(c) Treatment of the molecule shown below with NBS in the presence of light produces a mixture of four major monobrominated compounds (including stereoisomers). Draw the structures of these products.
(c) Treatment of the molecule shown below with NBS in the presence of light produces a mixture of four major monobrominated compounds (including stereoisomers). Draw the structures of these products.
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
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Transcribed Image Text:(c) Treatment of the molecule shown below with NBS in the presence of light produces a mixture of four major
monobrominated compounds (including stereoisomers). Draw the structures of these products.
Transcribed Image Text:Bond Dissociation Lnergies of Relevant Bonds (kJ:mol)
CIL-CII,
368
CI-Br
CII,CIL-BT
293
Br-Br
193
CILCIL-II 410
285
II- Br
368
Two possible reactions of chlorine with cthanc are shown below:
light
(A) H3C-CH3
Br-Br
CH3CH,Br
HBr
light
(B) H3C-CH3
Br-Br
2 CH;Br
(a) Deduce which of thesc rcactions is favored based on calculations using the data in the Tablc.
Explain any assumptions in your calculations. Thesc are simple calculations. Calculators are not needed. Show
your calculations and explain your reasoning.
(b) Assuming that the two reactions shown in part (a) follow a radical chain mcchanism complete the
mechanisms for both rcactions by filling in the missing information in the mechanism shown.
light
Reaction A: H,C-CH3
Br-Br
CH;CH,Br
HBr
Initiation step:
Br-Br
2 Br
(show arrows)
Propagation step 1: CH3-CH3
Br*
(show arrows and products)
Propagation step 2:
write out reaction and mechanism for step 2
light
Reaction B:
H3C-CH3
Br-Br
2 CH;Br
Initiation step:
2 Br
ishow arrows)
Br-Br
Propagation step 1: CH3-CHg
CH3-Br + "CH3 (show arrows)
Br
Propagation step 2:
write out reaction and mechanism for step 2
13
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