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Multiple Choice

A haloalkane is converted to an alcohol under reflux using which reagents?

The key idea is nucleophilic substitution of the halogen by a hydroxide source to form an alcohol. When haloalkanes are heated under reflux with a base such as NaOH (in water or an alcoholic medium), the hydroxide ion attacks the carbon attached to the halogen and replaces the halogen, giving an alkoxide that is then protonated to yield the alcohol. An alcohol solvent/base setup is used specifically because it supplies the OH− needed for substitution and provides the right medium for the reaction to proceed efficiently under heat. The other options don’t provide the hydroxide nucleophile needed for this substitution to alcohol, and they lead to different reactions (aldehydes engage in carbonyl chemistry, ethers form by reaction with alkoxide, carboxylic acids involve entirely different pathways). Hence, using an alcohol-containing reagent/medium is the appropriate choice to obtain the alcohol under reflux.

The key idea is nucleophilic substitution of the halogen by a hydroxide source to form an alcohol. When haloalkanes are heated under reflux with a base such as NaOH (in water or an alcoholic medium), the hydroxide ion attacks the carbon attached to the halogen and replaces the halogen, giving an alkoxide that is then protonated to yield the alcohol. An alcohol solvent/base setup is used specifically because it supplies the OH− needed for substitution and provides the right medium for the reaction to proceed efficiently under heat. The other options don’t provide the hydroxide nucleophile needed for this substitution to alcohol, and they lead to different reactions (aldehydes engage in carbonyl chemistry, ethers form by reaction with alkoxide, carboxylic acids involve entirely different pathways). Hence, using an alcohol-containing reagent/medium is the appropriate choice to obtain the alcohol under reflux.