Loudon 5th Ed. (2009)
CH 18: The Chemistry of Aryl Halides, Vinylic Halides, and Phenols. Transition-Metal Catalysis

Solutions can be seen at mendelset.com/chapters/834


  1. Problem # 305

    Rank each group of acids in order of decreasing acidity. (1 = most acidic)

    Explain your reasoning. You will have to use more than one rule in your explanation (resonance, electronegativity, atomic radius, etc.). 

     

  2. Problem # 611

    Draw in the arrows to show the electron flow and resonance forms in the nucleophilic aromatic substitution reaction below.

    Note: Depending on the textbook, nucleophilic aromatic substitution is referred to as NAS, SNAr, or addition-elimination.

     

  3. Problem # 612

    Draw a mechanism for the nucleophilic aromatic substitution (SNAr) reaction below. Show all resonance forms of the intermediate.

  4. Problem # 615

    Let's go through a benzyne reaction (also called elimination-addition).

    In the reaction below, the strong base (NaNH2) will form a benzyne intermediate, which when forms either ortho nitroaniline or meta nitroaniline.

    Used curved arrows to show the formation of each intermediate and the final products.

  5. Problem # 616

    Let's go through another way to make benzyne.

    First, let's form a Grignard reagent. Then, let's elminate to form benzyne.