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Arrange the following compounds in increasing order of their boiling points: (I) C2H5OH (II) C2H5Cl (III) C2H5CH3 (i.e. propane) (IV) C2H5OCH3 (methoxyethane)

1. (III) < (II) < (I) < (IV)
2. (II) < (III) < (IV) < (I)
3. (IV) < (III) < (I) < (II)
4. (III) < (IV) < (II) < (I)

Correct answer: (III) < (IV) < (II) < (I)

Solution

Propane (only weak dispersion) is lowest, then methoxyethane (weak dipole, no H-bond), then chloroethane (larger dipole/heavier), and ethanol highest due to strong O-H hydrogen bonding.

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