Three bottles A, B, and C have been found, each of which contains a liquid and is

Chapter 23, Problem 23.64

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Three bottles A, B, and C have been found, each of which contains a liquid and is labeled amine C8H11N. As an expert in amine chemistry, you have been hired as a consultant and asked to identify each compound. Compounds A and B give off a gas when they react with NaNO2 and HCl at 0 8C; C does not. However, when the aqueous reaction mixture from the diazotization of C is warmed, a gas is evolved. Compound A is optically inactive, but when it reacts with (1)-tartaric acid, two isomeric salts with different physical properties are obtained. Titration of C with aqueous HCl reveals that its conjugate acid has a pKa 5 5.1. Oxidation of C with H2O2 (a reagent known to oxidize amino groups to nitro groups), followed by vigorous oxidation with KMnO4, gives p-nitrobenzoic acid. Oxidation of B in a similar manner yields 1,4- benzene dicarboxylic acid (terephthalic acid), and oxidation of A yields benzoic acid. Identify compounds A, B, and C.