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Synthesis of 3-methyl-3-pentanol

  1. Nov 14, 2011 #1
    1. The problem statement, all variables and given/known data
    A student wants to synthesize 3-methyl-3-pentanol. They react 2.3 equivalents of ethyl magnesium bromide with ethyl acetate, and then quench the reaction with sulfuric acid.

    1. what is the product of the dimerization reaction?
    2. What is the product from the reaction of ethyl magnesium bromide and water?
    3. What two side products can potentially form from quenching the 3-methyl-3-pentoxide magnesium bromide salt with hydrochloric acid?
    4. What can we use to quench the reaction to eliminate the formation of one of these products? Explain.
    5. A student can't find any ethyl acetate, and decides to use acetic acid instead. Upon addition of acetic acid, he observes a vigorous reaction and he quenches his reaction with sulfuric acid. What product(s) are formed in this reaction?
    6. Show a purification scheme for the reaction described in the problem statement.
    2. Relevant equations

    3. The attempt at a solution
    1. So here, I think I am determining what the product is when ethyl magnesium bromide reacts with ethyl magnesium bromide. Is it butane?
    2. Ethyl magnesium bromide + water -> propane + Mg(OH)Br?
    3. Not sure here.
    4. Maybe HCl?
    5. I don't know where to start.
    Last edited: Nov 14, 2011
  2. jcsd
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