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NEET CHEMISTRYMedium

Given below is a reaction sequence: CH3CH2ClNaCNXH2/NiYAcetic AnhydrideZ\text{CH}_3\text{CH}_2\text{Cl} \xrightarrow{\text{NaCN}} X \xrightarrow{\text{H}_2/\text{Ni}} Y \xrightarrow{\text{Acetic Anhydride}} Z

The product 'ZZ' in the above reaction is:

A

CH3CH2CH2NHCOCH3\text{CH}_3\text{CH}_2\text{CH}_2\text{NHCOCH}_3

B

CH3CH2CH2NH2\text{CH}_3\text{CH}_2\text{CH}_2\text{NH}_2

C

CH3CH2CH2CONHCH3\text{CH}_3\text{CH}_2\text{CH}_2\text{CONHCH}_3

D

CH3CH2CH2CONHCOCH3\text{CH}_3\text{CH}_2\text{CH}_2\text{CONHCOCH}_3

Step-by-Step Solution

The given reaction sequence involves the following three steps:

  1. Nucleophilic substitution: Ethyl chloride (CH3CH2Cl\text{CH}_3\text{CH}_2\text{Cl}) reacts with sodium cyanide (NaCN\text{NaCN}) undergoing a substitution reaction. Because cyanide is an ambident nucleophile and NaCN\text{NaCN} is predominantly ionic, the attack takes place mainly through the carbon atom, resulting in the formation of propanenitrile (XX) . CH3CH2Cl+NaCNCH3CH2CN (X)+NaCl\text{CH}_3\text{CH}_2\text{Cl} + \text{NaCN} \rightarrow \text{CH}_3\text{CH}_2\text{CN} \text{ (X)} + \text{NaCl}

  2. Reduction: Propanenitrile (XX) undergoes catalytic hydrogenation in the presence of H2/Ni\text{H}_2/\text{Ni} to form a primary amine, propan-1-amine (YY). CH3CH2CN+2H2NiCH3CH2CH2NH2 (Y)\text{CH}_3\text{CH}_2\text{CN} + 2\text{H}_2 \xrightarrow{\text{Ni}} \text{CH}_3\text{CH}_2\text{CH}_2\text{NH}_2 \text{ (Y)}

  3. Acylation: The primary amine, propan-1-amine (YY), undergoes acylation upon treatment with acetic anhydride to form an N-substituted amide, N-propylacetamide (ZZ). CH3CH2CH2NH2+(CH3CO)2OCH3CH2CH2NHCOCH3 (Z)+CH3COOH\text{CH}_3\text{CH}_2\text{CH}_2\text{NH}_2 + (\text{CH}_3\text{CO})_2\text{O} \rightarrow \text{CH}_3\text{CH}_2\text{CH}_2\text{NHCOCH}_3 \text{ (Z)} + \text{CH}_3\text{COOH}

Thus, the final product 'ZZ' is CH3CH2CH2NHCOCH3\text{CH}_3\text{CH}_2\text{CH}_2\text{NHCOCH}_3.

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