Text: Course Outline
or
Organic Chemistry, 9th edition, T. W. Graham Solomons and Craig B. Fryhle, John Wiley & Sons, Inc., New York, 2006.
Solomons
o
What is organic
chemistry and why is it so
important?
1.1 – 1.2
o
What do I know
from High School? The chemistry
o
of
aldehydes and ketones!
o
Models of
chemical bonding
1.3 – 1.4
§
Ionic bonds
1.4A
§
Covalent bonds
1.4B
o
Lewis structures
1.5
o
Formal charge
1.7
o
Resonance
1.8
§
Quantum mechanics
1.9
o
Atomic
orbitals and electron configurations
1.10
o
Molecular
orbitals
1.11
o
Hybridization
1.12 – 1.17
o
Functional
groups and classification of organic
compounds
2.1 – 2.2, 2.5 – 2.13
o
Bond energies
and bond breaking
3.3, 10.2
o
Curved arrow
conventions
3.4
o
Bond polarity
and polarity of molecules
2.3 - 2.4
o
Polarity and
physical characteristics
2.14
o
Criteria of
purity - physical properties and molecular
structure
o
Structure
determination - infrared spectroscopy
2.16
2.
Introduction to
organic reactions:
acids
and bases
3
o
Reaction types
3.1
o
Acid – base
reactions
3.2
§
Bronsted-Lowry
acids and bases
3.2A
§
Lewis acids and bases
3.2B
o
Strengths of
acids and bases – Ka and Kb
3.5
o
Predicting the
result of acid – base reactions
3.6
§
Structure and acidity
3.7
§
Effects of hybridization
3.7A
§
Inductive effects
3.7B
o
Stability and
potential energy
3.8
o
Free energy,
entropy, and enthalpy
3.9
o
Acidity of
carboxylic acids
3.10
3.
Alkanes and
cycloalkanes: nomenclature,
conformational
analysis, and introduction to
synthesis
4
o
Introduction
4.1
o
Structure
4.2
o
Conformations
4.8 – 4.9
o
Nomenclature of
alkanes, alkyl halides, and
alcohols
4.3
o
Nomenclature of
cycloalkanes
4.4
o
Nomenclature of
alkenes and cycloalkanes
4.5
o
Nomenclature of
alkynes
4.6
o
Cycloalkanes –
ring strain
4.10 – 4.11
o
Conformations of
cyclohexane
4.12
o
Monosubstituted
cyclohexanes
4.13
o
Disubstituted
cyclohexanes – cis –
trans
isomerism
4.14
o
Synthesis of
alkanes and cycloalkanes
4.17
§
Hydrogenation of alkenes and alkynes
4.17A
§
Reduction of alkyl halides
4.17B
§
Alkylation
of terminal alkynes
4.17C
§
The Corey – Posner – Whitesides –
House
synthesis
12.9
o
Introduction to
organic synthesis
4.18 – 4.19
o
Reactions of
alkanes with halogens
10.3
§
Mechanism of chlorination
10.4 – 10.6
4.
Stereochemistry
5
o
Introduction
5.1
o
Constitutional
isomers
5.2
o
Enantiomers and
chiral molecules
5.3, 5.6
o
Historical
origin of stereochemistry
5.5
o
Configurations -
the R/S system
5.7
o
Properties of
enantiomers - optical activity
5.8
o
Racemic mixtures
5.9
o
Synthesis of
chiral molecules
5.10 – 5.11
o
Molecules with
more than one stereogenic centre
5.12 – 5.13
§
Meso
compounds
5.12A
o
Stereoisomerism
of cyclic compounds
5.14
o
Relating
configurations
5.15
o
Racemic mixtures
and their resolution
5.16
5.
Alkyl halides
6
o
Introduction
6.1
o
Preparation of
halides:
§
from alcohols
11.7
§
from alkanes
10.3
§
from alkenes
8.2, 8.12
§
iodides
o
Nucleophilic
substitution reactions
6.2
§
Nucleophiles
6.3
§
Leaving groups
6.4
§
The SN2 kinetcs
6.5
§
SN2 reaction mechanisms
6.6
o
Free-energy
diagrams
6.7
§
Stereochemical
consequences of an SN2
reaction
6.8
§
SN1 reaction mechanism
6.9 – 6.10
§
Carbocations
6.11
§
Carbocation rearrangements
7.8
§
Stereochemical
consequences of an SN1
reaction
6.12
§
Factors affecting the rates of SN reactions
6.13
§
Organic synthesis: functional group
transformation
using SN2 reactions
6.14
§
ROH + HX – an SN reaction
11.8
6.
Alkenes
7
o
Structure
7.1
o
Degree of
unsaturation
7.15
o
Nomenclature
4.5, 7.2
o
cis - trans isomers and the E/Z system
7.3
o
Cycloalkenes
7.4
o
Synthesis by
elimination reactions
7.5
·
dehydrohalogenation
of alkyl halides
6.15, 6.16, 6.17, 7.6
·
dehydration of alcohols
7.7, 7.8
·
debromination
of vicinal dibromides
·
hydrogenation of alkynes
7.14
o
Synthesis of
alkynes by elimination reactions
7.9
7.
Reactions of
alkenes and alkynes
8
o
Hydrogenation of
alkynes
7.14
o
Introduction to
addition reactions
8.1
o
Addition of HX
8.2, 8.3
o
Addition of
sulfuric acid
8.4
o
Addition of
water
8.5
o
Oxymercuration –
demercuration
8.6
o
Hydroboration
8.7 – 8.10
o
Addition of
halogens
8.12 – 8.13
o
Halohydrin
formation
8.14
o
Free radical
additions
10.9
o
Carbenes
8.15
o
Hydroxylation
8.16
o
Oxidation and
ozonolysis
8.17
o
Addition of
halogen to alkynes
8.18
o
Addition of HX
to alkynes
8.19
o
Synthesis
8.20
Solomons and Fryhle
1. Nuclear magnetic resonance spectroscopy 9
Introduction 9.1 - 9.2, 9.4
Nuclear spin 9.3
Spectrometers 9.3
Shielding effects 9.5
Chemical shifts 9.3C, 9.6, 9.7
Integration 9.3D
Spin-spin coupling 9.8
Interpretation and structural elucidation
2. Conjugated unsaturated systems 13, 13.1
Allylic substitution 13.2
Stability of the allyl radical 13.3 – 13.5
Dienes 13.6 – 13.8
1,2 and 1,4 addition 13.10
Diels-Alder reaction 13.11
3. Aromatic compounds 14, 15
Introduction 14.1
Nomenclature 14.2
Structure and stability of benzene 14.3 – 14.5
Molecular orbital description of benzene 14.6
Aromaticity and the Hückel Rule 14.6 – 14.9
Spectra of aromatic compounds 14.11
Electrophilic aromatic substitution 15.1 – 15.9
Substituent effects 15.10 – 15.11
Arene oxidation 15.13C
Planning a synthesis 15.14
4. Alcohols and ethers 11
Structure and nomenclature 11.1
Sterols 23.4
Physical properties 11.2
Synthesis
fermentation 11.3B
oxymercuration 11.4
hydroboration 11.4
reduction of carbonyl compounds 12.3
reduction of acids and esters 12.3
Grignard synthesis of alcohols 12.6 - 12.8
Reactions: 11.5, 12.1
acidity 11.6
acidity of phenols 21.5
reaction with HX, PX3 PX5, and SOCl2 11.7 – 11.9
tosylates 11.10
dehydration 7.7
Oxidation of alcohols 12.4
Synthesis of ethers 11.11
Reactions of ethers 11.12
Epoxides 11.13
Epoxides – ring opening 11.14
5. Aldehydes and Ketones 16
Structure 16.1
Nomenclature 16.2
Synthesis - aldehydes 16.4
Synthesis - ketones 16.5
Oxidation 16.12 – 16.13
Nucleophilic addition 16.6 -16.11
Cannizzaro reaction
Spectroscopy 16.14
6. Aldol reactions 17
Acidity of µ-hydrogens 17.1
Keto - enol tautomerism 17.2
Halogenation of ketones and aldehydes 17.3B
Haloform reaction 17.3C
Aldol condensation 17.4
Crossed aldol condensation 17.5
Cyclizations via aldol condensations 17.6
7. Carboxylic acids 18
Structure 18.1
Nomenclature 18.2
Physical properties 18.2
Acidity 18.2C
Salts 18.2B
Preparation of carboxylic acids 18.3
Nitriles 18.8H
Nucleophilic acyl substitution 18.4
Acyl chlorides 18.5
Anhydrides 18.6
Esters 18.7
Amides 18.8
Hell-Volhard-Zelinski reaction
Spectroscopic properties
8. Lipids 23
Oils and fats 23.2
Saponification 23.2C
Hardening of oils 23.2A
Soaps and detergents 23.2
Phospholipids 23.6
Waxes 23.7
9. Amines 20
Structure 20.2B
Nomenclature 20.1
Physical properties 20.2A
Preparation 20.5
Basicity 20.3
Reactions of amines 20.6
Reactions with nitrous acid 20.7, 20.8
Dyes 20.9
Reactions with sulfonyl chlorides 20.10, 20.11
Spectroscopic analysis 20.12
10. Carbohydrates 22
Introduction 22.1
Photosynthesis 22.1B
Structure of monosaccharides 22.2, 22.6, 22.11
Mutarotation 22.3
Osazones 22.8
Glycosides 22.4
Synthesis and degradation 22.9
Disaccharides 22.12
Polysaccharides 22.13
11. Amino acids, peptides and proteins 24
Structure 24.2
Zwitterions 24.2C
Isoelectric points 24.2C
Synthesis 24.3
Peptides 24.1
Amino acid sequencing 24.4 - 24.6
Peptide synthesis 24.7
Proteins 24.8