Home
Class 11
CHEMISTRY
Propyne is less acidic than acetylene....

Propyne is less acidic than acetylene.

Text Solution

AI Generated Solution

The correct Answer is:
To understand why propyne is less acidic than acetylene, we can follow these steps: ### Step 1: Identify the Structures - **Acetylene (C₂H₂)** has the structure H-C≡C-H. - **Propyne (C₃H₄)** has the structure CH₃-C≡C-H. ### Step 2: Understand Acidity - Acidity in hydrocarbons is determined by the ability of the compound to donate a proton (H⁺). - The more stable the conjugate base formed after the donation of H⁺, the stronger the acid. ### Step 3: Form the Conjugate Bases - When acetylene donates a proton, it forms the acetylide ion (C₂H⁻): - H-C≡C-H → H⁺ + C≡C⁻ - When propyne donates a proton, it forms the propyne anion (C₃H⁻): - CH₃-C≡C-H → H⁺ + CH₃-C≡C⁻ ### Step 4: Analyze the Stability of Conjugate Bases - The conjugate base of acetylene (C≡C⁻) has no alkyl groups attached, making it less electron-dense and more stable. - The conjugate base of propyne (CH₃-C≡C⁻) has a methyl group (CH₃) attached, which exerts a +I (inductive) effect, increasing electron density around the negative charge. ### Step 5: Compare the Effects of Substituents - The +I effect from the methyl group in propyne destabilizes the conjugate base because it increases the electron density on the negatively charged carbon. - In contrast, the acetylide ion does not have such an electron-donating group, leading to a more stable conjugate base. ### Step 6: Conclusion - Since the conjugate base of propyne is less stable than that of acetylene, propyne is less acidic than acetylene. ### Summary - Acetylene is more acidic than propyne because its conjugate base is more stable due to the absence of electron-donating groups, while propyne's conjugate base is destabilized by the +I effect of the methyl group. ---
Promotional Banner

Topper's Solved these Questions

  • HYDROCARBONS

    MODERN PUBLICATION|Exercise Revision Exercises (Fill in the blanks Questions)|10 Videos
  • HYDROCARBONS

    MODERN PUBLICATION|Exercise Revision Exercises (Assertion Reason Questions)|10 Videos
  • HYDROCARBONS

    MODERN PUBLICATION|Exercise Revision Exercises (Passage Based Questions)|12 Videos
  • HALOALKANES AND HALOARENES

    MODERN PUBLICATION|Exercise UNIT PRACTICE TEST|12 Videos
  • HYDROGEN

    MODERN PUBLICATION|Exercise UNIT PRACTICE TEST (for Board Examination)|9 Videos

Similar Questions

Explore conceptually related problems

Phenol is less acidic than

Phenol is less acidic than