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Chapter 22: Q21. (page 896)

Question: What product is formed when the esters in ginkgolide B, the chapter-opening molecule, are hydrolyzed in aqueous acid? Indicate the stereochemistry of all stereogenic centers.

Ginkgolide B

Short Answer

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Answer

Step by step solution

01

Step-by-Step SolutionStep 1: The reaction of esters with aqueous acid

The esters react with aqueous acids to undergo hydrolysis, which takes place by the reversible equilibrium reaction. The equilibrium is shifted to the right towards the formation of carboxylic acid by the addition of excess water.

This mechanism involves the addition of the nucleophile and the elimination of the leaving group.

02

The ester hydrolysis of the ginkgolide B

The ester hydrolysis of the ginkgolide B results in the formation of the following products:


Representation of ester hydrolysis

The esters in the above reactant changes into the carboxylic acid groups. The stereo centers in the above molecule are marked as R and S in the structure.

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Most popular questions from this chapter

Question:What reagents are needed to convert phenylacetonitrile (C6H5CH2CN) to each compound:

a.C6H5CH2CO(CH3)b.C6H5CH2COC(CH3)3c.C6H5CH2CHOd.C6H5CH2COOH

stereochemistry of the products of reduction depends on the reagent used,as you learned in Sections 20.5 and 20.6. With this in mind, how would you convert3,3-dimethylbutan-2-one [CH3COC(CH3)3] to: (a) racemic 3,3-dimethylbutan-2-ol[CH3CH(OH)C (CH3)3] ;(b) only (R)-3,3-dimethylbutan-2-ol; (c) only (S)-3,3-dimethylbutan-2-ol?

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