Question: Three bottles A, B. and C have been found, each of which contains a liquid and is labeled amineC8H11N. As an expert in amine chemistry,

Three bottles A, B. and C have been found, each of which contains a liquid and is labeled "amineC8H11N." 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 HCI at 0 °C; C does not. However, when the aqueous reaction mixture from the diazotizatbn of C is warmed, a gas is evolved. Compound A is optically inactive, but when it reacts with (+)-tartaric acid, two isomeric salts with different physical proper-ties are obtained. Titration of C with aqueous HCI reveals that its conjugate acid has a pKa = 5.1. Oxidation of C with H2O, (a reagent known to oxidize amino groups to nitro groups), followed by vigorous oxidation with KMnO, gives pnitrobenzoic acid. Oxidation of B in a similar manner yields 1,4-benzenedicarboxylic acid (terephthalic acid), and oxidation of A yields benzoic acid. Identify compounds A. B. and C.

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