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Chapter 10: Q16P (page 519)

Propose a mechanism for the reaction of acetyl chloride with phenylmagnesium bromide to give 1,1-diphenylethanol.

Short Answer

Expert verified

When acid chloride is added to 2 equivalents of Grignard reagent in an ether solvent, and after protonation, it forms tertiary alcohol. In acid chlorides, the OH group of the acid is replaced by a Cl atom.

Step by step solution

01

Addition of acid chloride to Grignard reagent

When acid chloride is added to 2 equivalents of Grignard reagent in an ether solvent, and after protonation, it forms tertiary alcohol. In acid chlorides, the OH group of the acid is replaced by a Cl atom.

02

Mechanism for the reaction between an acid chloride and phenylmagnesium bromide

The mechanism shows the nucleophilic substitution, and Cl is the leaving group. It takes place at carbonyl carbon, which is the unusual feature we see in this mechanism.

Mechanism of reaction between an acid chloride and Grignard reagent

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Most popular questions from this chapter

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

(a) two different ketones

(b) two different alkenes

(c) an ester

(d) a 3掳 alkyl bromide

Give IUPAC names for the following compounds.

a.

b.

c.

Arrange the following compounds in order of decreasing acidity.

CH3COOH CH3OH CH3CH3 CH3SO3H CH3NH2 CH3SH CH3CCH

Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.

(a) 1-methylcyclohexanol (b) cyclohexylmethanol

(c) 1-(hydroxymethyl)cyclohexanol (d) trans-2-methylcyclohexanol

(e) 2-chloro-1-methylcyclohexanol (f) 1-(phenylmethyl)cyclohexanol

For each synthesis, start with bromocyclohexane and predict the products. Assume that an excess of each reactant is added so that all possible reactions that can happen will happen.
See all solutions

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