Explain the acidic nature of ethyne.

Vedclass pdf generator app on play store
Vedclass iOS app on app store
(N/A) The $s$-orbital is closer to the nucleus and more electronegative than the $p$-orbital. Therefore,the electronegativity of carbon increases as the percentage of $s$-character increases.
The order of electronegativity is: $sp \text{ } C > sp^{2} \text{ } C > sp^{3} \text{ } C$.
Due to this,the $sp$-hybridized carbon in ethyne $(HC \equiv CH)$ attracts the shared pair of electrons of the $C-H$ bond towards itself more strongly than $sp^{2}$ or $sp^{3}$ hybridized carbons.
This makes the hydrogen atom attached to the $sp$-hybridized carbon acidic in nature.
$50\% \text{ } s$-character in $sp$ carbon makes the $C-H$ bond polar,allowing the $H$ to be released as a proton $(H^{+})$ in the presence of strong bases.
Chemical reactions showing the acidic nature of ethyne:
$1$. Reaction with sodium metal:
$HC \equiv CH + Na \xrightarrow{475 \ K} HC \equiv C^{-}Na^{+} + \frac{1}{2} H_{2}$
$2$. Reaction with sodamide $(NaNH_{2})$:
$HC \equiv CH + NaNH_{2} \xrightarrow{liq. NH_{3}} HC \equiv CNa + NH_{3}$
$HC \equiv CH + 2NaNH_{2} \xrightarrow{liq. NH_{3}} Na^{+}C^{-} \equiv C^{-}Na^{+} + 2NH_{3}$
Thus,terminal alkynes exhibit weak acidic character.

Explore More

Similar Questions

What is the product when acetylene reacts with hypochlorous acid $(HOCl)$?

Which of the following is used to distinguish ethylene and acetylene?

Propene and propyne can be distinguished by

The final product of the following reaction is .......
$CaO + 3C$ $\xrightarrow{\text{Heat}} A$ $\xrightarrow{H_2O} B$ $\xrightarrow{H_2SO_4, Hg^{2+}} C$

The number of $\pi$-bonds in the product formed by passing acetylene through dilute sulphuric acid containing mercuric sulphate is

Difficult
View Solution

Vedclass Products

For Students

Vedclass Test Series

Mock tests in real JEE/NEET style with performance analysis. 5-day free trial.

Start Free Trial
For Teachers

Exam Paper Generator

Generate Set A/B/C/D exam papers from 7.5L+ questions in 2 minutes. 3 chapters free.

Try Free
For Institutes

Online Exam Module

Live online exams with unlimited students, 360° analytics & white-label branding.

See Demo