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Chapter 2: 2.11 (page 68)

Estimate the ${pK}_{a}$ of each of the indicated bonds.
a.
b.
c.

Short Answer

Expert verified

a. 38

b. 16

c.2.9

Step by step solution

01

Dissociation constant of acid

The dissociation constant of acid $(K_{a})$ quantifies the acid’s strength in a solution. The ${pK}_{a}$ value is less if the acid is strong and vice-versa.

02

Relation between the conjugate base and acidic strength

The acid’s strength is inversely correlated to the strength of its conjugate base. If the acid is weak then the conjugate base will be strong.

03

Estimation of pKa of bonds

a. The ${pK}_{a}$ of the nitrogen-hydrogen bond in $H_{2} N - H$ is 38. Thus, the estimated ${pK}_{a}$ value of the nitrogen-hydrogen bond, that is, a primary amine,is also 38.

b. The ${pK}_{a}$ of the oxygen-hydrogen bond in ${CH}_{3} {CH}_{2} O - H$ is 16. Thus, the estimated ${pK}_{a}$ value of the oxygen-hydrogen bond is also 16.

c. The ${pK}_{a}$ of the oxygen-hydrogen bond in $HCOO - H$ is 3.75. The addition of bromine tends to decrease the ${pK}_{a}$ value to some extent. Thus, the estimated ${pK}_{a}$ value of the oxygen-hydrogen bond in bromoacetic acid is also 2.9.

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Most popular questions from this chapter

Draw the products formed from the acid-base reaction of HCl with each compound.

a.

b.

c.

d.

For each pair of compounds: [1] Which indicated H is more acidic? [2] Draw the conjugate base of each acid. [3] Which conjugate base is stronger?

a.

b.

What is the $K_{a}$ for each compound?

a.

b.

c.

Question: Use a calculator when necessary to answer the following questions.

a. What is the ${pK}_{a}$ for each $K_{a}$ : $10^{- 10}$ , $10^{- 21}$ and $5.2 \times 10^{- 5}$ ?

b. What is the for each $K_{a}$ : 7, 11, and 3.2?

Dimethyl ether ${(CH}_{3} {OCH}_{3})$ and ethanol ${(CH}_{3} {CH}_{2} OH)$ are isomers, but ${CH}_{3} {OCH}_{3}$ has a role="math" localid="1649252571433" $pKa$ of 40 and ${CH}_{3} {CH}_{2} OH$ has a $pKa$ of 16. Why are these $pKa$ values so different?

See all solutions

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