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Chapter 10: Q48P (page 538)

Grignard reagents react slowly with oxetane to produce primary alcohols. Propose a mechanism for this reaction, and suggest why oxetane reacts with Grignard reagents even though most ethers do not.

Short Answer

Expert verified

When Grignard reagent reacts with oxetane, it produces primary alcohol very slowly. There is a cleavage of bonds in the oxetane ring by the Grignard reagent.A new C-C bond is formed.

Step by step solution

01

Grignard reaction with oxetane

When Grignard reagent reacts with oxetane, it produces primary alcohol very slowly. There is a cleavage of bonds in the oxetane ring by the Grignard reagent.A new C-C bond is formed.

02

 Step 2: Mechanism of oxetane with Grignard reagent

The mechanism of the Grignard reagent with oxetane is similar to epoxide cleavage in ethylene oxide by the Grignard reagent. In this, the driving force is the presence of 4-membered cyclic ether, which relieves ring strain. That is why it undergoes a Grignard reaction while most other ethers do not

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Mechanism of oxetane with Grignard reagent

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Most popular questions from this chapter

Show how you would synthesize the following alcohols by adding Grignard reagents to ethylene oxide.

  1. 2-phenylethanol
  2. 4-methylpentan-1-ol

Predict which member of each pair has the higher boiling point, and explain the reasons for your predictions.

(a) pentan-1-ol or 3-methylbutan-1-ol

(b) pentan-2-one or pentan-2-ol

(c) pentan-2-ol or pentane-1,5-diol

(d) pentan-2-ol or heptan-2-ol

Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.

  1. heptan-1-ol
  2. 1-cyclohexylethanol
  3. 1-phenylpropan-1-ol

e)

f)

Predict which member of each pair will be more soluble in water. Explain the reasons for your answers.

(a) hexan-1-ol or cyclohexanol

(b) heptan-1-ol or 4-methylphenol

(c)3-ethylhexan-3-ol or octan-2-ol

(d)hexan-2-ol or cyclooctane-1,4-diol

(e)

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
See all solutions

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