Question

A keto ester (X) with molecular formula ${{C}_{6}}{{H}_{10}}{{O}_{3}}$on treatment with NaOH and ${{I}_{2}}$ does not give iodoform but on boiling with dilute KOH gives a compound (Y) with molecular formula ${{C}_{4}}{{H}_{5}}{{O}_{3}}K$which upon acidification followed by heating undergoes decarboxylation to give acetone. The keto ester (X) is?
A.$C{{H}_{3}}COC{{H}_{2}}C{{H}_{2}}COOC{{H}_{3}}$
B.$C{{H}_{3}}COC{{H}_{2}}COO{{C}_{2}}{{H}_{5}}$
C.$C{{H}_{3}}C{{H}_{2}}OC{{H}_{2}}COOC{{H}_{3}}$
D.$C{{H}_{3}}COCH(C{{H}_{3}})COOC{{H}_{3}}$

Answer 1

Hint: Before answering this question, we should first know about keto esters. Keto esters are a type of exogenous ketones which could be taken orally. It is used to minimize the ketosis effects. In our body, firstly the carbohydrates are burned down by our body, and then the fat as soon as the carb stores are depleted.

Complete answer:
Our body starts to burn stored fat to gain energy once the body enters ketosis. Ketosis could be achieved by fasting or by limiting the intake of carbohydrates. The ketogenic diet is in fashion nowadays, it helps to limit the carbs intake which helps to burn fat rather than carbohydrates for energy.
There is only one type of keto ester that is commercially available i.e D-Beta Hydroxybutyrate/D 1,3- butanediol. It can be derived naturally by the process of fermentation. Dr. Richar Veech created it from NIH and it was commercialized with HVMN and ketoneaid, It is a silicon valley based technology company.
Betahydroxhybutyric acid that is found in ketone salts is linked by monoester and linked with 1,3-butanediol rather than bases. Some of this ketone body is directly metabolized and others by the liver. There are some other ketones like acetoacetate. It is a diester that is being tested with deep-sea divers. It is not available commercially.
Ketones give the iodoform test in which a free methyl group is linked to a carbonyl compound. In the above question, each option has a free methyl group linked to the carbonyl group but option B doesn’t so that would be the keto-ester.

Option (B) $C{{H}_{3}}COC{{H}_{2}}COO{{C}_{2}}{{H}_{5}}$ is the correct option.


Note:
Uses of iodoform are-
It is used as a disinfectant. It was also used as an antiseptic dressing and medicine for wounds at the beginning of the 20th century. It is also a component in-ear powders for cats and dogs. It also helps in the removal of ear hair.