Give a brief note on the acidic nature of alkynes.

Vedclass pdf generator app on play store
Vedclass iOS app on app store
(N/A) The $s$-orbital is closer to the nucleus than the $p$-orbital,so electronegativity increases as the $s$-character increases. The order of electronegativity is: $sp > sp^2 > sp^3$.
Due to this,the $sp$ hybridized carbon in an alkyne attracts the bonded electron pair most strongly towards itself. Consequently,the hydrogen atom attached directly to the $sp$ carbon is more acidic than the hydrogen atoms in alkanes or alkenes.
Acidic strength order: $\equiv C-H > =C-H > -C-H$.
Only the hydrogen atom attached to the triply bonded carbon of a terminal alkyne (like $HC \equiv CH$,$CH_3 C \equiv CH$,$CH_3 CH_2 C \equiv CH$) is acidic. In $R-C \equiv C-H$,only the terminal $H$ is acidic. In $R-C \equiv C-R$,there is no acidic hydrogen.
Chemical reactions showing the acidic nature of terminal alkynes:
Ethyne reacts with strong bases like sodium metal at high temperatures or sodamide $(NaNH_2)$ to form ethynide (acetylide) products.
$1$. Reaction with sodium metal:
$HC \equiv CH + Na \xrightarrow{475 \ K} HC \equiv C^- Na^+ + \frac{1}{2} H_2$ (Eq. $i$)
$2$. Reaction with sodamide:
$HC \equiv CH + NaNH_2 \xrightarrow{NH_3} HC \equiv CNa + NH_3$ (Eq. $ii$)
$HC \equiv CH + 2NaNH_2 \xrightarrow{NH_3} Na^+C^- \equiv C^-Na^+ + 2NH_3$ (Eq. $iii$)

Explore More

Similar Questions

$[P]$ $\xrightarrow{Br_{2}} C_{2}H_{4}Br_{2}$ $\xrightarrow{NaNH_{2}/NH_{3}} [Q]$
$[Q]$ $\xrightarrow{20 \% H_{2}SO_{4}, Hg^{2+}, \Delta} [R]$ $\xrightarrow{Zn-Hg/HCl} [S]$
The species $[P], [Q], [R]$ and $[S]$ respectively are:

Which one of the following is more acidic?

What will be $X$ in the following reaction?
${C_2}{H_2} \xrightarrow[{HgSO_4 / H_2SO_4, 60^{\circ}C}]{{H_2O}} X \rightleftharpoons CH_3CHO$

Difficult
View Solution

Predict the product $C$ obtained in the following reaction of but$-1-$yne: $CH_3-CH_2-C \equiv CH + HCl \to B \xrightarrow{HCl} C$

Difficult
View Solution

Which of the following is used for the conversion of $2$-hexyne into $trans$-$2$-hexene?

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