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Chapter 13: Q 40. (page 522)

Question:Like alcohols, ethers undergo 伪 cleavage by breaking a carbon鈥揷arbon bond between an alkyl group and the carbon bonded to the ether oxygen atom; that is, the red C鈥揅 bond in R鈥�CH2OR'is broken. With this in mind, propose structures for the fragments formed by 伪 cleavage of(CH3)2CHCH2OCH2CH3. Suggest a reason why an ether fragments by 伪 cleavage.

Short Answer

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Answer

Resonance stabilization favors fragmentation.

Step by step solution

01

Step 1: α-cleavage of ethers

伪-cleavage of ethers occurs between the C-C bond that is adjacent to the ether oxygen. The cleavage results in the formation of an alkyl radical and a resonance-stabilized carbocation containing the oxygen atom. The reaction is given below.

伪-cleavage of ether

02

Step 2: α-cleavage of  (CH3)2CHCH2OCH2CH3

The 伪-cleavage of the given ether occurs in two ways, as shown below.

伪-cleavage of the given ether

Ethers can form fragments via伪-cleavage because of the formation of the resonance-stabilized carbocations, which acts as the driving force for the cleavage to occur.

The resonance-stabilized structures of the two carbocations formed upon cleavage of the above ether are given below.

Resonance stabilization of the carbocations

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