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Ketone and Aldehyde Synthesis Reactions

21. Aldehydes and Ketones: Nucleophilic Addition / Ketone and Aldehyde Synthesis Reactions / Problem 4

Problem 4

Geminal diols are known to lose water spontaneously to give carbonyl compounds. Draw a mechanism for the formation of pentan-3-one from pentane-3,3-diol via acid-catalyzed dehydration.

A

Detailed mechanism of pentane-3,3-diol dehydration to form pentan-3-one.

B

Alternative mechanism for pentane-3,3-diol dehydration to pentan-3-one.

C

Another representation of the dehydration mechanism for pentane-3,3-diol to pentan-3-one.

D

Final mechanism illustration of pentane-3,3-diol converting to pentan-3-one.