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Organic Chemistry - Alcohol Synthesis Problem

  1. Dec 4, 2013 #1
    I have attached a file of the alcohol I need to synthesize and my futile attempt... I was thinking of using a hydration reaction to make the alcohol from the alkyne group. So basically I would mix the alkyne group with H2O and some how produce the alcohol group.

    Am I heading in the right direction?

    Attached Files:

  2. jcsd
  3. Dec 4, 2013 #2
    It's been a while since I've done Ochem, but here's my suggestion. Hydrate the alkyne, substitute a hydroxyl group with a halide using an equimolar amount of a selective halide salt, like PBr3. The resulting aklene will be on the 1,2 position, and a antimarkovnikov addition of an alcohol should add an alcohol onto the 1 position, creating your desired substance.

    By the way, you drew the alkyne incorrectly. It's always drawn in a straight line due to sp hybridization.

    EDIT: Actually, what I said was wrong. I was thinking about it on the way to class, removal of the halide will result in the 2,3 alkene, the hydrogen on carbon 2 (the one with the hydroxyl group) will be removed. I'll think about this more.
    Last edited: Dec 5, 2013
  4. Dec 6, 2013 #3

    STEP 1: convert the alkyne to an alkene using Na/liq.NH3 .
    STEP 2: Use NBS(N-Bromosuccinimide) to get allyl bromide(CH3CH=CHCH2Br) which when reacted with aq.NaOH gives alcohol(CH3CH=CHCH2OH).
    STEP 3: Acidic hydrolysis of this alcohol gives the required product.

  5. Dec 7, 2013 #4


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    You're looking to form 1, 3 - butanediol I believe. I'm pretty sure you can mix an alkene with water to get an alcohol.

    My organic chem is a bit rusty, but I believe (1 - hydroxy - 2 - butene) + H - OH should give you what you're looking for.
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