Table of Contents

Introduction. ORG-04
GAMSAT ORGANIC CHEMISTRY
Chapter 1. Molecular Structure of Organic Compounds. . . . . . . . . . . . . . . . .ORG-13
1.0 GAMSAT has a Need for Speed!. ORG-14
1.1 Carbon: The Centre of our World. ORG-18
1.1.1 Overview: A Closer Look at the Atoms of Organic Chemistry. . . . .ORG-23
1.2 Hybrid Orbitals. ORG-24
1.3 Bonding. ORG-25
1.3.1 The Effects of Multiple Bonds. ORG-26
1.4 Delocalised Electrons and Resonance. ORG-26
1.5 Lewis Structures, Charge Separation and Dipole Moments. ORG-27
1.5.1 Strength of Polar vs. Non-Polar Bonds. ORG-30
1.6 Ground Rules. ORG-31
1.6.1 Primary, Secondary, Tertiary, and Quaternary
Carbons and Molecules . ORG-33
1.6.2 Exercise: Introduction to Identifying Functional Groups. ORG-33
1.7 Drawing Molecular Structures of Organic Compounds. ORG-35
1.8 Pattern Recognition, Geometric Reasoning and
Problem-based Learning . ORG-41
Chapter 2. Stereochemistry. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ORG-59
2.0 GAMSAT has a Need for Speed!. ORG-60
2.1 Isomers. ORG-62
2.1.1 Structural (Constitutional) Isomers. ORG-62
2.2 Spatial/Stereoisomers. ORG-63
2.2.1 Geometric Isomers cis/trans, E/Z. ORG-63
2.2.2 Enantiomers and Diastereomers. ORG-64
2.3 Absolute and Relative Configuration. ORG-65
2.3.1 The R, S System and Fischer Projections . ORG-66
2.3.2 Optical Isomers. ORG-69
2.3.3 Meso Compounds. ORG-70
2.4 Conformational Isomers. ORG-71
Chapter 2: Gold Standard Foundational GAMSAT Practice Questions. ORG-75
Chapter 2: Gold Standard GAMSAT-Level Practice Questions. ORG-76
Chapter 3. Alkanes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ORG-83
3.0 GAMSAT has a Need for Speed!. ORG-84
3.1 Description and Nomenclature. ORG-85
3.1.1 Bicycloalkanes: Examples of Isomeric C8H14 . ORG-87
3.1.2 Foundational Nomenclature Exercises: Alkanes. ORG-87
3.1.3 Physical Properties of Alkanes. ORG-89
-vi3.2
Important Reactions of Alkanes. ORG-89
3.2.1 Combustion. ORG-89
3.2.2 Radical Substitution Reactions. ORG-90
3.3 Ring Strain in Cyclic Alkanes. ORG-91
Chapter 3: Gold Standard GAMSAT-Level Practice Questions. ORG-94
Chapter 4. Alkenes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ORG-99
4.0 GAMSAT has a Need for Speed!. ORG-100
4.1 Description and Nomenclature. ORG-101
4.1.1 Foundational Nomenclature Exercises: Alkenes and Alkynes . ORG-103
4.2 Important Chemical Reactions. ORG-105
4.2.1 Electrophilic Addition. ORG-105
4.2.2 Oxidation. ORG-110
4.2.3 Hydrogenation. ORG-112
4.2.4 The Diels–Alder Reaction. ORG-112
4.2.5 Resonance Revisited . ORG-114
4.3 Alkynes. ORG-115
Chapter 4: Gold Standard Foundational GAMSAT Practice Questions. ORG-117
Chapter 4: Gold Standard GAMSAT-Level Practice Questions. ORG-118
Chapter 5. Aromatics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .ORG-127
5.1 Description and Nomenclature. ORG-128
5.1.1 Hückel’s Rule . ORG-129
5.2 Electrophilic Aromatic Substitution. ORG-131
5.2.1 O-P Directors . ORG-133
5.2.2 Meta Directors. ORG-134
5.2.3 Reactions with the Alkylbenzene Side Chain. ORG-135
Chapter 5: Gold Standard Foundational GAMSAT Practice Questions. ORG-136
Chapter 5: Gold Standard GAMSAT-Level Practice Questions. ORG-137
Chapter 6. Alcohols. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ORG-145
6.0 GAMSAT has a Need for Speed!. ORG-146
6.1 Description and Nomenclature. ORG-148
6.1.1 Foundational Nomenclature Exercises: Alcohols. ORG-149
6.1.2 Acidity and Basicity of Alcohols . ORG-150
6.1.3 Synthesis of Alcohols: How to Make Alcohols . ORG-151
6.2 Important Reactions of Alcohols. ORG-153
6.2.1 Dehydration. ORG-153
6.2.2 Oxidation-Reduction. ORG-154
6.2.3 Substitution. ORG-154
6.2.4 Elimination. ORG-156
6.2.5 Conversion of Alcohols to Alkyl Halides. ORG-157
Chapter 6: Gold Standard Foundational GAMSAT Practice Questions. ORG-159
Chapter 6: Gold Standard GAMSAT-Level Practice Questions. ORG-161
GOLD STANDARD GAMSAT ORG-01
Chapter 7. Aldehydes and Ketones. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .ORG-171
7.1 Description and Nomenclature. ORG-172
7.1.1 Foundational Nomenclature Exercises:
Aldehydes and Ketones . ORG-174
7.2 Important Reactions of Aldehydes & Ketones . ORG-175
7.2.1 Overview. ORG-175
7.2.2 Acetal (ketal) and Hemiacetal (hemiketal) Formation. ORG-177
7.2.3 Imine and Enamine Formation . ORG-178
7.2.4 Aldol Condensation. ORG-179
7.2.5 Conjugate Addition to α-β Unsaturated Carbonyls. ORG-180
Chapter 7: Gold Standard Foundational GAMSAT Practice Questions. ORG-182
Chapter 7: Gold Standard GAMSAT-Level Practice Questions. ORG-184
Chapter 8. Carboxylic Acids. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .ORG-191
8.1 Description and Nomenclature. ORG-192
8.1.1 Foundational Nomenclature Exercises: Carboxylic Acids. ORG-194
8.1.2 Carboxylic Acid Formation . ORG-195
8.2 Important Reactions of Carboxylic Acids . ORG-196
Chapter 8: Gold Standard Foundational GAMSAT Practice Questions. ORG-199
Chapter 8: Gold Standard GAMSAT-Level Practice Questions. ORG-199
Chapter 9. Carboxylic Acid Derivatives . . . . . . . . . . . . . . . . . . . . . . . . . . . . ORG-205
9.1 Acid Halides. ORG-206
9.1.1 Acid Anhydrides . ORG-206
9.2 Important Reactions of Carboxylic Acid Derivatives. ORG-207
9.3 Amides. ORG-209
9.3.1 Important Reactions of Amides. ORG-210
9.4 Esters. ORG-210
9.4.1 Fats, Glycerides and Saponification. ORG-213
9.5 β-Keto Acids. ORG-213
9.6 Relative Reactivity of Carboxylic Acid Derivatives. ORG-214
9.7 Phosphate Esters. ORG-214
Chapter 9: Gold Standard Foundational GAMSAT Practice Questions. ORG-215
Chapter 9: Gold Standard GAMSAT-Level Practice Questions. ORG-217
Chapter 10. Ethers and Phenols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ORG-223
10.1 Description and Nomenclature of Ethers . ORG-224
10.1.1 Important Reactions of Ethers. . . . . . . . . . . . . . . . . . . . . . . . . . . .ORG-224
10.2 Phenols. ORG-226
10.2.1 Electrophilic Aromatic Substitution for Phenols. ORG-227
Chapter 10: Gold Standard Foundational GAMSAT Practice Questions. ORG-228
Chapter 10: Gold Standard GAMSAT-Level Practice Questions. ORG-229
ORG-02 INTRODUCTION TO ORGANIC CHEMISTRY
Chapter 11. Amines. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ORG-235
11.1 Description and Nomenclature. ORG-236
11.1.1 The Basicity of Amines. ORG-237
11.1.2 More Properties of Amines. ORG-238
11.2 Important Reactions of Amines. ORG-239
Chapter 11: Gold Standard Foundational GAMSAT Practice Questions. ORG-242
Chapter 11: Gold Standard GAMSAT-Level Practice Questions. ORG-244
Chapter 12. Biological Molecules . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ORG-251
12.1 Amino Acids. ORG-252
12.1.1 Hydrophilic vs. Hydrophobic. ORG-253
12.1.2 Acidic vs. Basic. ORG-254
12.1.3 The 20 Alpha-Amino Acids. ORG-255
12.2 Proteins. ORG-257
12.2.1 General Principles. ORG-257
12.2.2 Protein Structure. ORG-258
12.2.3 Protein Function and Detection. ORG-261
12.3 Carbohydrates . ORG-261
12.3.1 Description and Nomenclature. ORG-261
12.3.2 Important Reactions of Carbohydrates. ORG-265
12.3.3 Polysaccharides. ORG-268
12.4 Lipids. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .ORG-270
12.4.1 Steroids. ORG-274
12.4.2 Lipoproteins. ORG-275
12.5 Phosphorous in Biological Molecules. ORG-275
Chapter 12: Gold Standard GAMSAT-Level Practice Questions. ORG-277
Chapter 13. Separations and Purifications. . . . . . . . . . . . . . . . . . . . . . . . . . ORG-295
13.1 Separation Techniques. ORG-296
13.2 Chromatography. ORG-298
13.2.1 Gas-Liquid Chromatography. ORG-298
13.2.2 Thin-Layer Chromatography. ORG-298
13.2.3 Paper chromatography: Conventional and 2D . ORG-300
13.2.4 Column Chromatography . ORG-301
13.3 Gel Electrophoresis . ORG-301
13.4 Recrystallisation. ORG-302
Chapter 14. Spectroscopy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ORG-305
14.1 IR Spectroscopy. ORG-306
14.2 Proton NMR Spectroscopy. ORG-307
14.2.1 Deuterium Exchange. ORG-310
14.2.2 13C NMR. ORG-310
14.3 Mass Spectrometry. ORG-311
GOLD STANDARD GAMSAT ORG-03

About the Author

Dr. Ferdinand was awarded numerous scholarships en route to graduating with honours in a BSc programme. After medical school, he wrote several award-winning textbooks. For over 10 years, he has given GAMSAT seminars on campuses across Australia, Ireland and the UK. He is known as a dynamic lecturer who can simplify complex topics.