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Chapter 20: Q57 (page 812)

What ester and Grignard reagent are needed to synthesize each alcohol?

a.

b.

Short Answer

Expert verified

a.

b.

Step by step solution

01

 Step 1: Formation of tertiary alcohol from ester

Tertiary alcohol formed from an ester and a Grignard reagent must have two identical R (alkyl) groups, and this R group comes from the Grignard reagent RMgX.

All other carbons come from the ester group.

02

Preparation mechanism

(a) Alkyl 4-methylpentanoate reacts with an excess of methyl magnesium bromide in the presence of water gives the required tertiary alcohol product.

The reaction of Alkyl 4-methylpentanoate with methyl magnesium bromide

(b) Alkyl ethanoate reacts with an excess of butyl magnesium bromide in the presence of water to give the required tertiary alcohol product.

The reaction of Alkyl ethanoate with butyl magnesium bromide

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Most popular questions from this chapter

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 3600–3200cm-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

Convert propan-2-ol [CH32CHOH]into each compound. You may use any other organic or inorganic compounds

a.

b.

Draw the products of each reduction reaction.

Devise a synthesis of the given alcohol from benzene, organic alcohols having four or fewer carbons, and any needed inorganic reagents.

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.
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