What is the correct IUPAC name of the following compound?
Alcohols, Phenols & Ethers · Class 12 · JEE Main Previous Year Question
What is the correct IUPAC name of the following compound?
- a
4-Ethyl-1-hydroxycyclopent-2-ene
- b
1-Ethyl-3-hydroxycyclopent-2-ene
- c
1-Ethylcyclopent-2-en-3-ol
- d✓
4-Ethylcyclopent-2-en-1-ol
4-Ethylcyclopent-2-en-1-ol
Step 1: Identify the parent chain and principal characteristic group
The molecule is a cyclopentene (5-membered ring with one double bond) with an group and an ethyl () substituent. The group is the principal characteristic group, so the suffix is -ol. The parent name is cyclopent-2-en-1-ol (the ring).
Step 2: Number the ring to give the -OH the lowest locant
In IUPAC 2013 rules for cyclic alcohols:
- The carbon bearing gets locant 1 (since -ol suffix takes priority).
- The double bond runs C2–C3 (giving the lowest locant to the double bond).
- The ethyl group is at C4.
Step 3: Common wrong approaches
Students often number to give the double bond locant 1, which is incorrect — the principal characteristic group () always gets the lowest possible locant before the double bond in IUPAC nomenclature.
Another mistake is using "hydroxy" as a prefix (option a style) — when is the principal group, it must appear as the suffix "-ol", not as "hydroxy-".
Step 4: Verify
- Parent: cyclopentane → cyclopentene (double bond) → cyclopent-2-en-1-ol (OH at C1, double bond at C2)
- Substituent: ethyl at C4
- Full name: 4-Ethylcyclopent-2-en-1-ol ✓
Key Points to Remember:
- In IUPAC nomenclature, the principal characteristic group (-OH for alcohols) gets the lowest locant.
- The suffix "-ol" is used, not "hydroxy-" as prefix, when -OH is the principal group.
- Numbering direction is chosen to give lowest locant set to substituents after fixing the principal group position.
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