[Lecture Note]

유기 화학 I (CHE2102)
Chapter 2 : Acid and Base

[What we learn in this chapter]

- Type of acid & base : Bronsted-Lowry & Lewis
- Strength of acid & base
- Direction of the reaction between acid & base

2.1 Brønsted-Lowry Acids and Bases

- Proton = H+ (hydrogen atom without its electron is a proton)
- Brønsted-Lowry acid: proton donor
Brønsted-Lowry base: proton acceptor (having lone pair electrons or π-bond)
- Morphine and amino acid: have both hydrogen atoms (acid) and lone pairs (base)

2.2 Reactions of Brønsted-Lowry Acids and Bases

- transfer of a proton from an acid to a base

- Loss of a proton from an acid forms “conjugate base”

Gain of a proton by a base forms its “conjugate acid”
- In general, electron-rich species (base) react with electron-deficient species (acid).

2.3 Acid Strength and pKa

- The more readily a compound donates a proton (the more A withdraws electrons from H), the
stronger an acid it is.
- Acidity: measured by an equilibrium constant
- Acidity constant, Ka

- pKa value

- Where to use pKa in research: determine concentration of acid and conjugate base in certain pH

- Acidity of some common comounds

2.4 Predicting the Outcome of Acid-Base Reactions

- Check relative strengths of the acids and bases: equilibrium always favors formation of the weaker
acid and base (see Sample Problem 2.4)
 1. Identify the acid and base
2. Draw the products of proton transfer and identify the conjugate acid and base
3. Compare the pKa values of the acid and the conjugate acid

2.5 Factors that Determine Acid Strength

- Stabilizes a conjugate base A:¯ makes the starting acid H-A more acidic
- The more stable the conjugate base, the more acidic the acid
- 4 effects
1. Element effects
2. Inductive effects
3. Resonance effects
4. Hybridization effects
- Element effect
Electronegativity trends (row in the periodic table)

Size trends (column in the periodic table)***

- Inductive effect: pull of electron density through σ bonds
More electronegative atoms stabilize regions of high electron density by an electron withdrawing
inductive effect.
The more electronegative the atom and the closer it is to the site of the negative charge, the
greater the effect.

- Resonance effect: delocalization of charge through resonance stabilizes conjugate base

- Resonance effect > inductive effect

- Hybridization effect

- See “How to” in p. 77

- Example:

2.6 Common Acids and Bases

- Acids

- Bases
 Strong bases have weak conjugate acids with high pKa values, usually > 12
Carbanion: strong base

2.7 Aspirin

- Deprotonated ionic form (right): soluble in the aqueous blood stream

Protonated neutral form (left): pass through hydrophobic cell membranes

2.8 Lewis Acids and Bases

- Lewis acid: electron pair acceptor (group 3A)
Lewis base: electron pair donor (lone electron pair, π-bond)
- All Brønsted-Lowry acids are also Lewis acids, but the reverse is not necessarily true
All Brønsted-Lowry bases are also Lewis bases, and the revewrse is always true
- Lewis acid-base reaction: Lewis base donates an electron pair to a Lewis acid, forming new bond

- Lewis acid: electrophile

(When a Lewis base reacts with an electrophile other than a proton) Lewis base: nucleophile
- In the case of Lewis acid&base reaction making no additional bond:
1. Always identify the Lewis acid and base first.
2. Draw a curved arrow from the electron pair of the base to the electron-deficient atom of the
acid.
 3. Count electron pairs and break a bond when needed to keep the correct number of valence
electrons

Problem solving: 2.39, 42, 48, 51, 63, and 66