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R-NH-COH underset("pyridine")overset(POC...

`R-NH-COH underset("pyridine")overset(POCl_(3))(to)` product. In the given reaction what will be the product.

A

`R-N=C=O`

B

`N-overset(+)(N)-=C^(-)`

C

`R-C-=N`

D

None of these

Text Solution

AI Generated Solution

The correct Answer is:
To solve the question regarding the reaction of R-NH-COH with POCl3 in the presence of pyridine, we will follow these steps: ### Step 1: Identify the Reactants We have the reactant R-NH-COH (which is an amide) and we are reacting it with POCl3 (phosphoryl chloride) in the presence of pyridine. **Hint:** Identify the functional groups present in the reactant and the role of the reagents. ### Step 2: Understand the Role of POCl3 POCl3 is a dehydrating agent. It can facilitate the conversion of amides to isocyanates by removing water (dehydration). **Hint:** Recall how dehydrating agents typically function in organic reactions. ### Step 3: Mechanism of Reaction 1. The nitrogen atom in the amide (R-NH-COH) has a lone pair that can attack the phosphorus atom in POCl3. This forms a positively charged intermediate. 2. The chlorine atom in POCl3 acts as a good leaving group and will leave, resulting in a positively charged nitrogen and a double bond between carbon and oxygen. **Hint:** Consider the electron movement and the formation of intermediates during the reaction. ### Step 4: Formation of Isocyanate After the formation of the intermediate, a proton (H+) is removed, leading to the formation of an isocyanate (R-N=C=O) as the final product. The nitrogen will carry a positive charge, and the carbon will be triple-bonded to nitrogen. **Hint:** Think about the stability of the resulting product and the nature of the bonds formed. ### Step 5: Identify the Product The product formed from this reaction is R-N=C=O, which is isocyanate. **Hint:** Compare the final product with the options provided in the question to confirm the correct answer. ### Conclusion The product of the reaction of R-NH-COH with POCl3 in the presence of pyridine is an isocyanate (R-N=C=O). ### Final Answer The correct product is R-N=C=O (isocyanate). ---
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