back to directory
NEET CHEMISTRYAlcohols, Phenols and EthersMedium

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 Alcohols, Phenols and Ethers. 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.

CHEMISTRYAlcohols, Phenols and Ethersreactionsequencetextchtextchtextclxrightarrowtextnacnxrightarrowtexthtextni

More Alcohols, Phenols and Ethers Questions

View all

This neet chemistry practice question is part of the TopperSquare free question bank. TopperSquare offers 15,000+ chapter-wise NEET MCQs across Physics, Chemistry, and Biology with detailed step-by-step explanations, full mock tests, NEET PYQs (2010–2024), and an AI-powered performance analytics dashboard. browse all neet practice questions → · practice chemistry sets →