Explore BrainMass
Share

Explore BrainMass

    Organic Synthesis : Identify the Products Word Problem

    This content was COPIED from BrainMass.com - View the original, and get the already-completed solution here!

    Please see the attached file for the fully formatted problems.

    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....

    © BrainMass Inc. brainmass.com October 9, 2019, 10:21 pm ad1c9bdddf
    https://brainmass.com/chemistry/organic-reactions/organic-synthesis-identify-the-products-word-problem-217299

    Attachments

    Solution Summary

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

    $2.19