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Q. 2.47

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Organic Chemistry
Found in: Page 86

Short Answer

Which of the following bases are strong enough to deprotonate ( = 25), so that equilibrium favors the products:

Bases (c), (e), and (f) are strong to deprotonate .

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Step by Step Solution

Deprotonation

Removal of the most acidic ion from a Bronsted-Lowry acid in an acid-base reaction is known as deprotonation.

Acid dissociation constant

The acid dissociation constant is represented as or is a measure of the strength of an acid. In the Brønsted-Lowry concept, the stronger acid is the one that donates a proton i.e., ion quickly.

An acid with a higher or lower is a strong acid.

Choosing a base to deprotonate the given acid  

The acid which gets deprotonated first is stronger acid and hence, has a lower . Hence, an acid must have a higher to deprotonate another acid.

So, a base can deprotonate an acid if the conjugate acid of the base has higher than the given acid.

Comparison of the given bases

For , ; hence in order to deprotonate this acid, the conjugate acid of the given base should have a higher .

(a) The conjugate acid of is with the value of -1.7. Since the of is lower than the of , so, cannot deprotonate the given acid.

(b) The conjugate acid of NaOH is with the value of 15.7. Since the of is lower than the of , so, NaOH cannot deprotonate the given acid.

(c) The conjugate acid of is with the value of 38. Since the of is higher than the of , NaOH is strong enough as a base to deprotonate the given acid.

(d) The conjugate acid of is with the value of 9.4. Since the of is lower than the of , so, cannot deprotonate the given acid.

(e) The conjugate acid of NaH is with the value of 35. Since the of is higher than the of , NaH is strong enough as a base to deprotonate the given acid.

(f) The conjugate acid of is with the value of 50. Since the of is higher than the of , is strong enough as a base to deprotonate the given acid.

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