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Chapter 21: 28P (page 817)

Draw a stepwise mechanism for the following reaction

Short Answer

Expert verified

The gem-diols would undergo hydration in acidic medium to give the corresponding carbonyl compound.

Consider the hydrolysis of the given gem-diol. One among the hydroxyl group is protonated in the acidic medium.

Protonation of diol

Step by step solution

01

Hydrolysis of diols

The gem-diols would undergo hydration in acidic medium to give the corresponding carbonyl compound.

Consider the hydrolysis of the given gem-diol. One among the hydroxyl group is protonated in the acidic medium.

Protonation of diol

02

Dehydration

The protonated hydroxy group leaves forming a cation. The cation is further stabilized by resonance.

Dehydration reaction

03

Deprotonation

The proton donates a pair of electrons for the pi-bond formation of the carbonyl compound.

Formation of ketone

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Hydroxy aldehydes A and B readily cyclize to form hemiacetals. Draw the stereoisomersformed in this reaction from both A and B. Explain why this process gives an opticallyinactive product mixture from A, and an optically active product mixture from B.

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