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Dolbier HW Solutions 291 - 285 REACTIONS OF ARENES...

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12.19 A straightforward approach to the synthesis of m -nitrobenzoic acid involves preparation of ben- zoic acid by oxidation of toluene, followed by nitration. The carboxyl group of benzoic acid is meta-directing. Nitration of toluene prior to oxidation would lead to a mixture of ortho and para products. 12.20 The text points out that C-1 of naphthalene is more reactive than C-2 toward electrophilic aromatic substitution. Thus, of the two possible products of sulfonation, naphthalene-1-sulfonic acid should be formed faster and should be the major product under conditions of kinetic control. Since the problem states that the product under conditions of thermodynamic control is the other isomer, naphthalene-2-sulfonic acid is the major product at elevated temperature. Naphthalene-2-sulfonic acid is the more stable isomer for steric reasons. The hydrogen at C-8 (the one shown in the equation) crowds the group in naphthalene-1-sulfonic acid. 12.21
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