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NEET CHEMISTRYHaloalkanes and HaloarenesMedium

Question

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.

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Haloalkanes and Haloarenes. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.

CHEMISTRYHaloalkanes and Haloarenesreactionsequencetextchtextchtextclxrightarrowtextnacnxrightarrowtexthtextni

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