EAS - practice problems - key

EAS - practice problems - key - Practice problems for...

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Practice problems for Reactions of Arenes (Ch 15) Chem 345 - Yoon 1 . CH 3 CH 3 H 3 C CH 3 H O S O O OH CH 3 CH 3 CH 3 CH 3 H HO S O O O Cl CH 3 H 3 C Al Cl Cl Cl CH 3 H CH 3 H 3 C H 2. a. Naphthalene has several degrees of symmetry, so there are only two chemically distinct hydrogens (labeled on the structure to the right as H α and H β ). Substitution at any of the H α ’s leads to the same product; substitution at any of the H β ’s leads to a second product. We’ll consider substitution at each of these two positions. b. H α : Br + H Br H Br H Br H Br H Br H β : Br + Br H Br H Br H Br H Br H c. Attack of Br + at either H α or H β leads to a cationic intermediate where the positive charge is delocalized over five carbons. Note that the intermediate that arises from attack at H α has two resonance structures where the left-hand ring is still aromatic; there is no aromatic character to the other three resonance structures. On the other hand, attack at H β
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This document was uploaded on 10/09/2008.

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EAS - practice problems - key - Practice problems for...

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