Try it on paper first. A hint, the key idea and the worked solution are here when you need them.
of ethyl benzoate () is treated with a solution of methylmagnesium bromide in ether, and then with dilute acid. The product is 2-phenylpropan-2-ol (), and the yield is . Use a excess of the Grignard reagent. Find the amount of ester, the volume of the solution to measure out, and the mass of alcohol obtained. Say why the product has two methyl groups from the reagent.
Reactivity towards nucleophiles: acyl chloride > aldehyde > ketone > ester > acid > amide. NaBH reduces aldehydes and ketones, LiAlH every carbonyl group, and cold DIBAL-H takes an ester or a nitrile to the aldehyde. A Grignard reagent uses 1 equivalent on an aldehyde, ketone or nitrile and 2 on an ester or acyl chloride. One LiAlH holds 4 hydrides, and a ketone takes 1 and an ester 2. An acetal protects a carbonyl group.
Have you tried it?
Work it out on paper first. It is fine to get stuck or make a mistake: that is how we learn. When you are ready, go through the solution one step at a time, and check each step against your own.
Step 1. .
Step 2. Volume. Reagent: . Volume: .
Step 3. Alcohol. .
Step 4. Why two methyl groups. The first equivalent adds to the ester and ethoxide leaves, which gives the ketone, acetophenone. The ketone is more reactive than the ester, so a second equivalent adds to it at once. Both added groups are methyl.
Answer: , and .
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