JEE Mains · Chemistry · STD 12 -8.1. Aldehydes and ketones

An organic compound "\(x\)" where molar ratio of C, O and H are equal, on treatment with \(50\%\) KOH under reflux followed by acidification produced "\(y\)". The most likely structure of "\(y\)" is:
[Molar mass of '\(x\)' is \(58\) g mol\(^{-1}\)]

A \(CH_2 = CH - \overset{O}{\underset{\|}{C}} - OH\)
B \(CH_3 - CH = CH - CH = O\)
C \(O = C - OH, \, CH_2 - OH\) (with C-C bond)
D \(CH_3 - \overset{O}{\underset{\|}{C}} - OH\)

Verified Solution

Answer & Solution

Correct Answer

(C) \(O = C - OH, \, CH_2 - OH\) (with C-C bond)

Step-by-step Solution

Detailed explanation

Given the molar ratio of C, O, and H in compound \(x\) is equal, the empirical formula is \(CHO\). Empirical mass \(= 12 + 1 + 16 = 29\) g mol\(^{-1}\). Since the molar mass of \(x\) is \(58\) g mol\(^{-1}\), the molecular formula is \((CHO)_2\) or \(C_2H_2O_2\). The structure…

Apply the relevant identity from the chapter and substitute the values established in the previous step, keeping the original constraint in view.

Use the simplified expression to isolate the unknown, then plug the result back into the question setup to confirm the working is internally consistent.

Cross-check against a boundary or limiting case. Both the dimensional balance and the qualitative behaviour at the extreme should agree with the candidate answer.

Combine the steps above to identify the correct option. The remaining choices each fail at least one of the consistency, dimensional, or boundary checks.

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An organic compound "\(x\)" where molar ratio of C, O and H are equal, on treatment with \(50\%\) KOH under reflux followed by acidification produced "\(y\)". The most likely structure of "\(y\)" is:[Molar mass of '\(x\)' is \(58\) g mol\(^{-1}\)]

Step-by-step Solution

An organic compound "\(x\)" where molar ratio of C, O and H are equal, on treatment with \(50\%\) KOH under reflux followed by acidification produced "\(y\)". The most likely structure of "\(y\)" is:
[Molar mass of '\(x\)' is \(58\) g mol\(^{-1}\)]