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Question

Draw the structures of compounds A, B and C.
(C2H5)3N:+:CCl2A (An unstable adduct)
AB+C2H4
BH2OC

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Solution

In the first reaction, dichlorocarbene adds to triethylamine to form an unstable adduct A.

In the second step, this unstable adduct loses a molecule of ethylene to form product B. The hydrolysis of product B gives product C. In this step, the dichloro methyl group is hydrolyzed to aldehyde group.

The structures of compounds A to C are as follows:

(C2H5)3N:+:CCl2Et3N+CCl2A (An unstable adduct)

Et3N+CCl2AEt2NCHCl2B+C2H4

Et2NCHCl2BH2OEt2NCHOC


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