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underset((A))(EtCOCl) overset((i)H2 N.OH...

`underset((A))(EtCOCl) overset((i)H_2 N.OH) underset ((ii) overset(Ө)O H) rarr (B) overset(EtOH) rarr (C)`
Which of the following statements are correct about the given reaction ?

A

The compouds `(B)` and `( C)`, respectively, are `Et-C -= N` and `EtNH_2`.

B

The compounds `(B)` and `( C)`, respectively, are `EtN=C=O` and `EtNHCOOEt`.

C

The reaction is known as Lossen rearrangement reaction.

D

The reaction proceeds via the formation of acyl carbene `(EtCO ddot CH)` as the intermediate species.

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The correct Answer is:
To analyze the given reaction step by step, we will break down the transformations occurring from compound A to compound C. ### Step 1: Reaction of Compound A with Hydroxylamine - **Reaction**: The acid chloride (EtCOCl) reacts with hydroxylamine (H2N.OH). - **Mechanism**: - The nitrogen of hydroxylamine attacks the carbonyl carbon of the acid chloride. - This results in the formation of an intermediate where the chlorine (Cl) leaves as HCl. - The product of this step is an oxime (EtC=NOH). **Hint**: Identify the nucleophilic attack of hydroxylamine on the carbonyl carbon of the acid chloride. ### Step 2: Reaction in Basic Medium - **Reaction**: The oxime (EtC=NOH) is treated with a base (OH-). - **Mechanism**: - The hydroxide ion (OH-) abstracts a proton (H+) from the nitrogen of the oxime. - This results in the formation of a negatively charged intermediate (EtC=N-O^-). - A water molecule is eliminated in this process. **Hint**: Consider the role of the base in deprotonating the nitrogen atom. ### Step 3: Rearrangement (Lawson's Rearrangement) - **Reaction**: The negatively charged nitrogen attacks the carbonyl carbon. - **Mechanism**: - This step is known as Lawson's rearrangement. - The nitrogen donates its electrons to form a double bond with the carbon, resulting in the formation of compound B (EtC=N-O^-). **Hint**: Recognize the significance of the nitrogen's electron donation in the rearrangement process. ### Step 4: Reaction of Compound B with Ethanol - **Reaction**: Compound B (EtC=N-O^-) reacts with ethanol (EtOH). - **Mechanism**: - The nitrogen in compound B can be protonated by ethanol, or the ethyl group from ethanol can attack the carbon, leading to the formation of compound C. - The final product will have a carbonyl group (C=O) and an ethoxy group (OEt) attached to it, along with the nitrogen still bonded to one ethyl group and one hydrogen. **Hint**: Focus on how the ethyl group from ethanol can participate in the reaction to form the final product. ### Summary of Products - **Compound A**: Ethyl acyl chloride (EtCOCl) - **Compound B**: Ethyl oxime (EtC=N-OH) - **Compound C**: Ethyl carbamate or ethyl ester (C=O with OEt and NH with one ethyl) ### Conclusion After analyzing the steps, we can conclude which statements about the reaction are correct based on the transformations and mechanisms involved. The correct statements are: - Option B is correct (the reaction involves Lawson's rearrangement). - Option C is correct (the reaction does not proceed via carbene). ### Final Answer The correct statements about the given reaction are Option B and Option C. ---

To analyze the given reaction step by step, we will break down the transformations occurring from compound A to compound C. ### Step 1: Reaction of Compound A with Hydroxylamine - **Reaction**: The acid chloride (EtCOCl) reacts with hydroxylamine (H2N.OH). - **Mechanism**: - The nitrogen of hydroxylamine attacks the carbonyl carbon of the acid chloride. - This results in the formation of an intermediate where the chlorine (Cl) leaves as HCl. - The product of this step is an oxime (EtC=NOH). ...
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