Haloalkanes and Haloarenes

Question

Arrange each set of compounds in order of increasing boiling points:








Answer

Both of the alkyl halides are primary. However, the substituent CH3 is at a greater distance to the carbon atom linked to Br in 1- bromo-3-methylbutane than in 1-bromo-2-methylbutane. Therefore, the approaching nucleophile is less hindered in case of the 1-bromo-3-methylbutane than in case of the 1-bromo-2-methylbutane. Hence, 1-bromo-3-methylbutane reacts faster than the latter by SN2 mechanism.


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