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Chapter 26: Q 35. (page 1071)

In addition to using CHX3and base to synthesize dihalocarbenes (Section 26.4), dichlorocarbene (CCL2)can be prepared by heating sodium trichloroacetate. Draw a stepwise mechanism for this reaction.

Short Answer

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Answer

Mechanism

Step by step solution

01

 α-elimination reaction

The 1,1-elimination or α-elimination reaction involves the elimination of two groups from the same carbon atom.

02

Stability  

The dichlorocarbene compound is more stable than the trichloromethanide ion, as the dichlorocarbene compound is neutral.

03

Mechanism of the given reaction

Sodium trichloroacetate, upon heating, loses a carboxyl COOgroup, resulting in the formation of sodium-trichloromethanide. The trichloride ion loses a chloride ion to achieve greater stability and form dichlorocarbene.

The mechanism of the given reaction is shown below.

Mechanism

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