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Chapter 20: Q81 (page 816)

Draw a stepwise mechanism for the following reaction of a Grignard reagent with a cyclic amide.

Short Answer

Expert verified

Grignard reaction occurs when the alkyl part of the Grignard reagent attacks at the carbonyl carbon. Subsequently, the hydrolysis forms the substituted alcohol.

The excess Grignard reagent substitutes another alkyl group via the bimolecular substitution reaction.

Step by step solution

01

Grignard reaction

Grignard reaction occurs when the alkyl part of the Grignard reagent attacks at the carbonyl carbon. Subsequently, the hydrolysis forms the substituted alcohol.

The excess Grignard reagent substitutes another alkyl group via the bimolecular substitution reaction.

02

Explanation

In the first step, the anion part of the ethyl magnesium bromide attacks at the carbonyl carbon followed by the hydrolysis.

In the second step, the other ethyl magnesium bromide molecule attacks at the alcoholic carbon and eliminates the hydroxide ion.

The mechanism is shown as:

Grignard reaction mechanism

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Most popular questions from this chapter

Reaction of benzyl magnesium chloride with formaldehyde yields alcohols N and P after protonation. Draw a stepwise mechanism that shows how both products are formed.

Treatment of compound E (molecular formula C4H8O2 ) with excessCH3CH2MgBr yieldscompound F (molecular formula C6H14O) after protonation withH2O . E shows a strongabsorption in its IR spectrum at 1743cm-1. F shows a strong IR absorption at 3600鈥�3200cm-1.The H1NMR spectral data of E and F are given.

What are the structures of E and F?

Compound E signals at 1.2 (triplet, 3 H), 2.0 (singlet, 3 H), and 4.1 (quartet, 2 H) ppm

Compound F signals at 0.9 (triplet, 6 H), 1.1 (singlet, 3 H), 1.5 (quartet, 4 H), and 1.55(singlet, 1 H) ppm

Draw the products of the following reactions with organometallic reagents.

Treatment of compound C (molecular formula C4H8O) with C6H5MgBr, followed by H2O, affords compound D (molecular formula C10H14O). Compound D has a strong peak in its IR spectrum at 3600鈥�3200 cm-1. The H1 NMR spectral data of C and D are given. What are the structures of C and D?Compound C signals at 1.3 (singlet, 6 H) and 2.4 (singlet, 2 H) ppm Compound D signals at 1.2 (singlet, 6 H), 1.6 (singlet, 1 H), 2.7 (singlet, 2 H), and 7.2 (multiplet, 5 H) ppm

Draw a stepwise mechanism for the following reaction of a Grignard reagent with a cyclic amide.
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