Chem 334 - Fall 2001
Organic Chemistry I

Dr. Carl C. Wamser

Chapter 4 Notes: Alcohols and Alkyl Halides

Functional groups

alkyl halide: R-X (X = halogen atom)

alcohol: R-O-H (hydroxyl group)

Functional Group Classification

Alkyl Halide Nomenclature

Alcohol Nomenclature

Alcohol Examples

cyclohexyl alcohol or cyclohexanol


Structure of Alcohols

Boiling Points of Alkyl Halides

Polarity of Alkyl Halides

Hydrogen Bonding

Effects of H-Bonding

Review of Acid-Base Reactions

Bronsted-Lowry Acid/Base

Acidity Constant (Ka)

usually simplified to
HA <==> H+ + A-

Acid Strength (pKa)

pH and pKa

Structural Effects on Acid Strength

Acid-Base Reactions

CH3COOH + OH- <==> CH3COO- + H2O
acid (pKa = 5) + base <==> base + acid (pKa = 15.7)
reaction favored for stronger acid

reaction favored to the right

Lewis Acids

Acid-Base Reactions of Alcohols

Mechanism of Proton Transfer - Potential energy diagram

Acidity of Alcohols

Substitution Reactions with HX - SN1 Mechanism



Hammond's Postulate

Substitution Reactions with HX - SN2 Mechanism

Halogen Substitution with Other Reagents

Halogenation of Alkanes

Free Radicals

Mechanism - Chain initiation

Mechanism - Chain propagation

Mechanism - Chain termination


Halogenation of Larger Alkanes


Hammond's Postulate

Radical stability