Help with Wittig Reactions - Organic Chemistry

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Question

All of the following are characteristics of a Wittig reaction except __________.

Answer

The Wittig reaction involves the reaction of a phosphonium ylide (generated by treating a phosphonium salt with a strong base) with a ketone or aldehyde.

The reaction proceeds through a phosphaoxetane (4-membered ring containing both phosphorus and oxygen) intermediate to generate a new compound containing a carbon-carbon double bond, plus a phosphine oxide byproduct. It does not form trans double bonds exclusively; sometimes, a mixture of cis and trans isomers are obtained, and sometimes the cis isomer is the predominant product.

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Question

What is the final organic product of the reaction shown?

Screen shot 2015 11 14 at 11.07.54 am

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Answer

First step: esterification

Second step: reduction

Third step: neutralization

Fourth step: oxidation to aldehyde

Fifth step: alkene metathesis

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