Try it on paper first. A hint, the key idea and the worked solution are here when you need them.
A chemist reduces of methyl 4-oxopentanoate, which has one ketone group and one ester group, with lithium aluminium hydride. The ketone takes one hydride ion. The ester takes two. Each holds four hydride ions, and its molar mass is . Find the hydride ions needed for each molecule, the least amount of in millimoles and the least mass. Name the organic product after dilute acid is added.
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. Ketone 1, ester 2: hydride ions for each molecule.
Step 2. Total hydride ions: . Each gives 4, so .
Step 3. Mass: .
Step 4. The product. Both groups are reduced: the ketone to a secondary alcohol, and the ester to a primary alcohol and methanol. The product is pentane-1,4-diol.
Answer: 3, and .
Watch out. In practice a chemist uses an excess, because the reagent also reacts with traces of water.
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