Acids & Bases/
Organic Chemistry
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Acids and Bases in Organic Chemistry: A Comprehensive Guide with Exercises, Slides of Organic Chemistry
A comprehensive overview of acids and bases in organic chemistry, covering key concepts such as arrhenius and brønsted-lowry definitions, acid-base equilibrium, conjugate acid-base pairs, weak acids, organic acids and bases, pka and pkb values, and lewis acids and bases. It includes numerous examples, exercises, and questions to reinforce understanding and promote critical thinking.
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2023/2024
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Acids & Bases/
Organic Chemistry
Models of Acids and Bases
- Arrhenius: Acids produce H+^ & bases
produce OH
ion in aqueous solutions.
- Brønsted-Lowry: Acids are H+^ donors &
bases are proton acceptors.
- HCl + H 2
O Cl
+ H
3
O
acid base
QUESTION: 1
Aniline, C 6
H
5
NH
2 , was isolated in the 1800s and began immediate use in the dye industry. What is the formula of the conjugate acid of this base? A. C 6
H
5
NH
2
B. C 6
H
5
NH
3
C. C 6
H
5
NH
D. C 6
H
5
NH
E. C 6
H
5
NH
2
Weak Acids
- (^) Weak acids are only partially ionized in solution. or
- (^) K a is the acid dissociation constant.
Conjugates
Ka x Kb =? What do pK a and pK b refer to? pKa + pKb =? Remember: pH + pOH = pKw
Which is the stronger acid? Which is the stronger base?
QUESTION: 2
Use information on the table above to determine which of the following bases would have the weakest conjugate acid: OC 6 H 5
- ; C 2 H 3 O 2 - ; OCl - ; NH 3 A. OC 6 H 5
B. C 2 H 3 O 2
C. OCl
D. NH 3
Acid and Base Equilibria The equilibrium favors the weaker of the acid vs. its conjugate acid or base vs. its conjugate. Weak wins! http://chemconnections.org/organic/Movies%20Org%20Flash/acid-base-eq.swf
QUESTION: 3.
Consider the following equilibria. Identify the weaker of the two: acid vs. its conjugate acid in each reaction. Which reactions favor formation of product?
A. All do: 1- B. 1, 4, 5 C. 2, 3, 6 D. 1, 5 E. None do. Worksheet 5: Acids & Bases http://chemconnections.org/organic/chem226/226assign-12.html#Worksheets
Formal Charge / Acids & Bases
Electrophiles / Nucleophiles / Reactivity Worksheet 1 http://chemconnections.org/organic/chem226/226assign-12.html#Worksheets
Structure and Acid-Base Properties
Important factors that effect acidity in binary compounds, eg HCl (having only two elements):
- (^) Bond Length ( shorter = stronger bonds; lower acidity)
- (^) Bond Strength ( longer = weaker bonds; higher acidity: more dissociation, more protons [hydronium ions] in solution)
- (^) Bond Polarity ( smaller e.n. differences favor higher acidities)
HBr is a stronger acid than HF. The greater the e.n. difference, the more polar the bond, the shorter and stronger the bond, and since it is harder to dissociate (break), the weaker the acid.
Strength of Oxyacids
(Three atoms: ternary vs. binary)
Induction or a ”Push-Pull” electronic effect influences the proton, which weakens the oxygen-hydrogen bond. Chlorine (higher e.n.) pulls electrons more than Iodine (lower e.n.)