Vollhardt 6th Ed. (2010)
CH 21: Amines and Their Derivatives: Functional Groups Containing Nitrogen

Solutions can be seen at mendelset.com/chapters/1151


  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 # 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.

  7. Problem # 757

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