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Chapter 18: Q 77. (page 728)

Question: Draw a stepwise mechanism for the following intramolecular reaction, which is used in the synthesis of the female sex hormone estrone.

Short Answer

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Answer

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01

Intramolecular cyclization

Intramolecular cyclization occurs when a compound is nucleophile (double bond, or groups containing lone pair of electrons) and electrophile (C=O, C-X, carbocations).

02

Explanation

The mechanism involves the abstraction of a proton from the given reagent.

The second step involves dehydration.

The third step involves intramolecular cyclization due to the presence of alkene and carbocation in the vicinity.

Synthesis of female sex hormone

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