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A overset(Ph-SO(2)Cl)rarrB overset("KOH"...

`A overset(Ph-SO_(2)Cl)rarrB overset("KOH")rarrCoverset(C_(2)H_(5)I)rarrD`
'C' is water soluble
Correct structure of A and D are

A

`R-NH_(2)" ,"Ph-SO_(2)-NR-(C_(2)H_(5))_(2)^(+)I^(-)`

B

`R-NR-R" ,"Ph-SO_(2)-NR_(2)-C_(2)H_(5)`

C

`R-NH_(2)" ,"Ph-SO_(2)-NR-I`

D

`R_(2)NH" ,"Ph-SO_(2)-NR_(2)-(C_(2)H_(5))^(+)I^(-)`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem step by step, we will analyze the reactions and identify the structures of compounds A and D based on the information provided. ### Step 1: Identify Compound A - **Given Reaction**: A reacts with Benzene Sulfonyl Chloride (Ph-SO₂Cl). - **Understanding the Reaction**: Benzene Sulfonyl Chloride is known as Hinsberg reagent, which is used to distinguish between primary, secondary, and tertiary amines. - **Conclusion**: Since Compound C is water-soluble after the reaction with KOH, Compound A must be a primary amine (R-NH₂). ### Step 2: Write the Structure of Compound A - **Structure of A**: The general structure of a primary amine is R-NH₂, where R can be any alkyl or aryl group. Thus, we can represent Compound A as: \[ \text{A: } R-NH_2 \] ### Step 3: Analyze the Reaction to Form Compound B - **Reaction with Hinsberg Reagent**: The primary amine (R-NH₂) reacts with Ph-SO₂Cl. The nitrogen atom attacks the sulfur atom, leading to the formation of a sulfonamide. - **Structure of B**: The resulting compound (B) will have the structure: \[ \text{B: } R-NH^+(SO_2Ph) + Cl^- \] ### Step 4: Reaction of Compound B with KOH to Form Compound C - **Reaction with KOH**: When compound B is treated with KOH, the hydroxide ion (OH⁻) will deprotonate the nitrogen, resulting in a water-soluble salt. - **Structure of C**: The resulting compound (C) will have the structure: \[ \text{C: } R-N^-(SO_2Ph) + K^+ \] ### Step 5: Identify Compound D - **Reaction of C with Ethyl Iodide (C₂H₅I)**: Compound C reacts with ethyl iodide to form compound D. The nucleophilic nitrogen will attack the ethyl iodide, leading to the formation of a quaternary ammonium salt. - **Structure of D**: The resulting compound (D) will have the structure: \[ \text{D: } R-N^+(C_2H_5)_2(SO_2Ph) + I^- \] ### Final Structures - **Structure of A**: \( R-NH_2 \) (Primary amine) - **Structure of D**: \( R-N^+(C_2H_5)_2(SO_2Ph) + I^- \) (Quaternary ammonium salt)
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