Which of the following bases are strong enough to deprotonate CH3CH2CH2C≡CH (pKa = 25) so that equilibrium favors the products: NaC ≡ N    NaH    CF3COONa    CH3Li    CH3ONa    NaNH2

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter18: Carboxylic Acids
Section: Chapter Questions
Problem 18.35P
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Which of the following bases are strong enough to deprotonate CH3CH2CH2C≡CH (pKa = 25) so that equilibrium favors the products:

NaC
N
  
NaH
  
CF3COONa
  
CH3Li
  
CH3ONa
  
NaNH2
Expert Solution
Step 1

Given:

  pKa value of (CH3CH2CH2C≡CH) is 25 .

To find the bases to deprotonates the alkyne.

 

Explanation:

The base contains pKa value higher than 25 will only can deprotonate the alkyne. Then only the equilibrium favours the product.

So, first to determine the conjugate acid of the given bases and its pKa value.

Pka value of conjugate acids is higher than 25 is needed to deprotonate the alkyne.

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