Chapter 18: 15 P (page 694)
Classify each substituent as electron donating or electron withdrawing.

Short Answer
a. Electron donating substituents.
b. Electron withdrawing substituents.
c. Electron donating substituents.
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Chapter 18: 15 P (page 694)
Classify each substituent as electron donating or electron withdrawing.

a. Electron donating substituents.
b. Electron withdrawing substituents.
c. Electron donating substituents.
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Draw a stepwise mechanism for the following reaction.

Devise a synthesis of each compound from the indicated starting material.

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.

Draw all resonance structures for each compound and use the resonance structures to determine if the substituent has an electron-donating or electron-withdrawing resonance effect.

Rank the compounds in each group in order of increasing reactivity in electrophilic aromatic substitution: (a) ; (b) .
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