Organic Chemistry I
The structure, shape and reactions of carbon compounds: why carbon forms so many compounds, the history of structural theory from Wöhler and Kekulé to van 't Hoff, degrees of unsaturation and isomerism, formal charge, hybridization, polar bonds and resonance, skeletal formulas, functional groups and IUPAC nomenclature, pKa and the structural factors that control acidity and basicity, the conformations of alkanes and the cyclohexane chair with A-values and ring strain, radical halogenation, chirality, the Cahn–Ingold–Prelog rules for R/S and E/Z, diastereomers, meso compounds, optical activity, enantiomeric excess and resolution, curved-arrow mechanisms, nucleophiles and electrophiles, energy diagrams, the Eyring equation and the Hammond postulate, the SN2 and SN1 substitutions and the E2 and E1 eliminations with their stereochemistry and competition, alkene stability and electrophilic addition with Markovnikov's rule, carbocation rearrangements and halonium ions, and a capstone on hydroboration, hydrogenation, epoxidation, dihydroxylation, ozonolysis, polymerization, the chemistry of alkynes and acetylide ions, and retrosynthetic planning of multistep syntheses.
CHEM-261 Year 2 3 credits 12 lessons · 4 h 39 min ▶ Video lessons coming soon
Offered by HSM University · Chemistry
This is the Canadian version of this course. See the American version.
What you'll learn
- Explain what makes carbon unique, trace the origins of structural organic chemistry, calculate degrees of unsaturation and distinguish constitutional isomers from stereoisomers.
- Assign formal charges, hybridization and geometry to atoms in organic structures, draw and rank resonance forms, and use electronegativity and delocalization to locate electron-rich and electron-poor sites.
- Draw and interpret skeletal, condensed and three-dimensional formulas, recognize the common functional groups and their oxidation levels, and name organic compounds by the IUPAC rules.
- Use pKa values to predict the position of acid–base equilibria, explain acidity and basicity with atom, resonance, inductive, hybridization and solvation effects, and apply acid–base reactions to extraction.
- Analyse the conformations of alkanes and cyclohexanes with Newman projections and chair drawings, calculate conformer populations from energy differences and A-values, and explain ring strain and radical halogenation selectivity.
- Identify stereocentres and chiral molecules, assign R/S and E/Z descriptors with the Cahn–Ingold–Prelog rules, and explain why enantiomers can differ in biological activity.
- Relate stereoisomers with several stereocentres as enantiomers, diastereomers or meso compounds, calculate specific rotation and enantiomeric excess, and describe methods of resolution.
- Write mechanisms with correct curved arrows, identify nucleophiles and electrophiles, interpret energy diagrams, and relate free energies of activation and reaction to rates, equilibria and selectivity with the Hammond postulate.
- Describe the SN2 and SN1 mechanisms, their rate laws, stereochemistry and dependence on substrate, nucleophile, leaving group and solvent, and use substitution reactions in synthesis.
- Describe the E2 and E1 mechanisms, apply the anti-periplanar requirement and the Zaitsev and Hofmann rules, and predict whether substitution or elimination will dominate.
- Explain alkene stability and the mechanism of electrophilic addition, apply Markovnikov's rule, predict carbocation rearrangements, and describe additions of hydrogen halides, water and halogens with their stereochemistry.
- Describe hydroboration–oxidation, hydrogenation, oxidations and polymerization of alkenes, the reactions of alkynes and acetylide ions, and plan multistep syntheses with retrosynthetic analysis.
Course content
12 lessons · 4 h 39 min total · final exam
- 1 What organic chemistry is: carbon, structure and function 25 min · quiz
- 2 Structure and bonding: hybridization, resonance and formal charge 23 min · quiz
- 3 Drawing and naming organic molecules: functional groups and IUPAC nomenclature 27 min · quiz
- 4 Acids and bases in organic chemistry: pKa, structure and reactivity 23 min · quiz
- 5 Alkanes and cycloalkanes: conformations, strain and Newman projections 22 min · quiz
- 6 Stereochemistry I: chirality, enantiomers and the R/S system 23 min · quiz
- 7 Stereochemistry II: diastereomers, meso compounds, optical activity and resolution 22 min · quiz
- 8 Reaction mechanisms: curved arrows, energy diagrams and intermediates 23 min · quiz
- 9 Nucleophilic substitution: SN2 and SN1 23 min · quiz
- 10 Elimination: E2 and E1, and the competition with substitution 22 min · quiz
- 11 Alkenes I: structure, stability and electrophilic addition 23 min · quiz
- 12 Capstone: alkenes II and alkynes — hydroboration, oxidation, polymerization and synthesis planning 23 min · quiz
- E Final exam 20 questions
Requirements
Recommended background. You can start any course at any time.
Description
The structure, shape and reactions of carbon compounds: why carbon forms so many compounds, the history of structural theory from Wöhler and Kekulé to van 't Hoff, degrees of unsaturation and isomerism, formal charge, hybridization, polar bonds and resonance, skeletal formulas, functional groups and IUPAC nomenclature, pKa and the structural factors that control acidity and basicity, the conformations of alkanes and the cyclohexane chair with A-values and ring strain, radical halogenation, chirality, the Cahn–Ingold–Prelog rules for R/S and E/Z, diastereomers, meso compounds, optical activity, enantiomeric excess and resolution, curved-arrow mechanisms, nucleophiles and electrophiles, energy diagrams, the Eyring equation and the Hammond postulate, the SN2 and SN1 substitutions and the E2 and E1 eliminations with their stereochemistry and competition, alkene stability and electrophilic addition with Markovnikov's rule, carbocation rearrangements and halonium ions, and a capstone on hydroboration, hydrogenation, epoxidation, dihydroxylation, ozonolysis, polymerization, the chemistry of alkynes and acetylide ions, and retrosynthetic planning of multistep syntheses.
Part of the Science stream, typically taken in year 2.