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Question 67

Consider the following organic reaction sequence. Choose the final product (X) from the following (consider the major product in all intermediate reactions)

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  1. Step (i): Amide Formation $$(\text{NH}_3 / \Delta)$$
    Propanoic acid $$(\text{CH}_3\text{CH}_2\text{COOH})$$ reacts with ammonia and heat to undergo a dehydration reaction, converting the carboxylic acid group into an amide:
    $$\text{CH}_{3}\text{CH}_{2}\text{COOH}\xrightarrow{\text{NH}_{3},\ \Delta }\text{CH}_{3}\text{CH}_{2}\text{CONH}_{2}\quad \text{(Propanamide)}$$
  2. Step (ii): Hoffmann Bromamide Degradation $$(\text{NaOH} / \text{Br}_2)$$
    Propanamide reacts with bromine in the presence of sodium hydroxide. This causes degradation by losing the carbonyl $$(\text{C}=\text{O})$$ group, yielding a primary amine with one less carbon atom:
    $$\text{CH}_{3}\text{CH}_{2}\text{CONH}_{2}\xrightarrow{\text{NaOH}/\text{Br}_{2}}\text{CH}_{3}\text{CH}_{2}\text{NH}_{2}\quad \text{(Ethanamine)}$$
  3. Step (iii): Diazotization and Hydrolysis $$(\text{HNO}_2 / \text{H}_2\text{O}, 0^\circ\text{C})$$
    Ethanamine reacts with nitrous acid $$(\text{HNO}_{2})$$ at a low temperature to form an unstable aliphatic diazonium salt, which instantly undergoes nucleophilic substitution with water $$(\text{H}_2\text{O})$$ to form ethanol:
    $$\text{CH}_{3}\text{CH}_{2}\text{NH}_{2}\xrightarrow{\text{HNO}_{2}/\text{H}_{2}\text{O},\ 0^{\circ }\text{C}}\text{CH}_{3}\text{CH}_{2}\text{OH}\quad \text{(Ethanol)}$$
  4. Step (iv): Reduction of Benzenediazonium Chloride $$(\text{C}_6\text{H}_5\text{N}_2\text{Cl}, 0^\circ\text{C})$$
    When ethanol is mixed with benzenediazonium chloride $$(\text{C}_6\text{H}_5\text{N}_2\text{Cl})$$, it acts as a reducing agent. Ethanol reduces the diazonium salt to Benzene while itself getting oxidized to ethanal (acetaldehyde):
    $$\text{C}_{6}\text{H}_{5}\text{N}_{2}\text{Cl}+\text{CH}_{3}\text{CH}_{2}\text{OH}\xrightarrow{0^{\circ }\text{C}}\text{C}_{\mathbf{6}}\text{H}_{\mathbf{6}}\mathbf{\ (Benzene)}+\text{N}_{2}+\text{CH}_{3}\text{CHO}+\text{HCl}$$

Correct Option
Benzene

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