Chem 335 - Winter 2000
Organic Chemistry II

Dr. Carl C. Wamser

Chapter 15 - Carbonyl Compounds

Carbonyl Functional Groups

usually subdivided into two families:

The Carbonyl Group - Structure and Properties

Aldehyde Nomenclature


Ketone Nomenclature

acyl- as prefix
e.g., acetyl or benzoyl, as in acetylcyclopropane

Precedence Order of Functional Groups

Characteristic Properties

Nucleophilic Addition to Carbonyls

the major reaction of carbonyl compounds

General Trends:

C nucleophiles: CN-, RLi, RMgX, ylids

O nucleophiles: OH-, H2O, ROH

S nucleophiles: RSH

N nucleophiles: NH3, RNH2 , NH2OH, RNHNH2

H nucleophiles: LiAlH4, NaBH4

Acid Catalysis of Nucleophilic Addition

Hydration Reactions

Hydration is a reversible equilibrium

Base-Catalyzed Hydration

Acid-Catalyzed Hydration

Comparison of acid and base catalytic effects

Alcohol Additions

Acetals as protecting groups

Sulfur Additions - 1,3-Dithianes

Amine Additions

Carbon Additions

Wittig Reactions

Keto-Enol Tautomerism

Alpha-Substitution Reactions

Reduction Reactions

Oxidation of Aldehydes

Oxidation of Ketones

Glucose Hemiacetals

Glucose Acetal Polymers (Starches and Cellulose)