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

Question

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 NaN02 and HCI at 0 degree C; 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 (+)-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 = 5.1. Oxidation of C with H2O2 (a reagent known to oxidize amino groups to nitro groups), followed by vigorous oxidation with KMn04 gives p-nitrobenzoic acid. Oxidation of 8 in a similar manner yields 1,4-benzenedicarboxylic acid (terephthalic acid), and oxidation of A yields benzoic acid. Identify compounds A, B, and C.

Explanation / Answer

From your question, it seems you don't want the answer given to you so I'll attempt to define as much as possible without giving away anything (kudos to you!). A racemic mixture means that the structure has multiple enantiomers of a chiral molecule. Basically this means that the wedges and dashes may be interchanged at certain chiral centers (a center that has multiple possibilities, each of which are not superimposable upon each other). This has to do with the formation of the molecule and how one compound reacts with another (ex. SN1 vs. E1).

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