Question #70429

1 Answer
Ernest Z. · Media Owl
May 16, 2015

Both ethyl chloride and allyl chloride react with aqueous sodium hydroxide at normal temperatures.

Ethyl chloride is a gas, and alkyl halides are relatively nonpolar.

You would have to do the reaction in a mixed solvent like aqueous acetone (acetone to dissolve the halide; water to dissolve the sodium hydroxide).

Ethyl chloride is a 1° halide, so it will react slowly by an #"S"_"N"2# mechanism.

Allyl chloride is an allylic halide. It reacts much faster than ethyl chloride (by an #"S"_"N"1# mechanism), because the intermediate carbocation is stabilized by resonance.

Resonance hybrid from www.chem.ucalgary.ca

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