c) When compound A is treated with the strong base lithium diisopropylamine (LDA) followed by an acidic workup compound c forms. Provide a plausible mechanism for this reaction. i) LDA Ph then acidic workup Ph Li A LDA = H3C, .N. CH3 CH3 CH3

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.47P: The base-promoted rearrangement of an -haloketone to a carboxylic acid, known as the Favorskii...
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Need help with part c). Thank you :)

Consider the following structure A.
Ph
A
a) Indicate the most electrophilic carbon. Use resonance to justify your answer.
b) The bold hydrogen in compound A is the most acidic. Using resonance indicate why the
carbanion formed by its removal is the most stable. ·
H
Ph
A
c) When compound A is treated with the strong base lithium diisopropylamine (LDA) followed
by an acidic workup compound c forms. Provide a plausible mechanism for this reaction.
.H
i) LDA
Ph
then acidic workup
Ph
Li
A
B
CH3
LDA = H3C.
ČH3 CH3
Transcribed Image Text:Consider the following structure A. Ph A a) Indicate the most electrophilic carbon. Use resonance to justify your answer. b) The bold hydrogen in compound A is the most acidic. Using resonance indicate why the carbanion formed by its removal is the most stable. · H Ph A c) When compound A is treated with the strong base lithium diisopropylamine (LDA) followed by an acidic workup compound c forms. Provide a plausible mechanism for this reaction. .H i) LDA Ph then acidic workup Ph Li A B CH3 LDA = H3C. ČH3 CH3
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