH - CH3
NaBD , OH
Major product:
4
CH3
Cl 2 2NaNH2 H2 ,Pd-CaCO 3
6. Ph CH CH Ph
CCl 4
X Y Z
Identify product (Z) of the reaction.
Ph H Ph Ph
(A) C=C (B) C=C
H Ph H H
Ph
O3 / H2 O
(A) (B) HOOC — CH2 — COOH
(A) (B)
(C) (D)
H3C CH3
Br2 H2 O
8. C=C Product:
H H
CH3 CH3
H Br H Br
(A) (B)
H OH HO H
CH3 CH3
CH3
CH3
H3C OH
(C) H3C OH (D)
H Br
Br H
H
H
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10. Which of the following reactions are correct?
Br Br
Me Me
HBr
(C)
(D) H /H2 O
Me
HO
Br Me Me Me
Passage – 1
Addition of X2 on alkene is electrophilic addition reaction. Reaction proceed through the formation of 3-
membered cyclic halonium ion. Nucleophile X attacks from backside of cyclic halonium ion hence total
reaction is anti addition reaction. If this reaction proceed in polar solvent then solvent itself acts as
nucleophile.
X
C=C + X2 C=C
X
Mechanism:
Cl2 (1 Mole)
12. CCl4
(A) (B)
Cl
Cl
Cl
(C) (D)
Cl
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Ph CH3
Cl2 ,CH 3 OH
13. C=C Major product:
H H
Ph Ph Ph Ph
H Cl
(A) H Cl (B) H OCH3 (C) H Cl (D) H OCH3
CH3 Cl H3CO H Cl H
H CH3 CH3 CH3
Passage – 2
Addition of HX on alkene proceed through the formation of carbocation. This reaction is also known as
Markownikoff reaction. According to Markkownikoff’s rule addition of electrophile occurs on that carbon of
alkene which have more of ‘H’ atom.
X
HX
Ph CH CH 2 Ph - CH - CH3 + Ph - CH - CH - X
2 2
Major Minor
Mechanism:
(C) (D) CH 3 CH CH 2
CH3
HBr HBr
(C) O2 N CH CH 2 (D) C = CH2
CH3
16. Arrange the following alkenes in decreasing order of reaction with HBr:
CH3 CH3 CH3 CH3
C = CH2 C = CH2 C = CH2 C = CH2
CH3 CH3 O H3C N CH3 - O - CH2
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Passage – 3
P(C 5 H 9 Br)
NaNH2
R S
(C 5 H10 ) (C5 H10 )
Br Br
18. R and S are:
(A) Position Isomers (B) Enantiomers
(C) Geometrical (D) Functional Group Isomers
19. Identify structure of compound T :
O O
(A) CH3 - C - OH (B)
O
(C) CH3 - CH2 - C - OH (D) CH3 - C - H
O O
Passage – 4
Hydroboration oxidation reaction is a process of addition of H2 O according to antimarkownikoff’s rule.
BH3 .THF
CH 3 CH CH 2 CH 3 CH 2 CH 2 OH
H 2 O2 ,O H
OR
2 OH RO - B - OR
O-H
3 R - OH + BO-3 3
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20.
BD3 . THF
18 Major product.
H 2 O2 , OH
HOOC H
BD3 ,THF
21. C=C
D2 O2 ,O D
H COOH
COOH COOH
H D H OD
(A) (B)
H OD H D
COOH COOH
COOH COOH
H D
(C) D H (D)
H OD H OH
COOH COOH
23.
O
(A) 2 (B) O
O
O
(C) (D)
2
24. CH3
|
H–C
|| alkaline KMnO 4
A
H–C
|
CH3
Which is true about this reaction?
(A) A is meso 2, 3-butan-di-ol formed by syn addition
(B) A is meso 1, 2-butan-di-ol formed by anti addition
(C) A is a racemic mixture of 1, 2-butan-di-ol formed by anti addition
(D) A is a racemic mixture of 1, 2-butan-di-ol formed by syn addition
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27. Match the following
Column I Column II
Ph
HBr
(A) C = CH2 P. Free radical
CH3 CH2
CH3
HCl
(B) H D Q. Enantiomer
CD
CH2
CH3
NBS
(C) R. Diastereomer
Ph
HBr
(D) C = CH2
H2 O 2 , hv
S. Carbocation
H3C
HBr
(A) Markownikoff product P. CH 3 CH CH 2
H 2 O2 , hv
H3C CH3
(B) Antimarkownikoff product Q. C=C CHCl 3 KOH
H H
HCl
(C) Peroxide effect R. CH = CH2
HBr
(D) Mixture of stereoisomers S. CF3 CH CH 2
29. Which compound will yield 5-keto-2-methyl hexanal upon treatment with O3 ?
CH3 CH3
CH 3
CH 3
CH3 H3C
(A) (B) (C) (D)
CH3 CH3
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O O
CH3 - C - CH2 - CH2 - C - CH3. The structures are:
31. An alkene of molecular formula C4H8, having zero dipole moment, on treatment with cold
aqueous KMnO4 gives :
(a) optically inactive non resolvable solution (b) optically inactive resolvable solution.
(c) optically active non resolvable solution. (d) optically active resolvable solution.
CH3C=CHCH3
32. The treatment of with hot acidic KMnO4 produces
CH3
(a) CH3COCH3 + CH2O (b) CH3COCH3 + CH3COOH
(c) CH3CHO + CO2 (d) CH3COCH3 only
33. The compound most likely to decolourize a solution of potassium permanganate is
CH3
CH3CCH3
(c) CH3CH=CHCH2CH3 (d)
CH3
34. The olefin, which on ozonolysis gives CH3CH2CHO and CH3CHO?
(a) But1ene (b) But2ene
(c) Pent1ene (d) Pent2ene
35. The ozonolysis of an olefin gives only propanone. The olefin is
(A) propene (B) but–1–ene
(C) but–2–ene (D) 2, 3–dimethylbut–2–ene
36. The treatment of CH3C = CH2
|
CH3
with boiling KMnO4 produces
(A) CH3COCH3 + CH2O (B) CH3CHO + CH3CHO
(C) CH3COCH3 + CO2 (D) CH3COCH3 + HCOOH
37. Select the best starting material for the following reaction:
O 3 ,Zn-H 2 O
?
38. Cyclohexene on reaction with OsO4 followed by reaction with NaHSO3 gives
(a) cisdiol (b) transdiol
(c) epoxide (d) alcohol
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ANSWER KEY
SHEET – 5 – ALKENE
(Properties of Alkenes)
1. B
2. A
3. C
4. B
5. C
6. B
7. C
8. B
9. BC
10. ABC
11. A
12. B
13. D
14. C
15. D
16. B
17. A
18. C
19. B
20. B
21. C
22. C
23. B
24. A
25. A
26. C
27. A Q, S; B R, S; C P, Q; D P, Q
28. A R, S; B P, S; C P; D Q, R
29. B
30. A, B, C
31. B
32. B
33. C
34. D
35. D
36. C
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