Using the relative reactivities for bromination in the picture, calculate the percentages of each isomer expected for this reaction.

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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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
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
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.

               

 

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