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?
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...
Related questions
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?](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F232c193f-1047-4ccf-95ea-de8c042edd9d%2F0599e7b0-4217-416b-890b-21605557bdaf%2Fggw55zi_processed.jpeg&w=3840&q=75)
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?
AI-Generated Solution
AI-generated content may present inaccurate or offensive content that does not represent bartleby’s views.
Unlock instant AI solutions
Tap the button
to generate a solution
Recommended textbooks for you
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY