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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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Most popular questions from this chapter

Question: The bicyclic heterocycles quinoline and indole undergo electrophilic aromatic substitution to give the products shown.

a. Explain why electrophilic substitution occurs on the ring without the N atom for quinoline, but occurs on the ring with the N atom in indole.

b. Explain why electrophilic substitution occurs more readily at C8 than C7 in quinoline.

c. Explain why electrophilic substitution occurs more readily at C3 rather than C2 of indole.

Question: Use the reactions in this chapter along with those learned in Chapters 11 and 12 to synthesize each compound. You may use benzene, acetylene, two-carbon alcohols, ethylene oxide and any organic reagents.

d.

Why is benzene less reactive toward electrophiles than an alkene, even though it has more π electrons than an alkene (six versus two)?

Rank the following compounds in order of increasing reactivity in electrophilic aromatic substitution.

Draw the products of each reaction.
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