Question

Question 9 of 22 Organic Chemistry Mapes Three bottles A, B, and C have been found, each of which contains a liquid and is labeled "amine CotN. 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 HCl at 0 ℃: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 properties are obtained. Titration of C with aqueous HCl reveals that its conjugate acid has a pk.-5.1.Oxidation of C with H202 (a reagent known to oxidize amino groups to nitro groups), followed by H2 vigorous oxidation with KMnOs gives p-nitrobenzoic acid. Oxidation ur response for 6 would not give off a gas of 8 in a similar manner yields 1,4-benzenedicarboxylic acid (terephthalic acid), and oxidation of A yields benzoic acid. Identify pon oxidat compounds A. B, and C at o C Nitrous acid at 0"C tests for alkylamines Likewise, your structure upon oxidation, yield peaminobenzoic acid rather than 1.4 xylic acid H2 O Previous Try Agan Next Exit

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Answer 1

NH-CH3 N-o CH3 NaNO2/HC H3 nitrosoamine 0-5 degC 2 CH2NH2 CH2 B NaNO2/HIO CH3 0-5 degC CH2CH2NH2 NaNO2/HCI CH2CH2 + N2 +CI 0-5 degC

CH2CH2NHOC-CHCH-COOH OH OH OH OH L(+) tartaric acid CH2CH2NH2 +HOOC-CH-CH-COOH OH OH

Cl- NHCH3 HCL NH 2CH3 CH3 CH3