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underset((A)) (EtCOOMe) overset("(i)" NH...

`underset((A)) (EtCOOMe) overset("(i)" NH_2 NH_2 "(ii)" HNO_2) underset("(iii)" overset (Ө) OH "(iv)" H_3 O^(oplus))rarr(B)`
The product `(B)` is :

A

`MeNH_2`

B

`EtNH_2`

C

`MeCONH_2`

D

`EtCONHMe`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the given problem, we will go through the reactions step by step. ### Step 1: Identify the starting compound (A) The starting compound is Ethyl Methyl Carboxylate (EtCOOMe), which can be represented as: - Ethyl group (Et) = C2H5 - Methyl group (Me) = CH3 Thus, the structure can be written as: \[ \text{EtCOOMe} \equiv \text{C}_2\text{H}_5\text{COOCH}_3 \] ### Step 2: Reaction with Hydrazine (NH2NH2) When Ethyl Methyl Carboxylate reacts with hydrazine (NH2NH2), it undergoes a nucleophilic substitution where the hydrazine replaces the methoxy group (OMe): \[ \text{EtCOOMe} + \text{NH}_2\text{NH}_2 \rightarrow \text{EtCOONHNH}_2 \] This gives us Ethyl Hydrazone: \[ \text{EtCOONHNH}_2 \] ### Step 3: Reaction with Nitrous Acid (HNO2) The next step involves the reaction with nitrous acid (HNO2), which converts the hydrazine group (NH2) to a hydroxyl group (OH): \[ \text{EtCOONHNH}_2 + \text{HNO}_2 \rightarrow \text{EtCOONH}_2\text{OH} \] This results in the formation of an intermediate compound with a hydroxyl group: \[ \text{EtCOONH}_2\text{OH} \] ### Step 4: Reaction with Hydroxide Ion (OH-) The intermediate compound then reacts with hydroxide ion (OH-), leading to the loss of a water molecule: \[ \text{EtCOONH}_2\text{OH} + \text{OH}^- \rightarrow \text{EtCOONH} \] This results in the formation of a compound with an amine group: \[ \text{EtCOONH} \] ### Step 5: Rearrangement (Lossen Rearrangement) The next step involves a rearrangement known as Lossen rearrangement, where the ethyl group migrates to the nitrogen: \[ \text{EtCOONH} \rightarrow \text{EtNCO} \] This gives us an isocyanate: \[ \text{EtNCO} \] ### Step 6: Reaction with Hydronium Ion (H3O+) Finally, when the isocyanate reacts with hydronium ion (H3O+), it hydrolyzes to form an amine: \[ \text{EtNCO} + \text{H}_3\text{O}^+ \rightarrow \text{EtNH}_2 + \text{CO}_2 \] This results in the formation of Ethylamine (EtNH2) and carbon dioxide (CO2). ### Final Product (B) The final product (B) is: \[ \text{EtNH}_2 \] ### Summary of Steps: 1. **Identify starting compound (A)**: Ethyl Methyl Carboxylate (EtCOOMe). 2. **React with hydrazine (NH2NH2)**: Forms Ethyl Hydrazone (EtCOONHNH2). 3. **React with nitrous acid (HNO2)**: Converts NH2 to OH, forming (EtCOONH2OH). 4. **React with hydroxide ion (OH-)**: Leads to loss of water, forming (EtCOONH). 5. **Undergo Lossen rearrangement**: Ethyl group migrates to nitrogen, forming (EtNCO). 6. **React with hydronium ion (H3O+)**: Hydrolyzes to form Ethylamine (EtNH2) and CO2.

To solve the given problem, we will go through the reactions step by step. ### Step 1: Identify the starting compound (A) The starting compound is Ethyl Methyl Carboxylate (EtCOOMe), which can be represented as: - Ethyl group (Et) = C2H5 - Methyl group (Me) = CH3 Thus, the structure can be written as: \[ \text{EtCOOMe} \equiv \text{C}_2\text{H}_5\text{COOCH}_3 \] ...
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