Propose a structure for the carboxylic acid, C7H14O2, with the following 13C and DEPT NMR data: 185.4 (4°), 42.9 (2º), 42.2 (4°), 25.0 (1), 18.2 (2º), 14.5 (1°) ppm.

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Rank the following compounds in order of increasing basicity and explain the order you chose.

Deduce the structure of an unknown compound using the data. C,H,O: 10 NMR: 8 9.8 (1 H, s), 8 1.1 (9 H, s)

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When an α-hydroxy amide is treated with Br2 in aqueous NaOH under Hofmann rearrangement conditions, loss of CO2 occurs and a chain-shortened aldehyde is formed. The mechanism involves the following steps: Base abstracts an acidic amide proton, yielding amide anion 1; The amide anion reacts with bromine in an α-substitution reaction to give N-bromoamide 2. Abstraction of the remaining amide proton by base gives a resonance-stabilized bromoamide anion 3; Rearrangement occurs to yield isocyanate 4; Water adds to the isocyanate to yield carbamic acid 5; Elimination of CO2 yields carbinolamine 6; Following proton transfer, expulsion of ammonia yields the final product aldehyde. Write out the mechanism and then draw the structures of bromoamide anion 3 and amide anion 1.