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Q. 2.48

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Organic Chemistry
Found in: Page 86

Short Answer

Which compounds can be deprotonated by , so that equilibrium favors the products? Refer to the pKa table in Appendix A.

a. HCOOH

b.

c.

d.

The compounds a and b are stronger acids and can be deprotonated by . However, compounds c and d are weaker acids and cannot be deprotonated by .

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Step by Step Solution

Deprotonation

The removal of a ion from the Brønsted-Lowry acid in an acid-base reaction is called the deprotonation of the acid.

Acid dissociation constant

The acid dissociation constant is the strength estimation of an acid. In the Brønsted-Lowry concept, the stronger the acid, the more is its speed of donating a proton.

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

To choose a base to deprotonate the given acid

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 a higher than the given acid.

Comparison of the given compounds

The conjugate acid of is with a value of 15.7. The given compounds can be deprotonated by only if their value is lower than that of .

  1. The value of HCOOH is 3.8. Hence, HCOOH is a stronger acid than and is deprotonated by .
  2. The value of is 7.0 which is lower than that of the value of . Hence is deprotonated by .
  3. The value of the given compound is 41 which is higher than that of the value of . Hence this compound cannot be deprotonated by .
  4. The value of is 40 which is higher than that of the value of . Hence cannot be deprotonated by .

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