Chapter 17: Q48P (page 898)
Starting from toluene, propose syntheses for ortho-, meta-, and para-chlorobenzoic acid.
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Chapter 17: Q48P (page 898)
Starting from toluene, propose syntheses for ortho-, meta-, and para-chlorobenzoic acid.



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(a) Based on what you know about the relative stabilities of alkyl cations and benzylic cations, predict the product of addition of HBr to 1-phenylpropene.
(b) Propose a mechanism for this reaction.
(c) Based on what you know about the relative stabilities of alkyl radicals and benzylic radicals, predict the product of addition of HBr to 1-phenylpropene in the presence of a free-radical initiator.
(d) Propose a mechanism for this reaction.
Show how you would use Suzuki reactions to synthesize these products from the indicated starting materials. You may use any additional reagents you need.

In Chapter 14, we saw that Agent Orange contains (2,4,5-trichlorophenoxy) acetic acid, called 2,4,5-T. This compound is synthesized by the partial reaction of 1,2,4,5-tetrachlorobenzene with sodium hydroxide, followed by a reaction with sodium chloroacetate, ClCH2CO2Na.
(a) Draw the structures of these compounds, and write equations for these reactions.
(b) One of the impurities in the Agent Orange used in Vietnam was 2,3,7,8-tetrachlorodibenzodioxin (2,3,7,8-TCDD), often incorrectly called 鈥渄ioxin.鈥 Propose a mechanism to show how 2,3,7,8-TCDD is formed in the synthesis of 2,4,5-T.
(c) Show how the TCDD contamination might be eliminated, both after the first step and on completion of the synthesis

Predict the major products of treating the following compounds with hot, concentrated potassium permanganate, followed by acidification with dilute HCl.
(a) isopropylbenzene
(b) p-xylene
(c) tetralin
Propose products (if any) and mechanisms for the following AICI3-catalyzed reactions:
猞 chlorocyclohexane with benzene
猞 methyl chloride with anisole
猞 3-chloro-2,2-dimethylbutane with isopropylbenzene
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