Question: Additional evidence for the halogenation mechanisms that we just presented comes from the following facts: (a) Optically active 2-methyl-1-phenylbutan-1-one undergoes acid-catalyzed racemization at a rate

Additional evidence for the halogenation mechanisms that we just presented comes from the following facts:
(a) Optically active 2-methyl-1-phenylbutan-1-one undergoes acid-catalyzed racemization at a rate exactly equivalent to the rate at which it undergoes acid- catalyzed halogenation.
(b) 2-Methyl-1-phenylbutan-1-one undergoes acid-catalyzed iodination at the same rate that it undergoes acid-catalyzed bromination.
(c) 2-Methyl-1- phenylbutan-1-one undergoes base-catalyzed hydrogen-deuterium exchange at the same rate that it undergoes base-promoted halogenation. Explain how each of these observations supports the mechanisms that we have presented.

Step by Step Solution

3.32 Rating (158 Votes )

There are 3 Steps involved in it

1 Expert Approved Answer
Step: 1 Unlock

a The slow step in basecatalyzed racemization is the same as that in basepromoted haloge... View full answer

blur-text-image
Question Has Been Solved by an Expert!

Get step-by-step solutions from verified subject matter experts

Step: 2 Unlock
Step: 3 Unlock

Document Format (1 attachment)

Word file Icon

877-C-O-CA (256).docx

120 KBs Word File

Students Have Also Explored These Related Organic Chemistry Questions!