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Organic Synthesis : Identify the Products Word Problem

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10. A compound C10H13NO (A) has the following 1H NMR spectrum:
delta (ppm) Integration Multiplicity
7.4-7.2 4H multiplet
3.2 3H singlet
2.3 3H singlet
1.8 3H singlet
Compound A was insoluble in 5% aqueous HCl, but dissolved slowly on heating with aqueous sodium hydroxide. This reaction mixture was cooled and carefully acidified. Distillation of this mixture gave a volatile acidic liquid (B) which smelled like vinegar. This material was titrated and found to have a molecular weight of 60 ±I. The residue from the distillation of B was made alkaline, and from this solution a basic substance Compound C (C8H11N) was obtained. Treatment of C with excess benzenesulphonyl chloride in alkaline solution gave a solid (D), which was insoluble in acid. Compound C was subjected to high pressure hydrogenation to give Compound E (C8H17N). Treatment of E with excess methyl iodide followed by heating with silver oxide gave trimethylamine and 3- methylcyclohexene.
Give structures for A, B, C, D, and E. Show your reasoning and reaction equations.

12. Show plausible mechanisms for the following....


Solution Summary

Easy stepwise explanation to elucidate structure of compounds using given spectroscopic data as well as reaction mechanisms