Dimethyl cyclopropanes can be prepared by the reaction of an a,ß-unsaturated carbonyl compound X with two equivalents of a Wittig reagent Y. Propose a stepwise mechanism for this reaction.

Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
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Dimethyl cyclopropanes can be prepared by the reaction of an a,ß-unsaturated carbonyl compound X
with two equivalents of a Wittig reagent Y. Propose a stepwise mechanism for this reaction.
CH;O.
Ph;P=
CH;O
H.
(2 equiv)
Y.
Step [1]:
0, PPh3
CH;O.
CH;O.
H.
Ph3P
es
PPH3 O
PPH3
CH;O.
H.
CH30.
H.
Step [2]:
CH;0.
CH;0.
H.
O-PPH3
Ph;P=
Transcribed Image Text:Be sure to answer all parts. Dimethyl cyclopropanes can be prepared by the reaction of an a,ß-unsaturated carbonyl compound X with two equivalents of a Wittig reagent Y. Propose a stepwise mechanism for this reaction. CH;O. Ph;P= CH;O H. (2 equiv) Y. Step [1]: 0, PPh3 CH;O. CH;O. H. Ph3P es PPH3 O PPH3 CH;O. H. CH30. H. Step [2]: CH;0. CH;0. H. O-PPH3 Ph;P=
Step [3]:
PPH3
CH;0.
CH3O.
Phop-)
H.
PPH3 O
CH;0.
CH;0.
H.
Ph;P
Step [4]:
CH30
CH;0.
Ph;P
Ph3P-
0,PPH3
CH30
CH;O
H.
0-PPH3
CH30
Transcribed Image Text:Step [3]: PPH3 CH;0. CH3O. Phop-) H. PPH3 O CH;0. CH;0. H. Ph;P Step [4]: CH30 CH;0. Ph;P Ph3P- 0,PPH3 CH30 CH;O H. 0-PPH3 CH30
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