MCQMediumJEE 2026Amines (Classification & Properties)

JEE Chemistry 2026 Question with Solution

A student performed analysis of aliphatic organic compound 'X' which on analysis gave C = 61.01%61.01\%, H = 15.25%15.25\%, N = 23.74%23.74\%. This compound, on treatment with HNO2/H2OHNO_2/H_2O produced another compound 'Y' which did not contain any nitrogen atom. However, the compound 'Y' upon controlled oxidation produced another compound 'Z' that responded to iodoform test. The structure of 'X' is:

  • A

    Ph—CH—NH2_2 \quad (with CH3_3 substituent)

  • B

    CH3_3—CH—NH2_2 \quad (with CH3_3 substituent)

  • C

    CH3_3—CH2_2—CH—CH3_3 \quad (with NH2_2 substituent)

  • D

    CH3_3—CH2_2—CH2_2—NH2_2

Answer

Correct answer:B

Step-by-step solution

Standard Method

Given: The compound X is an aliphatic organic compound with composition C = 61.01%61.01\%, H = 15.25%15.25\%, N = 23.74%23.74\%.

Find: The structure of X.

Step 1: Empirical formula check The given percentages match isopropylamine, that is CH3CH(NH2)CH3CH_3-CH(NH_2)-CH_3.

Step 2: Reaction with HNO2/H2OHNO_2 / H_2O Primary aliphatic amines react with nitrous acid to give alcohols.

CH3CH(NH2)CH3CH3CH(OH)CH3CH_3-CH(NH_2)-CH_3 \rightarrow CH_3-CH(OH)-CH_3

So compound Y is isopropanol, which contains no nitrogen atom.

Step 3: Controlled oxidation of Y Isopropanol on oxidation gives acetone.

CH3CH(OH)CH3CH3COCH3CH_3-CH(OH)-CH_3 \rightarrow CH_3-CO-CH_3

So compound Z is acetone.

Step 4: Iodoform test Acetone gives a positive iodoform test because it contains the COCH3COCH_3 group.

Therefore, X = isopropylamine, and the correct option is B.

Reaction Pathway Logic

Given: X forms a nitrogen-free compound Y with HNO2/H2OHNO_2/H_2O, and Y on controlled oxidation gives Z which responds to iodoform test.

Find: Which option matches X.

From the nitrous acid reaction:

  • Primary aliphatic amines give alcohols.
  • Secondary amines give nitroso compounds.
  • Tertiary amines do not give this conversion.

Hence X must be a primary aliphatic amine.

Now Y gives, on oxidation, a compound positive to iodoform test. This means Y must be a secondary alcohol of the type that oxidizes to a methyl ketone.

CH3CH(OH)CH3[O]CH3COCH3CH_3-CH(OH)-CH_3 \xrightarrow{[O]} CH_3-CO-CH_3

Thus Y is isopropanol.

So the starting amine X must be the corresponding amine:

CH3CH(NH2)CH3CH_3-CH(NH_2)-CH_3

This is isopropylamine.

Therefore, the correct option is B.

Common mistakes

  • Assuming any amine will form an alcohol with HNO2/H2OHNO_2/H_2O is incorrect. Only primary aliphatic amines undergo this conversion; secondary and tertiary amines behave differently. First identify the class of amine before predicting the product.

  • Using only the percentage composition and ignoring the reaction sequence is wrong. Several formulas may appear plausible, but the correct structure must also explain formation of a nitrogen-free alcohol and then a compound giving iodoform test.

  • Forgetting that a positive iodoform test indicates a methyl ketone or a corresponding secondary alcohol is a conceptual error. Here oxidation product Z must be acetone, so Y must be isopropanol.

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