MCAT Organic Chemistry Question — IUPAC

  • Reviewed By: Liz Flagge
  • What is the IUPAC name of the following compound: (CH3)2CH-NH-CH-(CH3)2?

    1. Diisopropylamine
    2. Diisobutylamine
    3. Di-tert-propylamine
    4. 1,1-dimethylethylamine
    Click for Explanation

    (CH3)2CH-NH-CH-(CH3)2 is the structure of a secondary amine (NH-R2), with two substituent isopropyl groups, CH(CH3)2. Acceptable names for the compound are Diisopropylamine and N-Isopropylpropan-2-amine. Diisopropylamine is used as an herbicide precursor and in vulcanization processes during the manufacture of rubber.

    A. Diisopropylamine, correct.

    B. Diisobutylamine, incorrect, The two substituent groups have 3 carbons each, isobutyl groups have four carbons, -CH2-CH-(CH3)2.

    C. Di-tert-propylamine, incorrect, There is no such thing as a tert-propyl group; the tert-butyl group requires 4 carbons.

    D. N,N-dimethylethylamine, incorrect, The IUPAC name is generated by 1) identifying the longest carbon chain (propane), 2) identifying the highest priority functional group (amine on carbon 2 of the parent propane chain, i.e. 2-amine), identify side chains (N-Isopropyl), and put it together: N-Isopropylpropan-2-amine. The structure of  N,N-dimethylethylamine is [(CH3)3]N. The ethane parent carbon chain in choice d) reveals this answer to be incorrect; the parent carbon chain in the question stem is a propane chain with three carbons.

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