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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 Grignard reagent and carbonyl compound are needed to prepare each alcohol? As shown in part (d), 3o alcohols with three different R groups on the carbon bonded to the OH group can be prepared by three different Grignard reactions.

What epoxide is needed to convertCH3CH2MgBrto each of the following alcohols, after quenching with water?

a.

b.

c.

d.

Question: Cinnamoylcocaine, a natural product that occurs in coca leaves, can be converted tococaine by the following reaction sequence. Identify the structure of cinnamoylcocaine, aswell as intermediates X and Y.

Write the step(s) needed to convert CH3CH2Brto each reagent: (a)CH3CH2Li (b) CH3CH2MgBr(c) (CH3CH2)2CuLi

Draw the product formed when the α,β-unsaturated ketone A is treated with each reagent.

(a) NaBH4, CH3OH

(b) H2 (1 equiv), Pd-C

(c) H2 (excess), Pd-C

(d) [1] CH3Li ; [2]H2O

(e) [1] CH3CH2MgBr ; [2]H2O

(f) [1] (CH2=CH2)2; [2]H2O

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