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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

Give IUPAC names for the following compounds.

a.

b.

c.

Give a systematic (IUPAC) name for each alcohol. Classify each as primary, secondary, or tertiary.

Vinyl alcohols are generally unstable, quickly isomerizing to carbonyl compounds. Propose mechanisms for the following isomerizations.

(a)

(b)

c)

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

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.
See all solutions

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