Which of these reagents can be used to separate ` 1^@ , 2 ^@ and 3 ^@ ` amines ?

Options

A. Benzene sulphonamide
B. ethyl malonate
C. Diethyl ozalate
D. Benzene sulphonic acid

Answer

To determine which reagent can be used to separate primary, secondary, and tertiary amines, we can analyze the provided options based on their chemical reactions with these amines.

### Step-by-Step Solution:

1. **Understanding the Types of Amines**:
- Primary amines (RNH2) have one alkyl group attached to the nitrogen.
- Secondary amines (R2NH) have two alkyl groups attached to the nitrogen.
- Tertiary amines (R3N) have three alkyl groups attached to the nitrogen.

2. **Analyzing the Reagents**:
- **Option A: Benzene Sulfonamide**:
- Benzene sulfonamide (Hinsberg reagent) reacts with amines to form sulfonamides. However, it does not differentiate between primary, secondary, and tertiary amines since all can form sulfonamides. Thus, it cannot be used for separation.

- **Option B: Ethyl Malonate**:
- Ethyl malonate does not react significantly with amines to form distinct products. The reaction with primary and secondary amines would yield similar products, making separation impossible. Thus, this option is also incorrect.

- **Option C: Diethyl Oxalate**:
- Diethyl oxalate reacts with primary amines to form solid oxamides, while it reacts with secondary amines to form liquid products (dialkyloxamic esters). Tertiary amines do not react at all due to the absence of a hydrogen atom on the nitrogen. Thus, this reagent can effectively separate the three types of amines based on the physical state of the products formed (solid vs. liquid).

- **Option D: Benzene Sulfonic Acid**:
- Benzene sulfonic acid will protonate all types of amines, leading to similar ionic products without differentiation. Therefore, it cannot be used for separation.

3. **Conclusion**:
- The correct reagent that can be used to separate primary, secondary, and tertiary amines is **Option C: Diethyl Oxalate**.