5.

ALKENES & ALKYNES

5.1 (B)

5.2 (A)

5.3 (C)

5.4 (B)

5.5 (B)

5.6 (C) Trans additions of – OH and ‘D’ at C=C is taking place.

5.7 (C)

5.8 (D) The least stable alkene has highest value of heat of hydrogenation.

5.9 (B)

5.10 (C) Rate is according to stability of carbonation formed.

5.11 (D)

HBr / R 2O 2 HBr / dark

5.12 (D) Ph - C  CH   Ph – CH = CHBr   Ph – CH CH2
| |
Br Br

5.13 (A)

2CH 3MgBr
5.14 (A) CH 3  CH  CH 2  C  CH   CH 3  CH  CH 2  C  C  MgBr  2Ch 4 
| |
OH OMgBr

CH3 H CH 3
| | |
5.15 (A) 
CH 3  CH  C  CH 3  C  C  H 
 CH 3  C  C  C  CH 3
| || | |
H O O H
5.16 (B)

5.17 (A) + M group stabilisers carbocation effectively therefore fast rate of

electrophilic addition.

5.18 (C)

5.19 (D)

O
||
(i) KMnO 4 / H 2O / Δ
5.20 (A) (ii) H O 
 HOOC  C  CH 2  CH 2  CH 2  CH 2  COOH
3

5.21 (C)
5.22 (C)

(Markownikov’s Anti addition)

5.23 (C)

 Ph  C  CHCl2   Ph  C  CH 
   || || 
Θ
HOCl NaOH OH
Ph – C  CH   ||
(excess)     
Internalcannizaro
 O   O O 
reaction
 
H
|
Ph  C  CO-
| ||
OH O
( )

5.24 (A, B, D)
Option (C) correctly represent this reaction

Θ
ZnCl 2
 Iδ + Clδ  
IC + ZnCl2   (I, Zn C l3 )

5.25 (A, B, C)
C  CBu C  CBu
| |
Θ  Θ 
LiNH 2 Ph  CH  O H2 O
Cu  C  C  H   Bu  C  C L i   Ph  CH  O Li   Ph  CH  OH
(A) (B)
5.26 (A, B)

 
H (H3O
(I) CH2 = C = CH2   CH2 = C - CH2 = C – CH3 - H 


| |

H OH2

tautomerisation
CH3 – C – CH3   CH2 = C – CH3
|| |
OH O

H2SO4 / Hg
(II) CH3 – C  CH 
2+
tautomerisation
 CH3 – C = CH2   CH3 – C – CH3
| ||
OH O

BH3 / THF tautomerisation

(III) CH3 – C  CH 
anti Markonikov
 CH3 – CH = CH – OH   CH3 CH2 – CHO

5.27 (A) 5.28 (A) 5.29 (A) 5.30 (D) 5.31 True

5.32 False ; 3 moles are required; one mole goes in acid base reaction.

5.33 (B) 5.34 (C) e5.35 (A) 5.36 (B) 5.37 (C)

OH
|
Al 2O3 HI
5.38 (B) (CH3)2CHCHOHCH3 
250°C
 CH3 – C = CH3 
AgOH
 CH3 – C – CH2 – CH3
(A) | |
CH3 CH3
(B) (C)

Al 2O3 (i) B 2 H 6

150°C
 CH3 – C = CH – CH3 
(ii) H O , OH 
 (CH3)2 CHCHOHCH3
2 2

|
CH3 (A)
(B)

5.39 (A  s); (B  p); (C  q); (A  r)

 
D OD 2
(A) Ph – C  CD   Ph – C = CD2   PhC = CD2 tautomerisation
 Ph – C = CD2 
| |
 OD2 OD

PhC – CD3
||
O
 (B)

B2H6 / THF
(C)
OHΘ / H2O2  (antimarkonikov addition)


B2 H6 / THF Tautomerisation
(D) PhC = CD   PhC = CD 
 PhC = CD   Ph – CD2 – CDO
OH Θ / H 2O 2
| | | |
D BD2 D OD

5.40 (A)

Eriantiomers Opticallyactive.
Total stereoisomers – 3
Optically active - 2 ; optically inactive -1

(B)
 Lindlar
CH3 
Syn


Lindlar

Syn


Total Stereoisomer – 3
Optically active – 2 ; Optically inactive – 1

Na / liqNH 3
(C)  anti


Na / liqNH 3
 anti


Na / liqNH 3
 anti


Both R, R and S, S on reduction will give one stereoisomer optically active.

Total - 3 : optically active - 2 ; optically inactive - 1.

(D)
Ans. (a) 3 (b) 3 Optically active - 2 ; Optically inactive -1
(c) 3 Optically active - 2 ; Optically inactive -1 (d) 2 racemic.

5.41

Total No. of possible products

Ans. 4

5.42 Total 3 chiral center without symmetry so total products m = 23 = 8.

All optically active.

5.43 Some initially formed singlet carbene consume collides with inert gas molecule and
changes to triplet.

Trans optically active

Total 3 sterecisomers: 2 optically active ; 1 optically inactive

5.44 Two Geometrical centers ; Total isomers = 22 = 4.

H
Ans. 4