Chemistry · Isomerism

NEET (UG) 2025 — Question 79

Total number of possible isomers (both structural and stereoisomers) of cyclic ethers of molecular formula CX4HX8O\ce{C4H8O} is:

  1. Option A:

    6

  2. Option B:

    8

  3. Option C:

    10

    Correct
  4. Option D:

    11

Answer: C

Step-by-step solution

For CX4HX8O\ce{C4H8O}, degree of unsaturation is (2×4+2−8)/2=1(2\times4 + 2 - 8)/2 = 1, so every isomer contains one ring. Possible ring sizes: oxirane (3-membered, CX2HX4O\ce{C2H4O}) plus two extra carbons; oxetane (4-membered, CX3HX6O\ce{C3H6O}) plus one extra carbon; and tetrahydrofuran (5-membered, CX4HX8O\ce{C4H8O}). Constitutional isomers from oxirane: 2-ethyloxirane\ce{2-ethyloxirane}, 2,2-dimethyloxirane\ce{2,2-dimethyloxirane}, and 2,3-dimethyloxirane\ce{2,3-dimethyloxirane}. From oxetane: 2-methyloxetane\ce{2-methyloxetane} and 3-methyloxetane\ce{3-methyloxetane}; from the 5-membered ring: tetrahydrofuran\ce{tetrahydrofuran}. Stereoisomer counts: 2-ethyloxirane = 2 enantiomers; 2,2-dimethyloxirane = 1; 2,3-dimethyloxirane = 3 (one cis/meso form and one trans-enantiomeric pair); 2-methyloxetane = 2 enantiomers; 3-methyloxetane = 1; tetrahydrofuran = 1. Total = 2+1+3+2+1+1=102+1+3+2+1+1 = 10. Hence the correct option is C (10).

Solution figure

Answer key and solution verified before publishing.

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Exam
NEET (UG) 2025
Subject
Chemistry
Chapter
Isomerism
Topic
Introduction & Structural Isomerism
Total number of possible isomers (both structural and stereoisomers)… | NEET (UG) 2025 PYQ with Solution · DhiX AI