(c) Treatment of the molecule shown below with NBS in the presence of light produces a mixture of four majormonobrominated compounds (including stereoisomers). Draw the structures of these products. Bond Dissociation Lnergies of Relevant Bonds (kJ:mol)CIL-CII,368CI-BrCII,CIL-BT293Br-Br193CILCIL-II 410285II- Br368Two possible reactions of chlorine with cthanc are shown below:light(A) H3C-CH3Br-BrCH3CH,BrHBrlight(B) H3C-CH3Br-Br2 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. Showyour calculations and explain your reasoning.(b) Assuming that the two reactions shown in part (a) follow a radical chain mcchanism complete themechanisms for both rcactions by filling in the missing information in the mechanism shown.lightReaction A: H,C-CH3Br-BrCH;CH,BrHBrInitiation step:Br-Br2 Br(show arrows)Propagation step 1: CH3-CH3Br*(show arrows and products)Propagation step 2:write out reaction and mechanism for step 2lightReaction B:H3C-CH3Br-Br2 CH;BrInitiation step:2 Brishow arrows)Br-BrPropagation step 1: CH3-CHgCH3-Br + "CH3 (show arrows)BrPropagation step 2:write out reaction and mechanism for step 213

NBS is N- Bromo succinimide which give radical substitution

Answered: (c) Treatment of the molecule shown…

(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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Sulfur Functional Groups

Many organic molecules contain sulfur functional groups and have their own importance in chemistry as well as biology. Some of the organic molecules which contain sulfur functional groups and the corresponding sulfur functionality is given below:

Question

(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.

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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