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Reaction I Ph - overset(overset(O)(||))C...

Reaction I `Ph - overset(overset(O)(||))C - NH_2 overset( overset(oplus)(O) D, Br_2 ) (to) A`
Reaction II `Ph -overset(overset(O)(||)) C - ND_2 overset(overset(oplus)(O) D, Br_2) (to) B`
Products A and B are :

A

`Ph - NH_2 and Ph - ND_2`

B

`Ph - ND_2 and Ph - NH_2`

C

Both `Ph - NH_2`

D

Both `Ph - ND_2`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem, we need to analyze the two reactions step by step and determine the products formed in each case. ### Step 1: Identify the Reactants - **Reaction I**: The reactant is `Ph - C(=O) - NH2` (where Ph represents a phenyl group). - **Reaction II**: The reactant is `Ph - C(=O) - ND2`. ### Step 2: Understand the Reaction Conditions Both reactions are treated with `O D-` (deuterated hydroxide) and `Br2`. The presence of `O D-` suggests that deuterium will be involved in the reactions, affecting the products. ### Step 3: Mechanism of Reaction I 1. **Deprotonation**: The `O D-` abstracts a hydrogen atom from the amine group (`NH2`), forming `Ph - C(=O) - NH-`. 2. **Bromination**: The bromine (`Br2`) reacts with the nitrogen, resulting in `Ph - C(=O) - NBr`. 3. **Further Deprotonation**: Another `O D-` abstracts the remaining hydrogen, leading to a negatively charged nitrogen (`Ph - C(=O) - N-`). 4. **Elimination**: The nitrogen can lose a bromine atom, forming a nitrene intermediate. 5. **Migration**: The phenyl group migrates to the nitrogen, forming an isocyanate intermediate. 6. **Final Product Formation**: The reaction with `O D-` leads to the formation of `Ph - NH - C(=O) - O D` and eventually to `Ph - NH2` after tautomerization and decarboxylation. ### Step 4: Mechanism of Reaction II 1. **Deprotonation**: The `O D-` abstracts a deuterium from the amine group (`ND2`), forming `Ph - C(=O) - N D-`. 2. **Bromination**: The bromine (`Br2`) reacts with the nitrogen, resulting in `Ph - C(=O) - N DBr`. 3. **Further Deprotonation**: Another `O D-` abstracts the remaining deuterium, leading to a negatively charged nitrogen (`Ph - C(=O) - N-`). 4. **Elimination**: Similar to Reaction I, the nitrogen can lose a bromine atom, forming a nitrene intermediate. 5. **Migration**: The phenyl group migrates to the nitrogen, forming an isocyanate intermediate. 6. **Final Product Formation**: The reaction with `D2O` leads to the formation of `Ph - N D - C(=O) - O D` and eventually to `Ph - N D2` after tautomerization and decarboxylation. ### Step 5: Identify Products A and B - **Product A** from Reaction I: `Ph - NH2` - **Product B** from Reaction II: `Ph - N D2` ### Conclusion The products of the reactions are: - A = `Ph - NH2` - B = `Ph - N D2` Thus, the correct answer is option A: `Ph - NH2` and `Ph - N D2`. ---

To solve the problem, we need to analyze the two reactions step by step and determine the products formed in each case. ### Step 1: Identify the Reactants - **Reaction I**: The reactant is `Ph - C(=O) - NH2` (where Ph represents a phenyl group). - **Reaction II**: The reactant is `Ph - C(=O) - ND2`. ### Step 2: Understand the Reaction Conditions Both reactions are treated with `O D-` (deuterated hydroxide) and `Br2`. The presence of `O D-` suggests that deuterium will be involved in the reactions, affecting the products. ...
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