Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Question
You are trying to monobrominate methylcyclopentane to form a compound with the molecular formula C6H11Br. Using the relative reactivities for bromination in the picture, calculate the percentages of each isomer expected for this reaction.
![Relative Reactivities of the Four Types of Alkane C-H Bonds
in Halogenations
Table 3-6
Cl·
(25°C, gas)
F.
Br.
C-H bond
(25°C, gas)
(150°C, gas)
0.5
0.004
0.002
CH3-H
RCH2-H"
R2CH-H
R3C-H
1
1
1
1.2
80
1.4
1700
"For each halogen, reactivities with four types of alkane C-H bonds are normalized to the reactivity of the
primary C-H bond.
сХ Вond
Table 6-1 Lengths and Bond
Strengths in CH,X
Bond
084
strength
[kcal
mol-1
methane (Å) (kJ mol-)]
Bond
Halo-
length
CH;F
1.385
110
(460)
CH;Cl
1.784
85
(356)
CH;Br
1.929
70
(293)
CH;I
2.139
57
(238)
greasing bond length
precrasne bond strength](https://content.bartleby.com/qna-images/question/a069fef9-98b1-4ecc-ba7b-de0f9fee4745/65eacb7b-8b10-4543-acdf-3ece901ed690/y69mt0q_processed.jpeg)
Transcribed Image Text:Relative Reactivities of the Four Types of Alkane C-H Bonds
in Halogenations
Table 3-6
Cl·
(25°C, gas)
F.
Br.
C-H bond
(25°C, gas)
(150°C, gas)
0.5
0.004
0.002
CH3-H
RCH2-H"
R2CH-H
R3C-H
1
1
1
1.2
80
1.4
1700
"For each halogen, reactivities with four types of alkane C-H bonds are normalized to the reactivity of the
primary C-H bond.
сХ Вond
Table 6-1 Lengths and Bond
Strengths in CH,X
Bond
084
strength
[kcal
mol-1
methane (Å) (kJ mol-)]
Bond
Halo-
length
CH;F
1.385
110
(460)
CH;Cl
1.784
85
(356)
CH;Br
1.929
70
(293)
CH;I
2.139
57
(238)
greasing bond length
precrasne bond strength
Expert Solution
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Step 1
Given:
The relative reactivities of type of alkane bonds:
RCH2-H (1o) : R2CH-H (2o) : R3CH-H (3o) = 1 : 80 : 1700
We have to monobrominate methylcyclopentane and calculate the percentage of each isomer expected.
Step by stepSolved in 2 steps with 1 images
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