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Chapter 17: Q27E (page 567)

Epoxides react with Grignard reagents to yield alcohols. Propose a mechanism.

Short Answer

Expert verified

The mechanism followed as:

Step by step solution

01

Reaction of epoxide with Grignard reagent

Epoxide on reaction with Grignard reagent opens as an electrophile on the addition of the alkyl group of the Grignard reagent, and the formation of alcohol occurs.

The hydroxyl group and the alkyl group of the Grignard reagent have trans relations with each other.

02

Reaction of given epoxide with Grignard reagent

The given epoxide reacts with the methyl magnesium bromide to form the intermediate called alkoxide because oxygen has a negative charge, followed by hydrolysis so that the negatively charged oxygen gains the proton, and hydroxyl formation occurs.

03

Mechanism

React with methyl magnesium bromide
Alkoxide formation
Hydrolysis

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Most popular questions from this chapter

What carbonyl compounds would you reduce to prepare the followingalcohols? List all possibilities.

(a)

(b)

(c)

A compound of unknown structure gave the following spectroscopic data:

Mass spectrum: $M^{+} = 88.1$

IR: $3600 {cm}^{- 1}$

$^{1} H$ NMR: 1.4 $δ$ (2H, quartet, J=7Hz); 1.2 $δ$ (6H, singlet); 1.0 $δ$ (1H, singlet); 0.9 $δ$ (3H, triplet, J=7Hz)

${^{1}}^{3} C$ NMR: 74, 35, 27, 25 $δ$

(a) Assuming that the compound contains C and H but may or may not contain O, give three possible molecular formulas.

(b) How many protons (H) does the compound contain?

(c) What functional group(s) does the compound contain?

(d) How many carbons does the compound contain?

(e) What is the molecular formula of the compound?

(f) What is the structure of the compound?

(g) Assign peaks in the molecule’s NMR spectrum corresponding to specific protons.

Testosterone is one of the most important male steroid hormones. When testosterone is dehydrated by treatment with acid, rearrangement occurs to yield the product shown. Propose a mechanism to account for this reaction.

Phenols generally have lower pKa’s than aliphatic alcohols because of resonance stabilization with the aromatic ring. Draw all of the resonance contributors for the phenolate ions below. Make note of how the substituents either stabilize or destabilize the system.

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Propose a mechanism to account for the formation of ethyl acetate. Take into account the reversible reaction between aldehydes and alcohols:

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