Hemiacetal and Acetal Functional Groups Hemiacetal: alcohol and ether on same carbon Acetal: Two ethers on same carbon.

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Presentation transcript:

Hemiacetal and Acetal Functional Groups Hemiacetal: alcohol and ether on same carbon Acetal: Two ethers on same carbon

Mechanism Must be acid-catalyzed. Adding H + to carbonyl makes it more reactive with weak nucleophile, ROH. Hemiacetal forms first, then acid-catalyzed loss of water, then addition of second molecule of ROH forms acetal. All steps are reversible. =>

Hemiacetal Synthesis: aldehyde + alcohol Alcohol + aldehyde --> hemiacetal Ethanal + methanol Alcohol oxygen becomes an ether Carbon double bond oxygen becomes an alcohol

Mechanism for Hemiacetal =>

Aldehyde and Ketone Reactions

Synthesis of Acetal Functional Group Acetal: alcohol plus hemiacetal (ether synthesis) Acetal: Two ethers on same carbon

=>

Aldehyde and Ketone Reactions

Mechanism Hemiacetal to Acetal =>

Cyclic Acetals Addition of a diol produces a cyclic acetal. Sugars commonly exist as acetals or hemiacetals. =>

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