Chapter 18: 27 P (page 709)
Draw all products formed when m-chlorotoluene is treated with in
Short Answer
Three possible products:


Chapter 18: 27 P (page 709)
Draw all products formed when m-chlorotoluene is treated with in
Three possible products:


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Draw the products of each reaction.


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.

In Step [2] of Mechanism 18.1, loss of a proton to form the substitution product was drawn using one resonance structure only. Use curved arrows to show how the other two resonance structures can be converted to the substitution product (PhE) by removal of a proton with: B.
You have learned two ways to make an alkyl benzene: Friedel–Crafts alkylation, and Friedel–Crafts acylation followed by reduction. Although some alkyl benzenes can be prepared by both methods, it is often true that only one method can be used to prepare a given alkyl benzene. Which method(s) can be used to prepare each of the following compounds from benzene? Show the steps that would be used.


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.

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