Chemistry 345 (2) Spring 1997

Structure determination using spectroscopic methods
UV-visible spectra (Table 14.3) and conjugated systems
Mass spectra and M+
IR spectra (Table 12.1) and functional groups

Fundamentals of proton nmr Proton equivalence
Chemical shift d (Table 13.4); ppm and hz
Integration to count hydrogens
Spin-spin splitting patterns and the n+1 rule
Coupling constant J (hz)

Assigned problems: Chapter 12: 16, 17, 20-22, 24, 31, 38. Chapter 13: 21, 23, 24, 28-36, 39-42, 58

Chapter 17, Alcohols and thiols
Structure and nomenclature, classification (1· 2· 3·)
Properties: Hydrogen bonding and boiling point
Acidity and pKa, alkoxides; basicity
Spectral recognition of simple alcohols
Preparation: From alkenes (review) ;
Reduction of carbonyl compounds
Grignard addition (RMgX) to carbonyl compounds
Reactions: Acid catalyzed dehydration to alkenes
SN1 and SN2 reactions using a better leaving group
Oxidation with Cr+6
TMS ether as a protecting group
Comparison with thiols and phenols

Assigned problems: 22-41, 44

Chapter 18, Ethers, epoxides and sulfides
Structure and nomenclature, epoxides, crown ethers
Properties: Comparison with alcohols
Spectral recognition of simple ethers
Preparation: Williamson (SN2)synthesis
Oxymercuration-reduction in ROH
Reactions: Acid cleavage with HBr or HI
Peroxide formation
Epoxides: Preparation and reactions
Sulfides: Preparation (SN2) and reactions

Assigned problems: 19-22, 24, 26-31, 33, 35, 37, 42