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Chapter 10: Q17P (page 519)

Show how you would add Grignard reagents to acid chlorides or esters to synthesize the following alcohols.

  1. Ph3C-OH
  2. 3-ethyl-2-methylpentan-3-ol
  3. dicyclohexylphenylmethanol

Short Answer

Expert verified

a.

b.

c.

Step by step solution

01

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.

02

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

03

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

04

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.

Synthesis of alcohol

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Most popular questions from this chapter

Give systematic (IUPAC) names for the following diols and phenols.

Often, compounds can be synthesized by more than one method. Show how this 3° alcohol can be made from the following:

(a) two different ketones

(b) two different alkenes

(c) an ester

(d) a 3° alkyl bromide

Question: Show two ways you could synthesize each of the following secondary alcohols by adding an appropriate Grignard reagent to an aldehyde.

a.

b.

c.

Arrange the following compounds in order of decreasing acidity.

CH3COOH CH3OH CH3CH3 CH3SO3H CH3NH2 CH3SH CH3CCH

Show how you would synthesize the following:

  1. 2-phenylethanol by the addition of formaldehyde to a suitable Grignard reagent
  2. 2-phenylethanol from a suitable alkene
  3. cyclohexylmethanol from an alkyl halide using an SN2 reaction
  4. 3-cyclohexylpropan-1-ol by the addition of ethylene oxide to a suitable Grignard reagent
  5. cis-pent-2-en-1-thiol from a suitable alkenyl halide
  6. 2,5-dimethylhexane from a four-carbon alkyl halide
See all solutions

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