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Chapter 28: Question 28.18 (page 1125)

Draw a stepwise mechanism for the following reaction.

Short Answer

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Answer

The mechanism of the above reaction is followed by resonance and nucleophilic attack of H2O to form anomers.

Step by step solution

01

Glycoside

Glycoside is the molecule formed from monosaccharide, which undergoes condensation with a hydroxyl group and eliminates water.Glycosides have hemiacetal and hydroxyl groups, which on hydrolysis gives two anomers.

02

Formation of carbocation

Glycoside is hydrolyzed and forms an intermediate by the loss of H2O , which on resonance gives carbocation.

03

Formation of anomers

Carbocation was attacked by H2O on both sides (above and below). The carbocation forms an intermediate that undergoes nucleophilic attack to form αandβanomers, as shown below:

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Convert each compound to a Fischer projection and label each stereogenic center as R or S.

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