Match List I with List II.

Choose the correct answer from the options given below:

A-III, B-I, C-IV, D-II

The correct answer is Option (1) → A-III, B-I, C-IV, D-II.

Let us break down each component in the matching task to clarify their roles and relationships in organic chemistry, particularly focusing on amines and their reactions.

A. Hoffman Bromamide Reaction

The Hofmann bromamide reaction is a method used to convert primary amides into primary amines. It involves treating a primary amide with bromine (or N-bromosuccinimide) in the presence of a strong base (like sodium hydroxide).

The product is an amine with one fewer carbon atom than the starting amide.

This reaction produces an amine with lesser number of carbon atoms.

B. Carbylamine Reaction

The carbylamine reaction (or isocyanide test) is a well-known qualitative test for the presence of primary amines. When a primary amine is treated with chloroform and a strong base (like potassium hydroxide), an isocyanide (carbylamine) is formed, which has a very strong and unpleasant odor.

This reaction serves as a detection test for primary amines, making it match with I: Detection Test for primary amines.

C. Gabriel Phthalimide Synthesis

The Gabriel synthesis is a method for preparing primary amines from phthalimide. In this reaction, phthalimide is treated with a strong base (like potassium hydroxide) and an alkyl halide (R-X) to form an N-alkylphthalimide intermediate, which is then hydrolyzed to yield a primary amine.

This process clearly aligns with IV: Reaction of phthalimide with KOH and R-X.

D. Benzene Sulphonyl Chloride (Hinsberg Reagent)

Benzene sulfonyl chloride is used in the Hinsberg test to differentiate between primary, secondary, and tertiary amines.

The Hinsberg test is a classical method used to distinguish between primary, secondary, and tertiary amines based on their different chemical behaviors with Hinsberg's reagent (benzenesulfonyl chloride, \( C_6H_5SO_2Cl \)).

Reactions with Hinsberg's Reagent:

Primary Amine:

A primary amine \((R-NH_2)\) reacts with Hinsberg's reagent to form a sulphonamide derivative:

The sulphonamide formed still contains a hydrogen atom attached to the nitrogen. This hydrogen is slightly acidic. When treated with an alkali like NaOH, this sulphonamide dissolves because the acidic hydrogen reacts with the base, forming a soluble salt:

The solution becomes clear due to the solubility of the resulting salt in the alkali.

Secondary Amine:

A secondary amine \((R_2NH)\) reacts with Hinsberg's reagent to form a sulphonamide as well:

However, this sulphonamide lacks the acidic hydrogen that could make it soluble in alkali. When treated with NaOH, this sulphonamide does not dissolve because it cannot form a soluble salt. The solution remains cloudy or forms a precipitate.

Tertiary Amine:

A tertiary amine \((R_3N)\) does not react with Hinsberg's reagent at all, because it lacks any hydrogen attached to the nitrogen:

There is no product to dissolve or react with NaOH.  No change; no clear solution forms.

Conclusion

In conclusion, each of these reactions has specific applications in organic chemistry, especially regarding the identification and synthesis of amines. The Hofmann bromamide reaction is primarily a synthesis reaction, while the carbylamine reaction is a classic qualitative test for primary amines. The Gabriel synthesis is a method for producing primary amines from phthalimide, and benzene sulfonyl chloride serves as a useful reagent for differentiating among types of amines. If any specific part of this analysis needs further clarification, feel free to ask!