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Organic chemistry question on aldol reaction?

davejim

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12 years ago

Organic chemistry question on aldol reaction?

True or false: In the presence of hydroxide, either acetaldehyde or propanal can serve as a nucleophile in an aldol reaction.

True or false: Either acetaldehyde or propanal can serve as an electrophile in an aldol reaction.

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ilikelamp

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#1

12 years ago

They are both true. In the presence of hydroxide, each aldehyde can enolize to form a nucleophilic enolate anion. The enolate can react with an unionized aldehyde in the first step of an aldol condensation. The unionized aldehyde is an electrophile in this reaction.

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