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The question is this:

2-Phenyl-2-Butanol can be synthesized by three different combinations of a grignard reagent and a ketone. Show each combination.

I can only think of one.

  1. Butanone with Br-Mg-Ph

I can't think of anything else.

I'm not too sure if this will work:

phenylbutanone withe Br-Mg-Me

now i'm stuck. i can't think of the last one.

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  • $\begingroup$ Is a variation on the Grignard reagent acceptable, such as Ph-Mg-I? BTW, putting grignard "2-Phenyl-2-Butanol" synthesis into Google found many good references. $\endgroup$ – DrMoishe Pippik Jan 25 '15 at 5:05
  • $\begingroup$ Yeah i figured. but i'm curious if all any variation would work. Like changing Br to and I, will it affect the reaction in anyway? that's what i'm unclear about as well. that's why i tried to stick with Br. $\endgroup$ – Danxe Jan 25 '15 at 5:13
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Hint: The carbon atom bearing the OH group in the product has three substituents--phenyl, methyl, and ethyl. Any one of these groups could be introduced as a Grignard reagent, with the appropriate ketone. You have already correctly deduced one of the three possibilities.

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