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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....

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Solution Summary

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

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