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Structural Isomerism

Mediumchemistry

A saturated acyclic compound has the molecular formula C_5H_12; how many distinct structural isomers can be drawn for this alkane?

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About This Question

Subject
chemistry
Chapter
some basic principles of organic chemistry
Topic
structural isomerism
Difficulty
Medium
Year
2025
Tags
structural isomerismchain isomerscarbon skeletonpentane isomersconnectivity

Solution

Correct Answer:

Structural isomers are compounds with the same molecular formula but different connectivity of atoms, and counting them requires systematically varying the carbon skeleton. For C_5H_12 the possible skeletons are the straight chain n-pentane, the singly branched 2-methylbutane (isopentane), and the doubly branched 2,2-dimethylpropane (neopentane). These three chain arrangements exhaust all unique connectivities, so there are exactly three structural isomers. The answer 2 is wrong because it omits the highly branched neopentane skeleton. The answer 4 overcounts by treating a renamed version of an existing skeleton as new, which violates the rule that identical connectivity is one isomer. The answer 5 grossly overcounts and cannot be realised with only five carbons. This classic isomer-counting exercise appears directly in NCERT for the pentanes and is a building block for later counting of positional and functional isomers in substituted compounds. A systematic method is to start from the longest chain, then progressively shorten it while adding branches in all non-equivalent positions, taking care never to recount a skeleton already drawn in a different orientation. The three pentane isomers also differ measurably in boiling point because branching reduces surface contact. Plausibility check: drawing each skeleton and confirming that no two share the same connectivity verifies that only three genuinely different structures exist for C_5H_12.

This medium difficulty chemistry question is from the chapter some basic principles of organic chemistry, covering the topic of structural isomerism. It appeared in the 2025 exam.

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