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Mistake in BR O chem Ch 1 passage 1 number 6?

Discussion in 'MCAT Study Question Q&A' started by JAH360, May 17, 2014.

  1. JAH360


    Apr 6, 2014
    The question reads: When treated with aqueous hydrochloric acid, the Grape Berry Moth sex pheromone in Figure 1 would yield:
    A. a diene
    B. an ester and an alcohol
    C. a carboxylic acid and an alcohol
    D. a carboxylic acid and an ether.

    Here is the structure of the pheromone:

    The book says the correct answer is C, and these would be the molecules it'd yield:

    But wouldn't it yield a carboxylic acid and a diol, or a carboxylic acid and 9-chlorododecanol? Doesn't dilute acid replace a double bond with an alcohol? I've typically seen double bond hydration reactions done with dilute h2so4, but HCl is a strong acid, too, and should thus yield the same products. And if that's not the case, the double bond should definitely have gone through electrophilic addition and been replaced with a chlorine... Right?
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  3. Czarcasm

    Czarcasm Hakuna matata, no worries. 2+ Year Member

    Jun 22, 2013
    Crypts of Lieberk├╝hn
    Thinking outside the box I see. ;) Provided we were considering all the possibilities, you'd be right. But unfortunately, diol wasn't one of the choices. (Plus, alkene reactions aren't tested anymore; They were removed from the AAMC outline). You'd be safe to assume they were simply asking for the initial products produced. In this case, the correct answer would be the formation of a carboxylic acid, and release an alcohol (choice C).
  4. JAH360


    Apr 6, 2014
    OK, thanks! I just wanted to make sure I wasn't going crazy, Lol.

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