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Chapter 22: Q84. (page 923)

Question. Draw a stepwise mechanism for the following reaction, the last step in a five-step industrial synthesis of vitamin C that begins with the simple carbohydrate glucose.

Short Answer

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Answer

Step 1:

Step 2:

Step by step solution

01

Step by Step solutionStep 1: Hydrolysis of acetal groups

The acetal groups will be hydrolyzed in presence of acid and can form the respective carbonyl compounds.

In this reaction, it forms two moles of acetone and a furan substituent.

02

Formation of vitamin C

During this reaction, the furan substituent that is formed will be converted into Vitamin C in presence of acid.

03

Mechanism of the reaction

Step 1:

Step 2:

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Most popular questions from this chapter

What reagent is needed to convert (CH3)2CHCH2COCIinto each compound?

a.

b.

c.

d.

Draw a stepwise mechanism for the following reaction. Your mechanism must show how both organic products are formed.

Draw two different ways to prepare each ketone from an acid chloride and an organocuprate reagent.

a.

b.

Question: Which ester, C or D, is more reactive in nucleophilic acyl substitution? Explain your reasoning.

Question: Draw the products of each reaction

a.

b.

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