Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Amines

Question:

Match List I with List II

List I List II
I. Hoffmann Bromamide degradation reaction
B. \(CH_3NH_2\) II. Azo dye formation
C. \(CH_3CH_2CONH_2\) III. Gabriel phthalimide synthesis
IV. Carbylamine reaction

Choose the correct answers from the options given below:

Options:

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

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

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

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

Correct Answer:

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

Explanation:

The correct answer is Option (2) → A-II, B-IV, C-I, D-III

List I List II
 II. Azo dye formation 
B. \(CH_3NH_2\) IV. Carbylamine reaction
C. \(CH_3CH_2CONH_2\) I. Hoffmann Bromamide degradation reaction
III. Gabriel phthalimide synthesis

II. Azo dye formation :

The formation of aniline azo dyes involves a two-step process: diazotization followed by coupling.

Diazotization: Aniline \((C_6H_5NH_2)\) is converted into a diazonium salt. This step typically requires the following:

Aniline: The starting material.

Nitrous acid (HNO_2): Formed in situ by mixing sodium nitrite \((NaNO_2)\) with an acid like hydrochloric acid \((HCl)\).

Temperature: The reaction is carried out at low temperatures, typically 0–5°C, to stabilize the diazonium salt.

This forms the benzenediazonium chloride \((C_6H_5N_2^+Cl^-)\).

Coupling Reaction

In the next step, the diazonium salt reacts with a phenol or aniline derivative to form the azo dye. The reaction is highly dependent on pH and is typically carried out in mildly alkaline conditions.

Coupling component: A phenol (e.g., phenol itself or substituted phenols) or aniline is used.

Azo coupling: The diazonium ion couples with the electron-rich aromatic ring of phenol or aniline, typically at the para or ortho position relative to the hydroxyl or amino group.

This forms p-hydroxyazobenzene, an example of an azo dye. The characteristic N=N (azo) bond gives the compound its color.

IV. Carbylamine reaction:

The carbylamine reaction (also called the isocyanide test) is a chemical reaction used to detect primary amines. In this reaction, a primary amine reacts with chloroform (CHCl₃) and a strong base like potassium hydroxide (KOH) to form an isocyanide (or carbylamine), which has a very unpleasant odor.

Mechanism:

I. Hoffmann Bromamide degradation reaction:

The correct reaction to convert acetamide (\(CH_3CONH_2\)) to methylamine (\(CH_3NH_2\)) is the Hoffmann Bromamide reaction.

In this reaction, acetamide is treated with bromine and alkali (like NaOH or KOH). The reaction results in the removal of the carbonyl group from the amide, converting it into a primary amine (in this case, methylamine). This is a very efficient method for converting amides to amines with one fewer carbon atom.

Mechanism:

III. Gabriel phthalimide synthesis: 

Gabriel synthesis, also known as Gabriel phthalimide synthesis, is a method used for preparing primary amines. Here is a step-by-step outline of the process:

Formation of N-alkylphthalimide: 

Phthalimide (\( C_6H_4(CO)_2NH \)) is first reacted with an alkyl halide (such as an alkyl bromide) in the presence of a base (e.g., potassium hydroxide) to form N-alkylphthalimide. The general reaction is:

Hydrolysis of N-alkylphthalimide:

The N-alkylphthalimide intermediate is then hydrolyzed with a strong base (e.g., sodium hydroxide) or an acid to yield the primary amine and phthalic acid. The hydrolysis reaction is: