11. What alkenes would you start with to prepare the following products? (a) Br (a) (b) Vinylcyclohexane CH₂CH3 HBr 12. Show the structures of the carbocation intermediates you would expect the following reactions: CH3 CH3 CHCH3 HI ? CH3CH₂C=CHCHCH3 HBr ? (c) CH₂CH3 Br Br CH3CH₂CHCH₂CH₂CH3 (b) 13. On treatment with HBr, vinylcyclohexane undergoes addition and rearrangement to yield 1-bromo- 1-ethylcyclohexane. Using curved arrows, propose a mechanism to account for this result. (d) CI 1-Bromo-1-ethylcyclohexane

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Chapter1: Chemical Foundations
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11. What alkenes would you start with to prepare the following products?
(a)
-Br
(b)
Vinylcyclohexane
CH₂CH3
HBr
HBr
12. Show the structures of the carbocation intermediates you would expect in the following reactions:
(a)
CH3 CH3
CHCH3 HI ?
CH3CH₂C=CHCHCH3
?
(b)
Br
CH3CH₂CHCH₂CH₂CH3
CH₂CH3
Br
13. On treatment with HBr, vinylcyclohexane undergoes addition and rearrangement to
1-ethylcyclohexane. Using curved arrows, propose a mechanism to account for this result.
(d)
1-Bromo-1-ethylcyclohexane
CI
1-bromo-
Transcribed Image Text:11. What alkenes would you start with to prepare the following products? (a) -Br (b) Vinylcyclohexane CH₂CH3 HBr HBr 12. Show the structures of the carbocation intermediates you would expect in the following reactions: (a) CH3 CH3 CHCH3 HI ? CH3CH₂C=CHCHCH3 ? (b) Br CH3CH₂CHCH₂CH₂CH3 CH₂CH3 Br 13. On treatment with HBr, vinylcyclohexane undergoes addition and rearrangement to 1-ethylcyclohexane. Using curved arrows, propose a mechanism to account for this result. (d) 1-Bromo-1-ethylcyclohexane CI 1-bromo-
2 Predict the products of the following reactions. Don't worry about the size of
the molecule; concentrate on the functional groups.
H₂C
HO
CH3
CH3
Cholesterol
OH
CH₂
Br
&a,
CH₂
of of
CH,
CH;
Br₂
HBr
1. Os04
2. NaHSO3
CH₂
1. BH3, THF
2. H₂O₂, OH
CH₂I2, Zn(Cu)
A?
B?
C?
D?
E?
Transcribed Image Text:2 Predict the products of the following reactions. Don't worry about the size of the molecule; concentrate on the functional groups. H₂C HO CH3 CH3 Cholesterol OH CH₂ Br &a, CH₂ of of CH, CH; Br₂ HBr 1. Os04 2. NaHSO3 CH₂ 1. BH3, THF 2. H₂O₂, OH CH₂I2, Zn(Cu) A? B? C? D? E?
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