Q17P Show how you would add Grignard ... [FREE SOLUTION]

Chapter 10: Q17P (page 519)

Show how you would add Grignard reagents to acid chlorides or esters to synthesize the following alcohols.
Ph₃C-OH
3-ethyl-2-methylpentan-3-ol
dicyclohexylphenylmethanol

Short Answer

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Step by step solution

Alcohols from acid chlorides

Acid chlorides, when added to the Grignard reagent, it forms ketone. Then again, the Grignard reagent is added, and the last step is hydrolysis.This reaction results in tertiary alcohol.

Alcohol synthesis in (a)

a. In this reaction, 2 Equiv. of Grignard reagent (PhMgBr) is added to acid chloride. It forms ketone, and on further hydrolysis, it results in tertiary alcohol.

Synthesis of alcohol

Alcohol synthesis in (b)

b. In this reaction, 2 Equiv. of Grignard reagent ( ) is added to acid chloride. It forms ketone, and on further hydrolysis, it results in tertiary alcohol. Here, acid chlorides work as a starting material.

Synthesis of alcohol

Alcohol synthesis in (c)

c. In this reaction, 2 Equiv. of Grignard reagent ( ) is added to acid chloride. It forms ketone, and on further hydrolysis, it results in tertiary alcohol. Here, acid chlorides work as a starting material.