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Chapter 26: Q 55. (page 1075)

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

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Answer

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01

Wittig Reaction

The organic reaction involving the conversion of carbonyl compounds to alkenes using the ylide reagent is known as the 鈥榃ittig Olefination鈥�.

02

Mechanism

a. The ylide of the phosphonium salt would attack the carbonyl carbon forming a C-C bond.

Carbonyl compound reacts with phosphonium ylide

b. The nucleophilic carbon would attack the electrophilic carbon center as the pi-electrons are delocalized.

Delocalisation of pi-electrons

c. The lone pair of electrons on the carbon would attack the electrophilic ylide to form a new C-C bond.

Formation of product

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