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Acetone cannot be obtained from
A.Hydrolysis of isopropylidene chloride
B.Hydration of propyne
C.Dehydrogenation of isopropyl alcohol
D.Hydrolysis of ester

Last updated date: 20th Jun 2024
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Hint:Acetone is also called 2-propanone or dimethyl ketone, an organic solvent of industrial and chemical significance. It is the simplest and most important of the aliphatic ketones. Pure acetone is usually found colourless, harmless, aromatic, flammable. The cumene hydroperoxide process is a dominant process used in the commercial production of acetone

Complete step by step answer:
Acetone can be obtained from modifications of all the reactions in A, B, and C. But Acetone cannot be obtained from the transformation in D.
-Hydrolysis of isopropylidene chloride gives propane $ - 2,2 - $ diol, and it loses a molecule of water to form acetone.
-Hydration of propyne in the presence of $HgS{O_4}$ and ${H_2}S{O_4}$ gives acetone. Hydration of alkynes begins very similar to the hydration of alkenes through the addition of the first water molecule. -Although, this first hydration reaction forms an enol, alcohol bonded to a vinyl carbon. Enols instantly undergo a special type of isomerization reaction called tautomerization to form carbonyl groups - aldehydes or ketones. To keep things simple, this reaction is termed as "enol-keto" tautomerization with the understanding that aldehydes form on terminal alkyne carbons. As with alkenes, hydration (addition of water) to alkynes usually requires a strong acid, usually sulfuric acid with a mercuric sulfate catalyst.
-Dehydrogenation (oxidation) of isopropyl alcohol in the presence of the acidified potassium dichromate usually gives out acetone. The secondary alcohols are usually oxidized to ketones. For example, if you heat the secondary alcohol propan$ - 2 - $ol with sodium or potassium dichromate (VI) solution acidified with dilute sulfuric acid, propanone will be formed.
-Hydrolysis of ester is the splitting or dividing them into carboxylic acids and alcohols with the help of water, dilute acid or alkali. So acetone cannot be produced from hydrolysis of esters.
Thus correct answer is option D.

-Ester hydrolysis is a reaction which breaks an ester bond with a molecule of water or a hydroxide ion to form carboxylic acid and an alcohol. One common use of ester hydrolysis is creating soaps, which are the salts of fatty acids of triglycerides. This process is known as saponification.
-Acid hydrolysis is simply reverse of esterification.