MolSynapsequestion bank
MolSynapse / Question bank / General Organic Chemistry I: Electronic Effects / Resonance structures of drawn ions and radicals
JEE Advanced levelSingle correct optionDifficulty 3 of 3g1231

A strong base removes a proton from the sp3 carbon of the compound shown. How many resonance structures (all with complete octets, differing only in the position of the charge and pi bonds) can be written for the anion formed?

  1. A2
  2. B3
  3. C4
  4. D5

Answer: D

The compound shown is cyclopenta-1,3-diene. Removing a proton from CH2 gives the cyclopentadienyl anion. The negative charge can be placed on each of the five carbons, and each placement is a distinct structure. So there are 5.
Practice General Organic Chemistry I: Electronic Effects More on Resonance structures of drawn ions and radicals

More questions on Resonance structures of drawn ions and radicals