Organic Inquisition
By Kevin Burgess
A complete online e‑workbook with questions, answers, tips, and explanatory videos covering introductory organic chemistry concepts, mechanisms and reactions with minimal memorization.
strategies to learn
Strategies to learn difficult subjects involve similar strategies. Understanding concepts comes first. Memorization becomes much easier when it is clear why facts are important, and how they interlock. Then what seemed to be random words begin to flow like poetry. Concepts must be introduced in logical sequences. It is impossible for beginners to design these sequences well; learning materials (eg texts, diagrams, and videos) composed by experts and competent instructors must show the way.
Superficial grasp of concepts create illusions of competence: understanding in theory but not practice. No one learns to swim or make love by being told; exploration is essential. Exploratory investigation should be appropriate. Too challenging leads to discouragement, too trivial to boredom, and both cause people to give up.
Beginners should have immediate feedback after each step. Texts can provide this via continual breaks for explanations and ideal solutions, like face-to-face tutors.
To obtain mastery, exploratory tests should be revisited at intervals, prioritizing ones found to be difficult first time. Revision via spaced repetition encourages the brain to shift concepts and memories from regions encoding for short term relevance (passing thoughts) to ones for long-term, frequent use. Repetition intervals should include sleep and be progressively longer until applied competence becomes intuitive.
contents outline
1 Fundamental Concepts
Fundamental principles vital to any introductory chemistry course.
2 Introductory Mechanisms
Nucleophilic substitutions; additions to alkenes, alkynes and benzene; and, an introduction to oxidation states.
3 Spectrometry And Spectroscopy
Mass spectrometry, ultraviolet absorption and fluorescence, infra-red (IR), ¹³C nucelar magnetic resonance (NMR), ¹H NMR, and problem solving.
4 Additions To Aldehydes / Ketones And Carbohydrates
Acetals and ketals: cyanohydrins, imines, enamines, nitriles and isonitriles; monosaccharides, and di- oligo- and polysaccharides.
5 Heterocycles And Nucleic Acids
Heterocyclic aromaticity, nucleic acids, DNA synthesis and sequencing, DNA analysis and editing.
6 Esters, Lipids, Amides, Amino Acids, Peptides And Proteins
Ester formation and hydrolyses; lipids; amide hydrolyses and dehydration, activation of carboxylic acids and acylation, amino acids, peptides, peptidesyntheses, and proteins.
about Dr. Kevin Burgess
Kevin Burgess, Gradipore Chair of Chemistry at Texas A&M University, has taught organic chemistry to graduates and undergraduates for more than thirty years. He has had a diversity of interests including organometallic catalysis, fluorescent dyes, peptidomimetics and medicinal chemistry. He has published ~360 research papers and ~13 patents.
Dr Burgess’ research now focuses on small molecules interacting with protein surfaces. He introduced the concept of universal peptidomimetics, and developed from that a suite of techniques first based on Exploring Key Orientations, then on Backbone Matching: a new approach for design of small molecules to perturb protein-protein interactions by using crystallographic information on protein-protein interactions (PPIs) to filter user-generated virtual libraries of cyclo-organopeptides. cyclo-Organopeptides are peptidic macrocycles encompassing an endocyclic organic part. His group have designed chemotypes of this kind for targeting cell surface receptors, particularly in the Trk series. Potential applications of this work are in diagnostics, imaging, and therapeutics. The molecule D3 he designed to bind the TrkA receptor reached phase III clinical trials for treatment of dry-eye disease. Much of his work involves fluorescent dyes. The Burgess Group has published extensively on BODIPY structures, and on the mode of action and applications of tumor-seeking cyanine dyes. Recently members made cyclo-organopeptides where the organic part is a fluorophore. Binding of these cyclo-fluoropeptides to cell surface receptors in live cells can be directly observed and quantified, and their intracellular locations tracked.
Professor Burgess edited, Solid Phase Syntheses, and authored a graduate workbook of problems and answers called Organic Chemistry By Inquisition. This is now republished online as Organic Reactions By Inquisition. Two introductory organic chemistry workbooks Organic Chemistry By Inquisition1 and 2 are available as hard copies. A second edition of these are being published as animated eworkbooks (problems with embedded videos) online. All the online books are available via Book (Apple), the Kindle app, and VitalSource.
Dr Burgess authored the Biomedical Chemistry section of Highlights in Chemistry and Industry 1985 – 2022. Instead, he now has an active YouTube channel, @kevinburgess1183, hosting over 145 videos for graduate and undergraduate chemistry, and on psychology, particularly of learning and teaching.
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