Chapter 18: 11 P (page 690)
Intramolecular reactions are also observed in Friedel–Crafts alkylation. Draw the intramolecular alkylation product formed from each of the following reactants. (Watch out for rearrangements!)
Chapter 18: 11 P (page 690)
Intramolecular reactions are also observed in Friedel–Crafts alkylation. Draw the intramolecular alkylation product formed from each of the following reactants. (Watch out for rearrangements!)
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Get started for freeDraw all resonance structures for the carbocation formed by ortho attack of the electrophile on each starting material. Label any resonance structures that are especially stable or unstable.
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.
D is an intermediate in the synthesis of rosiglitazone (trade name Avandia), a drug used for type 2 diabetes. Suggest two different methods to prepare the ether in D by substitution reactions.
Which of the following compounds undergo Friedel–Crafts alkylation with and ? Draw the products formed when a reaction occurs.
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