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Example · Example 2

Q.Draw and name all the chain (structural) isomers of C5H12\text{C}_5\text{H}_{12}, and state how their boiling points compare.

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✓ Free question

C5H12\text{C}_5\text{H}_{12} can be arranged in three distinct ways: a straight chain, CH3CH2CH2CH2CH3\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_3 (n-pentane); a singly-branched chain, (CH3)2CHCH2CH3(\text{CH}_3)_2\text{CHCH}_2\text{CH}_3 (2-methylbutane, or isopentane); and a doubly-branched, highly compact chain, (CH3)4C(\text{CH}_3)_4\text{C} (2,2-dimethylpropane, or neopentane). Boiling point is set by the strength of London dispersion forces between molecules, which depend on how much surface area is available for intermolecular contact -- a long, thin, straight-chain molecule has more surface contact than a compact, near-spherical branched one, so boiling point falls steadily as branching increases: n-pentane (36 °C36\,°\text{C}) >> isopentane (28 °C28\,°\text{C}) >> neopentane (9.5 °C9.5\,°\text{C}).

✓Final answer

Three isomers exist: n-pentane >> isopentane >> neopentane, in decreasing boiling point, as branching increases.

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