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Chapter 2: 2.11 (page 68)

Estimate the pKaof 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 (Ka)quantifies the acid’s strength in a solution. The pKa 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 pKaof the nitrogen-hydrogen bond in H2N-His 38. Thus, the estimated pKa value of the nitrogen-hydrogen bond, that is, a primary amine,is also 38.


b. The pKa of the oxygen-hydrogen bond in CH3CH2O-His 16. Thus, the estimated pKavalue of the oxygen-hydrogen bond is also 16.

c. The pKa of the oxygen-hydrogen bond in HCOO-His 3.75. The addition of bromine tends to decrease the pKavalue to some extent. Thus, the estimated pKa 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 structure of a constitutional isomer of compound B that fits each description.

a. an isomer that is at least 105 times more acidic than B.

b. an isomer that is at least 105times less acidic than B.

c.an isomer that is comparable in acidity to B.

Many drugs are Brønsted-Lowry acids or bases.

a. What is the most acidic proton in the analgesic ibuprofen? Draw the conjugate base.

b. What is the most basic electron pair in cocaine? Draw the conjugate acid.

What is the conjugate base of each acid?

a. HCO3-

b.

c.

d.

Acetonitrile (CH3CN) has a pKaof 25, making it more acidic than many other compounds having only C-H bonds. Draw Lewis structures for acetonitrile and its conjugate base. Use resonance structures to account for the acidity of acetonitrile.

Label the acid and base and the conjugate acid and base in the following reactions. Use curved arrows to show the movement of electron pairs.

a.

b.
See all solutions

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