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Ph-overset(O)overset(||)C-NH2overset(POC...

`Ph-overset(O)overset(||)C-NH_2overset(POCl_3)rarr(A),` Product (A) is

A

`Ph-NH_2`

B

`Ph-CH_2-NH_2`

C

`Ph-overset(OH)overset(|)(CH)-NH_2`

D

`Ph-C-=N`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem, we need to determine the product (A) formed when the compound `Ph-C(=O)-NH2` reacts with `POCl3`. Here’s a step-by-step breakdown of the reaction: ### Step 1: Identify the Reactant The reactant is `Ph-C(=O)-NH2`, which consists of a phenyl group (Ph), a carbonyl group (C=O), and an amine group (NH2). ### Step 2: Understand the Role of POCl3 Phosphoryl chloride (POCl3) is a reagent that can facilitate the conversion of amides to nitriles. In this case, it will help in the dehydration of the amide to form a nitrile. ### Step 3: Resonance Stabilization The lone pair of electrons on the nitrogen atom (NH2) can participate in resonance with the carbonyl group. This resonance will stabilize the molecule and prepare it for the next step. ### Step 4: Formation of the Intermediate Upon treatment with POCl3, the nitrogen's lone pair can attack the carbonyl carbon, leading to the formation of an intermediate. This intermediate will have a positive charge on the nitrogen due to the donation of its lone pair. ### Step 5: Elimination of Chloride Ion The resonance structure allows for the elimination of a chloride ion (Cl-) from the intermediate. This occurs as the carbonyl group transforms into a good leaving group. ### Step 6: Formation of the Nitrile After the chloride ion leaves, the nitrogen atom will lose a hydrogen atom (H) and form a triple bond with the carbon atom. This results in the formation of a nitrile. ### Step 7: Final Product The final product (A) is `Ph-C≡N`, which is a phenyl nitrile. The by-products of the reaction include HCl and PO. ### Conclusion The product (A) formed from the reaction of `Ph-C(=O)-NH2` with `POCl3` is `Ph-C≡N`. ### Summary of Steps: 1. Identify the reactant. 2. Understand the role of POCl3. 3. Consider resonance stabilization. 4. Form an intermediate. 5. Eliminate chloride ion. 6. Form the nitrile. 7. Conclude with the final product.
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