Suggest a mechanism (show electron movement, intermediates, and resonance forms if relevant, but not transition states) for the following carbonyl condensation reaction. This is probably not a transformation you have seen before now, each step is like others you have seen and you should be able to reason your way through it. No additional reagents other than those shown are necessary. R' NaOCH2CH3 R' R H₂C OCH2CH3 ་བྱ།ན་ OCH2CH3 CI R + NaCl + CH3CH2OH Propose a synthesis of the following ketone in a few steps starting from toluene (methyl benzene). You will get full credit by showing both the retrosynthetic analysis and the forward reaction scheme (reagents & conditions). Hint: you may find the reagent N-bromosuccimide to be useful for introducing functionality.

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 16.65P: All rearrangements we have discussed so far have involved generation of an electron-deficient carbon...
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Suggest a mechanism (show electron movement, intermediates, and resonance forms if
relevant, but not transition states) for the following carbonyl condensation reaction. This is probably
not a transformation you have seen before now, each step is like others you have seen and you
should be able to reason your way through it. No additional reagents other than those shown are
necessary.
R'
NaOCH2CH3
R'
R
H₂C
OCH2CH3
་བྱ།ན་
OCH2CH3
CI
R
+ NaCl + CH3CH2OH
Transcribed Image Text:Suggest a mechanism (show electron movement, intermediates, and resonance forms if relevant, but not transition states) for the following carbonyl condensation reaction. This is probably not a transformation you have seen before now, each step is like others you have seen and you should be able to reason your way through it. No additional reagents other than those shown are necessary. R' NaOCH2CH3 R' R H₂C OCH2CH3 ་བྱ།ན་ OCH2CH3 CI R + NaCl + CH3CH2OH
Propose a synthesis of the following ketone in a few steps starting from toluene (methyl
benzene). You will get full credit by showing both the retrosynthetic analysis and the forward
reaction scheme (reagents & conditions). Hint: you may find the reagent N-bromosuccimide to be
useful for introducing functionality.
Transcribed Image Text:Propose a synthesis of the following ketone in a few steps starting from toluene (methyl benzene). You will get full credit by showing both the retrosynthetic analysis and the forward reaction scheme (reagents & conditions). Hint: you may find the reagent N-bromosuccimide to be useful for introducing functionality.
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