Question:

Which will undergo deprotonation most readily in basic medium?
Which will undergo deprotonation most readily in basic medium?

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Resonance stabilization of the conjugate base increases the acidity of the compound, favoring deprotonation.

Updated On: Jan 8, 2025
  • Both a and c
  • a only
  • b only
  • c only
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The Correct Option is B

Approach Solution - 1

Deprotonation is most favored when the conjugate base formed is resonance-stabilized. In structure (a), deprotonation leads to the formation of a conjugate base stabilized by resonance between the keto group and the enolate ion. Structures (b) and (c) do not have such strong resonance stabilization.

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Approach Solution -2

Correct answer is (B) a only

Real Life Applications

The real-life applications of the deprotonation of acids in the basic medium are as follows: 

  • As pH indicators, they tend to change color based on the medium or the concentration of hydrogen ions. The medium with more protonation is more acidic.
  • It can be used during buffer solution. A buffer solution helps in stabilizing the pH of the medium. They either absorb or release the protons, depending on the pH of the solution.
  • In organic chemistry and during the study of biochemistry.
pH scale

Question can also be asked as

  1. Which compound is the most acidic in the basic medium?
  2. Name the compound with the lowest pKa in the basic medium.
  3. Which compound has the most stable conjugate base in a basic medium?
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Questions Asked in JEE Main exam

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Concepts Used:

Introduction to Organic Chemistry

Organic chemistry is the branch of chemistry that involves the scientific study of organic compounds. Organic chemistry primarily deals with the structure and chemical composition of organic compounds, the physical and chemical properties of organic compounds, and the chemical reactions undergone by these compounds.

Reaction Intermediates in Organic Chemistry:

Intermediates can be understood as the first product of a consecutive reaction. For example, in a chemical reaction, if A→B and B→C, then, B can be said to be the intermediate for reaction A→C. The reactions in organic chemistry occur via the formation of these intermediates.

Reagents in Organic Chemistry:

Reagents are the chemicals that we add to bring about a specific change to an organic molecule. Any general reaction in organic chemistry can be written as:

Substrate + Reagent → Product

Where the substrate is an organic molecule to which we add the reagent. Based on the ability to either donate or abstract electrons, the reagents can be classified as:

  • Electrophiles
  • Nucleophiles