Chapter 17: Q43P (page 895)
Predict the major product at the end of each sequence.
(a)

(b)

Short Answer
(a) 3-chlorobenzenesulfonic acid

(b) 4-chlorobenzenesulfonic acid

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Chapter 17: Q43P (page 895)
Predict the major product at the end of each sequence.
(a)

(b)

(a) 3-chlorobenzenesulfonic acid

(b) 4-chlorobenzenesulfonic acid

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What products would you expect from the following coupling reactions?
(a)

(b)

(c)

(d)

(e)

Propose mechanisms for the Birch reductions of benzoic acid and anisole just shown. Show why the observed orientation of reduction is favored in each case.
Predict the major products of the following reactions.
(a) toluene + excess CI2 (heat, pressure)
(b) benzamide ( PhCONH2 ) + Na (liquid NH3, CH3 CH2OH)
(c) o-xylene + H2 (1000 psi, 100 °C, Rh catalyst)
(d) p-xylene + Na (liquid NH3, CH3CH2OH )
(e) 
Propose a mechanism for the reaction of benzyl bromide with ethanol to give benzyl ethyl ether (shown above).
Predict the major products when the following compounds are irradiated by light and treated with (1) 1 equivalent of Br2 and (2) excess Br2.
(a) isopropylbenzene
(b) tetralin
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