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Chapter 14: Q 39 P (page 747)

Question. The following reaction resembles the acid-catalyzed cyclization of squalene oxide. Propose a mechanism for this reaction.

Short Answer

Expert verified

Epoxide ring is highly strained due to which it readily opens up so as to release strain, thus oxygen in epoxide ring abstracts acidic proton from acid, and oxygen acquires positive charge due to which strain on ring further increases, hence it opens up and alkene carbon which is electron rich acts as a nucleophile and is present in same system thus intramolecularly attacks at carbocation generated.

Abstraction of proton and attack of nucleophile at carbocation

Step by step solution

01

Step-1. Abstraction of acidic hydrogen and ring opening of squalene oxide:

Epoxide ring is highly strained due to which it readily opens up so as to release strain, thus oxygen in epoxide ring abstracts acidic proton from acid, and oxygen acquires positive charge due to which strain on ring further increases, hence it opens up and alkene carbon which is electron rich acts as a nucleophile and is present in same system thus intramolecularly attacks at carbocation generated.

Abstraction of proton and attack of nucleophile at carbocation

02

Step-2. Attack of water as a nucleophile at carbocation and formation of product:

Water acts as a nucleophile and attacks at carbocation center, then after neutralization of positive charge on oxygen, we get our required product, that is, 3-hydroxymethyl-1-methyl-cyclopentan-1-ol.

Attack of water as a nucleophile and formation of final product

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Most popular questions from this chapter

Show how the following ethers might be synthesized using (1) alkoxymercuration-demercuration and (2) the Williamson synthesis. (When one of these methods cannot be used for the given ether, point out why it will not work.)

  1. 2-methoxybutane
  2. Ethyl cyclohexyl ether
  3. 1-methoxy-2-methylcyclopentane
  4. 1-methoxy-1-methylcyclopentane
  5. 1-isopropoxy-1-methylcyclopentane
  6. Tert-butyl phenyl ether

Show how you would use a protecting group to convert 4-bromobutan-1-ol to hept-5-yn-1-ol.

Show how you would accomplish the following transformations. Some of these examples require more than one step.

Question. Propose a complete mechanism for the reaction of cyclopentene oxide with sodium methoxide in methanol.

Question. Give the structures of the intermediates represented by letters in this synthesis.
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