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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

The following compounds are only slightly soluble in water, but one of them is very soluble in a dilute aqueous solution of sodium hydroxide. The other is still only slightly soluble.

(a) Explain the difference in solubility of these compounds in dilute sodium hydroxide.

(b) Show how this difference might be exploited to separate a mixture of these two compounds using a separatory funnel.

Predict which member of each pair has the higher boiling point, and explain the reasons for your predictions.

(a) pentan-1-ol or 3-methylbutan-1-ol

(b) pentan-2-one or pentan-2-ol

(c) pentan-2-ol or pentane-1,5-diol

(d) pentan-2-ol or heptan-2-ol

A nitro group (-NO2) effectively stabilizes a negative charge on an adjacent carbon atom through resonance:

Two of the following nitrophenols are much more acidic than phenol itself. The third compound is only slightly more acidic than phenol. Use resonance structures of the appropriate phenoxide ions to show why two of these anions should be unusually stable.

Arrange the following compounds in order of decreasing acidity.

CH3COOH CH3OH CH3CH3 CH3SO3H CH3NH2 CH3SH CH3CCH

Compounds containing deuterium (D =2H) are useful for kinetic studies and metabolic studies with new pharmaceuticals. One way to introduce deuterium is by using the reagent LiAID4, equivalent in reactivity to LiAID4. Show how to make these deuterium-labeled compounds, using LiAID4and D2Oas your sources of deuterium, and any non-deuterated starting materials you wish.

(a) CH3CHDOH (b) CH3CD2OH (c) CH3CD2OD
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