Asked in UHS MDCAT 2012 2012Moderate

The alkaline hydrolysis of bromoethane shown below gives alcohol as the product H3C―CH2―Br → H3C―CH2―OH. The reagent and the condition used in this reaction may be:

Correct answer: D. Dilute NaOH(aq) warm

  • A. H2O at room temperature
  • B. Ethanol, heat
  • C. KOH in alcohol
  • D. Dilute NaOH(aq) warm

Explanation

The given reaction is an example of alkaline hydrolysis or nucleophilic substitution reaction in which a halogen atom in an alkyl halide is replaced by a hydroxyl (-OH) group from a nucleophilic hydroxide ion (OH-).The reaction conditions required for this reaction are basic and involve the use of a strong nucleophile, which is provided by the hydroxide ion. Dilute NaOH(aq) is commonly used as a reagent for this reaction, as it provides the necessary conditions for hydrolysis to occur. The reaction is usually carried out under reflux conditions (heating with constant boiling) to drive the reaction to completion.

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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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