Treatment of cyclopentane-1,3-dione with iodomethane in the presence of base leads mainly to a mixture of three

Question:

Treatment of cyclopentane-1,3-dione with iodomethane in the presence of base leads mainly to a mixture of three products.

CH3 CH3 NaOH, CHJ, CH,CHОН + CH3 OCH; A B

(a) Give a mechanistic description of how these three products are formed.

(b) Reaction of product C with a cuprate reagent results in loss of the methoxy group. For example,

Suggest a mechanism for this reaction, which is another synthetic route to enones substituted at the β-carbon

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Related Book For answer-question

Organic Chemistry structure and function

ISBN: 978-1429204941

6th edition

Authors: K. Peter C. Vollhardt, Neil E. Schore

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Question Posted: May 07, 2020 03:33 AM

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Treatment of cyclopentane-1,3-dione with iodomethane in the presence of base leads mainly to a mixture of three

Question:

CH3 CH3 NaOH, CHJ, CH,CHОН + CH3 OCH; A B

Step by Step Answer:

Solution a I II III b H A 00 Na OH CH3 OH Na CH3 m O CH3 0 H O CH3 i CH CH CH CH2 CuLi THF HH...View the full answer

Organic Chemistry structure and function

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