MS 934 - Carey and Giuliano 8th Ed. CH 19

MS 934 - Carey and Giuliano 8th Ed. CH 19

Textbook and Chapter: Carey and Giuliano 8th Ed. (2010), Chapter 19

Keyword: nucleophilic acyl substitution

Description: Goes over carboxylic acid derivatives and the nucleophilic acyl substitution mechanism. Includes synthesis problems.

Total Problems: 6

  1. Problem # 726

    Show two esters that would yield the two alcohols below after treatment with lithium aluminum hydride.

  2. Problem # 727

    Show how the ester below can be prepared from propene.

  3. 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.

  4. Problem # 729

    The ester below was dissolved in a solution of water, a small amount of which was isotopically labeled with O-18, denoted with an asterisk.

    After a few hours, some isotopically labeled oxygen was found in the ester. Where was it found in the ester? Can you explain why?

  5. Problem # 730

    N,N-dimethylformamide (DMF) is shown below. Based on its structure, you might expect to see only one -CH3 signal in the 1H NMR spectrum. But instead DMF shows two different -CH3 signals. Explain.

  6. Problem # 735

    Show how each ketone below can be prepared from sodium cyanide and either ethylene or propene.

    You may also use methyl Grignard and ethylene oxide.