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NEET CHEMISTRYAlcohols, Phenols and EthersMedium

Question

In SN2S_N2 substitution reaction of the type R-Br+ClDMFR-Cl+Br\text{R-Br} + \text{Cl}^- \xrightarrow{\text{DMF}} \text{R-Cl} + \text{Br}^-, which one of the following has the highest relative rate?

A

CH3-CH2-CH2Br\text{CH}_3\text{-CH}_2\text{-CH}_2\text{Br}

B

CH3-CH(CH3)-CH2Br\text{CH}_3\text{-CH(CH}_3\text{)-CH}_2\text{Br}

C

CH3-C(CH3)2-CH2Br\text{CH}_3\text{-C(CH}_3)_2\text{-CH}_2\text{Br}

D

CH3CH2Br\text{CH}_3\text{CH}_2\text{Br}

Step-by-Step Solution

The given reaction proceeds via an SN2S_N2 mechanism. The rate of an SN2S_N2 reaction is highly dependent on the steric hindrance (spatial arrangement) around the electrophilic carbon atom. As the steric bulk around the α\alpha-carbon increases, the approach of the incoming nucleophile (Cl\text{Cl}^-) is hindered, leading to a lower reaction rate. Among the given primary alkyl bromides, bromoethane (CH3CH2Br\text{CH}_3\text{CH}_2\text{Br}) has the least steric hindrance. Branching at the β\beta-carbon (as seen in the other options: propyl, isobutyl, and neopentyl bromides) increases steric resistance, making the approach of the nucleophile difficult. Thus, CH3CH2Br\text{CH}_3\text{CH}_2\text{Br} has the highest relative rate.

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 Etherssubstitutionreactiontextrbrtextclxrightarrowtextdmf

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