Question

which will have higher boiling point -1-chloropentane or 2-methyl-2-chlorobutane

Answer 1

2-chlorobutane has a higher boiling point than 2-methyl-1-chloropropane.
These are isomers and 2-methyl-1-chloropropane has a more branched structure.
Branched isomers have a lower boiling point than their straight chain isomer.

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