MHT CET · Chemistry · Aldehydes and Ketones

A dihaloalkane ' \(X\), having formula \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{Cl}_{2}\), on hydrolysis gives a compound, that can reduce Tollen's reagent. The compound \(X^{\prime}\) is

A 1,2 -dichloropropane
B 1 , 1 -dichloropropane
C 1,3 -dichloropropane
D 2, 2-dichloropropane

Verified Solution

Answer & Solution

Correct Answer

(B) 1 , 1 -dichloropropane

Step-by-step Solution

Detailed explanation

Since, the obtained compound reduces Tollen's reagent, it must be an aldehyde. Thus, it is obvious that both the \(-\mathrm{Cl}\) atoms are present at \(\mathrm{C}_{1} . \quad\) Hence, \(\quad\) the \(\quad\) compound \(\quad{X}^{\prime}\) is 1, 1-dichloropropane and the reactions are as follows

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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