High School

Given a Grignard reagent, draw a ketone that can be used to produce each of the following compounds:

a) 3-methyl-3-pentanol
- Grignard reagent: MeMgBr
- Ketone:

b) 1-ethylcyclohexanol
- Grignard reagent: EtMgBr
- Ketone:

c) Triphenylmethanol
- Grignard reagent: PhMgBr
- Ketone:

Answer :

A Grignard reagent, named after the French chemist Victor Grignard, is a chemical compound containing a carbon-magnesium bond.

It is highly reactive and is often used in the formation of carbon-carbon bonds, making it very useful in organic chemistry.

Now, let's determine the ketones needed to produce the given compounds using the specified Grignard reagents.

a) To produce 3-methyl-3-pentanol using the Grignard reagent methylmagnesium bromide (MeMgBr), the ketone needed would be pentan-2-one.

In this reaction, the Grignard reagent would attack the carbonyl carbon of the ketone, leading to the alcohol product after a subsequent acid workup.

b) In order to form 1-ethylcyclohexanol using ethylmagnesium bromide (EtMgBr), you would need the ketone cyclohexanone.

Here, the Grignard reagent would add to the carbonyl carbon of the ketone, yielding the desired alcohol after an acid workup.

c) To make triphenylmethanol using phenylmagnesium bromide (PhMgBr), the ketone benzophenone would be necessary.

This is a bit different from the previous examples because this Grignard reagent would attack twice (it is used in excess), adding two phenyl groups to the ketone's carbonyl carbon and forming the tertiary alcohol triphenylmethanol after an acid workup.

Remember, in these reactions, it's important to keep the Grignard reagent and the ketone away from any water or acid until the final step, as the Grignard reagent is highly reactive and will readily react with any proton source.

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