Chemistry 321 Assignment 1

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Chemistry 321 Assignment 1

  1. p-Iodotoluene, when heated at 300º C in 1 M sodium hydroxide, yields two isomeric phenols. Give the structures of these two phenols and explain their formation.

  2. o-Chlorotoluene, under the same conditions as question 1, gives only a single product. Explain.

  3. Chlorobenside is a pesticide used to control red spider mites (really!). Its synthesis is shown below. Identify the structures of compounds A, B and chlorobenside itself.

  1. Fluoxetine hydrochloride (Prozac) can be made by the following route. What is the structure of Prozac? Show the reaction mechanism.

  1. Each of the following is a weaker base than aniline. Show by means of resonance forms why, in each case:

    1. acetophenone

    2. acetanilide

    3. ortho-cyanoaniline

  1. Find the structures of the following compounds and identify the amines they contain. If a structure contains more than one amine, indicate the more basic one in that compound.

    1. quinine

    2. epibatidine

    3. cocaine

    4. dendrobine

  2. Prontosil was one of the first sulfa drugs developed (for which the Nobel Prize was awarded in 1939). The structure is given below. How could it be prepared from benzene and benzene sulfonamide?

8. Look up the structure of mescaline (found in the peyote cactus). How could you prepare it from toluene and anything else you need?

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