Complete the synthesis of the following reaction:

Question:

Complete the synthesis of the following reaction:

Reactions of Esters:

Esters are carboxylic acid derivatives prepared by the acid catalyzed reaction between a carboxylic acid and an alcohol. An ester can be reduced to a primary alcohol by reacting it with lithium aluminum hydride.

Answer and Explanation:

The steps needed to complete the synthesis are given below.

Step 1: Reduction of the ester using lithium aluminum hydride gives the primary alcohol upon acidic workup.

Step 2: Dehydration of the primary alcohol by reacting it with sulfuric acid gives the alkene.

Step 3: Oxymercuration-demercuration of the alkene gives the secondary acohol.

Step 4: Oxidation of the secondary alcohol using pyridinium chlorochromate gives the ketone.


Learn more about this topic:

Using Reduction to Create Primary & Secondary Alcohols
Using Reduction to Create Primary & Secondary Alcohols

from Chemistry 304: Organic Chemistry II

Chapter 1 / Lesson 6
104

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