Which will undergo deprotonation most readily in basic medium?
General Organic Chemistry (GOC) · Class 11 · JEE Main Previous Year Question
Which will undergo deprotonation most readily in basic medium?
- a✓
A only
- b
C only
- c
Both A and C
- d
B only
A only
Step 1: Acidity of Active Methylene Protons
Deprotonation occurs most readily where the conjugate base is most stable.
- Structure A: 2,4-pentanedione. The active methylene hydrogens are flanked by two methyl ketones. The and effects of two keto groups stabilize the anion.
- Structure B: Dimethyl malonate. Esters are less electron-withdrawing than ketones due to the effect of the alkoxy group.
- Structure C: Ethyl acetoacetate. One ketone and one ester.
Step 2: Conclusion Structure A has two ketone groups, which provide the strongest stabilization to the conjugate base compared to esters.
Practice this question with progress tracking
Want timed practice with adaptive difficulty? Solve this question (and hundreds more from General Organic Chemistry (GOC)) inside The Crucible, our adaptive practice platform.
More JEE Main General Organic Chemistry (GOC) PYQs
The least acidic compound, among the following is:
The order of relative stability of the contributing structure is:
What will be the decreasing order of basic strength of the following conjugate bases? OH⁻, RO⁻, CH₃COO⁻, Cl⁻
Correct sequence of acidic strength of the following aliphatic acids in their decreasing order is: CH₃CH₂COOH, CH₃COOH, CH₃CH₂CH₂COOH, HCOOH
A species with carbon having sextet of electrons, acting as electrophile: