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Chapter 28: Question 28.34 (page 1141)

Draw a stepwise mechanism for the conversion of 尾-D-glucose to both anomers of N-ethyl glucopyranoside, the equation written in Reaction [1].

Short Answer

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Answer

Mechanism

Step by step solution

01

β-D-glucose

In the尾-D-glucose, the configuration at C-1 and C-5 carbons are trans to each other. This compound reacts with an amine under mildly acidic conditions forms a carbocation intermediate.

02

Carbocation

The hydroxyl group reacts with the proton and formsH2O+ ; after losing thisH2O+ during the reaction, a carbocation intermediate is formed.

The shape of the carbocation is planar, and the nucleophile can attack it both above and below the plane and forms alpha and beta-N-ethyl glycopyranoside.

03

Mechanism

The mechanism involves the formation of a carbocation in step 1 and the attack of the nucleophile on the carbocation in step 2.

Stepwise mechanism

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