PROBLEM 10.65 Question: Devise a synthesis of ... [FREE SOLUTION]

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Chapter 10: PROBLEM 10.65 (page 424)

Question: Devise a synthesis of each compound from cyclohexene as the starting material. More than one step is needed.
a.
b.
c.
d.

Short Answer

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Answer

Step by step solution

Epoxide

Epoxides are formed from alkenes by the attack of the OH group on the carbon containing the leaving group

Nucleophiles

Nucleophiles directly attack the carbon that contains the leaving group and form the desired product.

Explanation

a. The given epoxide is formed by the alkene in the following way:

Chlorination occurs on the alkene in the presence of water to form an epoxide by intramolecular S_N2 mechanism.

Formation of epoxide

b. The given product is formed by the alkene in the following way:

The alkene reacts with HBr. The product then undergoes S_N2 attack by the cyanide ion and forms the desired product.

Formation of the product

c. The given product is formed by the alkene in the following way:

The alkene reacts with HBr. The product then undergoes S_N2 attack by the hydroxide ion. The product cyclohexanol undergoes proton abstraction by the base NaH and attacks propyl iodide.

Formation of the productd. The formation of epoxide is similar to part a. The epoxide is then attacked by the nucleophile HS^- , followed by water, and it forms the desired product.