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Organic Chemistry | 7th Edition | ISBN: 9781269406772 | Authors: Paula Yurkanis Bruice
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Ethyne has a pKa value of 25, water has a pKa value of

Chapter 2, Problem 16P

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QUESTION:

Problem 16P

Ethyne has a pKa value of 25, water has a pKa value of 15.7, and ammonia (NH3) has a pKa value of 36. Draw the equation, showing equilibrium arrows that indicate whether reactants or products are favored, for the acid–base reaction of ethyne with

a. HO-. b. –NH2.

c. Which would be a better base to use if you wanted to remove a proton from ethyne, HO- or -NH2 ?

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QUESTION:

Problem 16P

Ethyne has a pKa value of 25, water has a pKa value of 15.7, and ammonia (NH3) has a pKa value of 36. Draw the equation, showing equilibrium arrows that indicate whether reactants or products are favored, for the acid–base reaction of ethyne with

a. HO-. b. –NH2.

c. Which would be a better base to use if you wanted to remove a proton from ethyne, HO- or -NH2 ?

ANSWER:

Solution 16P :

Step 1 of 4:

Here, we are asked to draw the equation for the acid–base reaction of ethyne with the given compounds, showing equilibrium arrows indicating whether reactants or products are favored.

        To determine if the equilibrium favours reactants or products in an acid-base reaction, we take help of pka value. We compare the pKa value of the acid on the reactants side(on the left of the equilibrium arrows) with the pKa value of the acid on the products side(on the right of the equilibrium arrows). The Equilibrium always favours the weaker acid which has higher pKa value.

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