Rank the following alcohols from strongest to weakest acid.
CH2═CHCH2OH; CH3CH2CH2OH; HC≡CCH2OH
Bruice 8th Edition
Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry
Problem 63
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Rank the following alcohols from strongest to weakest acid.
CH2═CHCH2OH; CH3CH2CH2OH; HC≡CCH2OH
Explain the relative acidities.
CH2═CHCH2OH, CH3CH2CH2OH, HC≡CCH2OH
b. Determine the exact pKa values, using a calculator.
c. Which is the strongest acid?
1. nitrous acid (HNO2), Ka = 4.0 × 10−4
2. nitric acid (HNO3), Ka = 22
3. bicarbonate (HCO3−), Ka = 6.3 × 10−11
4. hydrogen cyanide (HCN), Ka = 7.9 × 10−10
5. formic acid (HCOOH), Ka = 2.0 × 10−4
6. phosphoric acid (H3PO4), Ka = 2.1
Give the products of the following acid–base reactions and indicate whether reactants or products are favored at equilibrium.
b. CH3CH2OH + -NH2 ⇌
Given the Ka values, estimate the pKa value of each of the following acids without using a calculator (that is, is it between 3 and 4, between 9 and 10, and so on?):
1. nitrous acid (HNO2), Ka = 4.0 × 10−4
2. nitric acid (HNO3), Ka = 22
3. bicarbonate (HCO3−), Ka = 6.3 × 10−11
4. hydrogen cyanide (HCN), Ka = 7.9 × 10−10
5. formic acid (HCOOH), Ka = 2.0 × 10−4
6. phosphoric acid (H3PO4), Ka = 2.1
For each compound, indicate the atom that is most apt to be protonated.
a.
b.
c.