Carey and Giuliano 8th Ed. (2010)
CH 21: Amines

Solutions can be seen at mendelset.com/chapters/285


  1. Problem # 584

    Imidazole (shown below) has two nitrogen atoms, N-1 and N-3. Which nitrogen is more basic?

    To answer this problem, draw the product after each nitrogen protonates, and compare their stabilities. Explain your reasoning.

  2. Problem # 728

    The acyl group is a protecting group for amines. Amines can be acylated using acetic anhydride, and deacylated with base.

    Propose a mechanism for each reaction.

  3. Problem # 752

    Rank the amines A through D below in order of decreasing basicity (1 = most basic). Explain your reasoning.

  4. Problem # 753

    Rank the amines W through Z below in order of decreasing basicity (1 = most basic). Explain your reasoning.

  5. Problem # 754

    Show how each amine can be prepared from a carbonyl and an amine via reductive amination.

  6. Problem # 755

    The nitrosyl cation is shown below. Also shown are several proposed resonance arrows, only one of which is correct.

    Draw the resonance forms that would follow from each set of arrows, and include formal charges. Which one is the correct resonance form? Explain your reasoning.

  7. Problem # 756

    For each amine below, show all Hofmann elmination products.

    If more than one product is formed, predict which one will be the major product.

  8. Problem # 757

    Propose a synthesis to accomplish each transformation. The only carbon sources allowed are alkenes and NaCN.