Asked in ETEA MDCAT 2010 2010Moderate

Displacement reaction that proceeds by the SN2 mechanism are most successful with compounds that are:

Correct answer: D. Primary compound with no branch at β- carbon

  • A. Neopentyl system
  • B. Tertiary compound with no branch
  • C. Secondary halides
  • D. Primary compound with no branch at β- carbon

Explanation

Primary compounds with no branching at the β-carbon, are generally the most suitable for SN2 reactions. They have the least steric hindrance, facilitating the attack of the nucleophile from the backside of the carbon and resulting in efficient substitution. Therefore, the most successful compounds for displacement reactions via the SN2 mechanism are primary compounds with no branching at the β-carbon.

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About Nucleophilic Substitution

Nucleophilic substitution replaces a leaving group in an alkyl halide when an electron-rich nucleophile attacks the carbon atom. The topic compares SN1 and SN2 mechanisms, including reaction conditions, substrate structure, solvent effects, nucleophile strength, carbocation formation and stereochemical changes, and distinguishes substitution from elimination.

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