Which of the conjugate bases of the following acids will be strong enough to deprotonate acetylene.

World of Chemistry, 3rd edition
3rd Edition
ISBN:9781133109655
Author:Steven S. Zumdahl, Susan L. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan L. Zumdahl, Donald J. DeCoste
Chapter16: Acids And Bases
Section: Chapter Questions
Problem 5A
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Which of the conjugate bases of the following acids will be strong enough to deprotonate acetylene.  Indicate the letter of all that apply:

a. C4H10

b. NH3

c. CH3CH2OH

d. CH3CO2H

e. H

f. HCl

Expert Solution
Step 1

The PKa value of actylene is 25 . 

Therefore to deprotonate acetylene , the acid should have value greater than PKa = 25

a) C4H10   CH3CH2CH2CH2-  .It has a PKof 48

b) NH3  NH2 . It has a PKof 38 

c) CH3CH2OH  CH3CH2O-  . It has a PKof approx. 4 -5.

d) CH3CO2CH3CO2 . It has a PKof approx 16-19.

e) H  No conjugate 

f) HCl Cl- . It has a PKof -7

 

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