JEE Main · 2025 · Shift-IImediumALCO-003

What is the correct IUPAC name of the following compound?

Alcohols, Phenols & Ethers · Class 12 · JEE Main Previous Year Question

Question

What is the correct IUPAC name of the following compound? image

Options
  1. a

    4-Ethyl-1-hydroxycyclopent-2-ene

  2. b

    1-Ethyl-3-hydroxycyclopent-2-ene

  3. c

    1-Ethylcyclopent-2-en-3-ol

  4. d

    4-Ethylcyclopent-2-en-1-ol

Correct Answerd

4-Ethylcyclopent-2-en-1-ol

Detailed Solution

Step 1: Identify the parent chain and principal characteristic group

The molecule is a cyclopentene (5-membered ring with one double bond) with an \ceOH\ce{-OH} group and an ethyl (\ceC2H5\ce{-C2H5}) substituent. The \ceOH\ce{-OH} 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 \ceOH\ce{-OH} 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 (\ceOH\ce{-OH}) 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 \ceOH\ce{-OH} 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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