Chapter 18: 40 P (page 722)
Draw the products of each reaction.


Short Answer
a.


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Chapter 18: 40 P (page 722)
Draw the products of each reaction.


a.


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Question: Explain the reactivity and orientation effects observed in each heterocycle.

a. Pyridine is less reactive than benzene in electrophilic aromatic substitution and yields 3-substituted products.
b. Pyrrole is more reactive than benzene in electrophilic aromatic substitution and yields 2-substituted products.
Draw a stepwise mechanism for the following reaction that forms ether D. D can be converted to the antidepressant fluoxetine (trade name Prozac) in a single step.

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

Question: Ibufenac, a para-disubstituted arene with the structure HO2CCH2C6H4CH2CH(CH3)2, is a much more potent analgesic than aspirin, but it was never sold commercially because it caused liver toxicity in some clinical trials. Devise a synthesis of ibufenac from benzene and organic halides having fewer than five carbons.
How could you use ethylbenzene to prepare each compound? More than one step is required.


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