4. On the basis of your mechanism for Problem 3(c), answer the following questions: (a) Additions of Br₂ and ArSCI to [2.2.1]-bicycloheptene give the products shown in Equa- tions 11 and 12, respectively. Give a mechanism for the products of Reaction 11 and explain why only the bromination gives rearrangement products. Br Br Br +Br₂- D.A. dr. A D--- + ArSCI→ Br SAr (11) (12) -CH=CH₂ reacts 1000 times faster than Ph-CH-CH₂ with Brg-HOAC but only 3.8 times faster with pC1-CH₂SCI in HOAc at 25°C. Explain. (c) Which would you expect to show a better linear correlation with the rate constants for bromination of a number of alkenes-the rate constants for hydration or those for addition of ArSCI to the same alkenes?

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...
Question
4. On the basis of your mechanism for Problem 3(c), answer the following questions:
(a) Additions of Br₂ and ArSCI to [2.2.1]-bicycloheptene give the products shown in Equa-
tions 11 and 12, respectively. Give a mechanism for the products of Reaction 11 and
explain why only the bromination gives rearrangement products.
Br
Br
Br
+Br₂-
D.A. dr. A
D---
+ ArSCI→
Br
SAr
(11)
(12)
-CH=CH₂ reacts 1000 times faster than Ph-CH-CH₂ with Brg-HOAC but only
3.8 times faster with pC1-CH₂SCI in HOAc at 25°C. Explain.
(c) Which would you expect to show a better linear correlation with the rate constants for
bromination of a number of alkenes-the rate constants for hydration or those for
addition of ArSCI to the same alkenes?
Transcribed Image Text:4. On the basis of your mechanism for Problem 3(c), answer the following questions: (a) Additions of Br₂ and ArSCI to [2.2.1]-bicycloheptene give the products shown in Equa- tions 11 and 12, respectively. Give a mechanism for the products of Reaction 11 and explain why only the bromination gives rearrangement products. Br Br Br +Br₂- D.A. dr. A D--- + ArSCI→ Br SAr (11) (12) -CH=CH₂ reacts 1000 times faster than Ph-CH-CH₂ with Brg-HOAC but only 3.8 times faster with pC1-CH₂SCI in HOAc at 25°C. Explain. (c) Which would you expect to show a better linear correlation with the rate constants for bromination of a number of alkenes-the rate constants for hydration or those for addition of ArSCI to the same alkenes?
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