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Chapter 19: Q85E (page 648)

When glucose (Problem 19-52) is treated with NaBH4 , reaction occurs to yield sorbitol, a polyalcohol commonly used as a food additive. Show how this reduction occurs.

Short Answer

Expert verified

Reduction followed as:

Step by step solution

01

Reduction with sodium borohydride

Sodium borohydride NaBH4 is the mild reducing agent which is used to reduce the aldehyde and ketone carbonyl group to the alcohol. It reduces aldehyde to primary alcohol and ketone to secondary alcohol it do not reduce the higher carbonyl like carboxylic acid and ether so, it is a mild reagent.

02

Reduction of glucose with sodium borohydride

As glucose contain the aldehyde group and sodium borohydride is the basic reducing agent so it abstracts the proton of the aldehyde followed by hydrolysis convert the carbonyl into the hydroxyl group as the primary alcohol is formed in sorbitol as shown below:

Reduction of Glucose

03

Reduction of glucose

Reduction of glucose to form sorbitol is followed by hydrolysis by converting the open aldehyde to alcohol group.

Compound Formation

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