How many structural isomers can you draw for pentane?
Hint. Vary how branched the 5-carbon skeleton is — unbranched, one branch, or two branches.
Step 1 — Start with the unbranched chain. n-pentane: CH₃-CH₂-CH₂-CH₂-CH₃, a straight 5-carbon chain.
Step 2 — Introduce one branch. 2-methylbutane (isopentane): a 4-carbon chain with one -CH₃ branch on the second carbon.
Step 3 — Introduce two branches on the shortest possible chain. 2,2-dimethylpropane (neopentane): a 3-carbon chain with two -CH₃ branches both on the central carbon, since that's the only way to place two branches and still have 5 carbons total.
✦ Answer: 3 structural isomers — n-pentane, 2-methylbutane, and 2,2-dimethylpropane.
Where students slip. Missing 2,2-dimethylpropane because both branches sit on the same carbon — it's easy to assume branches must go on different carbons, but placing both methyl groups on the central carbon of propane gives a genuinely distinct, valid isomer.
