Identify the compound that will react with Hinsberg's reagent to give a solid which dissolves in alkali. 1. CH₃CH₂-ddotNO₂ 2. CH₃CH₂-ddotNH-CH₃ 3. CH₃CH₂-ddotNH₂ 4. (CH₃CH₂)₂ddotN-CH₃

Answer: 3. CH₃CH₂-ddotNH₂ Key idea: Hinsberg's reagent (benzenesulphonyl chloride) reacts with primary and secondary amines; the sulphonamide of a primary amine has an acidic N-H and dissolves in alkali. CH₃CH₂NH₂ is primary: its product C₆H₅SO₂NHC₂H₅ dissolves in alkali. The secondary amine gives an alkali-insoluble product; the tertiary amine does not react; nitroethane is not an amine.

Topic: Identification of 1/2/3 amines· Organic Compounds Containing Nitrogen

Identify the compound that will react with Hinsberg's reagent to give a solid which dissolves in alkali.

four structures: nitroethane, N-methylethanamine, ethanamine, N-ethyl-N-methylethanamine (as drawn)

1. \(CH_3CH_2-\ddot{N}O_2\)

2. \(CH_3CH_2-\ddot{N}H-CH_3\)

3. \(CH_3CH_2-\ddot{N}H_2\)

4. \((CH_3CH_2)_2\ddot{N}-CH_3\)

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Answer: 3. \(CH_3CH_2-\ddot{N}H_2\)

Key idea: Hinsberg's reagent (benzenesulphonyl chloride) reacts with primary and secondary amines; the sulphonamide of a primary amine has an acidic N-H and dissolves in alkali.

\(\mathrm{CH_3CH_2NH_2}\) is primary: its product \(\mathrm{C_6H_5SO_2NHC_2H_5}\) dissolves in alkali. The secondary amine gives an alkali-insoluble product; the tertiary amine does not react; nitroethane is not an amine.

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Identify the compound that will react with Hinsberg's reagent to give a solid which dissolves in alkali.

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