This is part one of a comprehensive second-year organic chemistry course suitable for those majoring in chemistry and biochemistry. It may also be appropriate for students in biology and those interested in pursuing health-related professional programs. It begins with a brief review of bonding, followed by review of organic functional groups, and the role of acids and bases in organic chemistry. Theory and application of I.R. spectroscopy and U.V. spectroscopy are studied. Alkane conformation is reviewed and cycloalkanes are introduced. Chirality is discussed along with stereoisomerism and R/S stereocentre configurations. Nomenclature and reactivity of organic halides and derivatives, substituted cycloalkanes, alkenes, alkynes, alcohols, ethers, and epoxides are covered throughout the course. Reactions are approached from a mechanistic point of view with an emphasis on underlying reactivity and application in organic synthesis.
Chemical Bonding - Review: Importance of carbon in organic chemistry. Types of chemical bonds - ionic, covalent, polar covalent. Covalent Bonding and Molecular Shape Theories: Lewis, VSEPR, Valence Bond, Molecular Orbital.
Isomerism and Functional Group Overview - Review: Representation of structural formulas. Isomerism - definition, types, nomenclature. General formulas and structures of the following functional groups - Hydrocarbons, Alkenes, Alkynes, Akyl Halides, Alcohols, Ethers, Amines, Aldehydes, Ketones, Carboxylic Acids, Amides and Esters. Molecules with de-localized electrons, drawing resonance structures, determining strucutres significant to a resonance hybrid.
Introduction to I.R. and U.V. Spectroscopy:Physical principles. Experiment design. Spectra interpretation.
Acids and Bases in Organic Chemistry: Bronsted/Lowry and Lewis Acid/Base theories - background, definitions, examples, and identification of common acids and bases. Use of curved arrows in Organic Chemistry and reaction mechanisms. Organic compound acidity as a function of conjugate base structure. Ranking organic compound acidity, predicting the direction of organic acid/base equilibria.
Alkanes and Cycloalkanes - Conformational Analysis:Review of Newman projections and corresponding potential energy diagrams of alkanes. Relative stabilities, conformations, and ring strain in cyclopropane, cylobutane and cyclopentane. Chair and boat forms of cyclohexane. Conformational analysis of substituted cyclohexanes.
Stereoisomerism: Concept of chirality - non-superimposable mirror images. Enantiomers and diastereomers - definition, recognition, drawing, differences in physical and chemical properties. Meso compounds. Cahn-Ingold-Prelog R/S system of naming chiral centres. E/Z System for naming alkene diastereomers. Optical activity - methods of determination, theory, specific rotation, optical purity, enantiomeric excess. Fischer projection drawings.
Organic Reactivity and Mechanisms: Introduction to thermodynanmics and kinetics as they relate to organic reaction mechanisms. Reaction potential energy plots - reactants, products, intermediates, transition states, relating energy plots to mechanisms. Nucleophiles and electrophiles - recognizing reaction roles. Communicating organic reaction mechanisms with curved arrows. Classifying arrow pushing patterns. Carbocation stability and rearrangement.
Nucleophilic Substitution Reactions (reactivity of alkyl halides/derivatives): Naming alkyl halides. SN2 reactions - mechanism, transition state, stereochemical outcomes, reaction kinetics. SNl reactions - mechanism, carbocation stability, stereochemical outcomes, kinetics. Factors affecting rates and outcomes of SNl and SN2 reactions - substrates, strong/weak nucleophiles, concentration, temperature, solvent.
Elimination Reactions: Naming alkenes. Alkene stability. E2 reactions - substrates, bases, kinetics, regioselectivity, stereochemical outcomes. E1 reactions - substrates, bases, kinetics, carbocation intermediates, regioselectivity, stereochemical outcomes. Zaitsev's Rule. Determining E2 or E1 mechanism/strong and weak bases. Predicting a substitution/elimination mechanism and products.
Alkene Addition Reactions: Bonding in alkenes. Pi electrons as nucleophiles. Markovnikov's Rule. Hydrohalogenation. Acid-catalyzed hydration. Oxymercuration-demercuration. Hydroboration-oxidation. Catalytic hydrogenation. Halogenation. Halohydrin reactions. Dihydroxylation. Ozonolysis. Introduction to organic synthesis/retrosynthesis.
Alkynes: Bonding in alkynes. Naming alkynes. Alkyne synthesis via elimination. Alkyne reduction with hydrogen - catalysts, stereochemical outcomes. Acid catalyzed hydration, Hydroboration-oxidation. Halogenation. Alkynes in synthesis - de-protonated alkynes as nucleophiles to make carbon-carbon bonds.
Alcohols/Phenol and Ethers: Alcohol bonding and naming, including phenols. Alcohol acidity and physical properties. Converting alcohols into leaving groups - mesylates, tosylates, and alkyl halides, including stereochemical implications. Converting alcohols/phenol to ethers via the Williamson ether synthesis. Ether structure and naming. Cleaving ethers with strong acid. Synthesizing epoxides from alkenes. Reactions of ethers and epoxides including ring opening reactions of epoxides. Regiochemistry of reaction on unsymmetrical expoxides.
The laboratory experiments will be selected from the following list and performed during the lab period:
- Simple and Fractional Distillation of an Acetone/Water Mixture
- Melting Point Determination
- Extraction and Purification of Impure Organic Compounds (Two Weeks)
- Isolation of Eugenol and Eugenol Acetate from Oil of Cloves (Two Weeks)
- Extraction of Caffeine from Tea Leaves
- Synthesis of 2-Chloro-2-methylbutane
- Practical Lab Exam
- Written Lab Exam
Methods of Instruction
The course will be presented using lectures, problem sessions, and class discussion. Videos, other audio-visual aids, as well as on-line material will be used where appropriate. The laboratory will be used to illustrate the practical aspects of the course material.
Means of Assessment
Evaluation will be carried out in accordance with Douglas College policy. The instructor will present a written course outline with specific evaluation criteria at the beginning of the semester. Evaluation will be based on the following:
Lecture Material (70%)
- Two or more in-class tests will be given during the semester (20-30%)
- Any, all, or none of the following evaluations, at the discretion of the Instructor: individual/group assignments, in-class/on-line assignments/quizzes, in-class presentations, class participation [5% maximum] (0-20%)
- A final exam covering the entire semester's work will be given during the final examination period (30-40%)
- Pre-lab work (typically evaluated with a notebook inspection and/or pre-lab quiz), written experiment reports (either formal reports or report sheets), qualitative/quantitative results of experiments performed on unknown samples
- Written quizzes in addition to the pre-lab work may be given, at the discretion of the instructor
- Final Lab Exam(s) (written and/or practical, at the discretion of the instructor)
A student who misses three or more laboratory experiments will earn a maximum P grade.
A student who achieves less than 50% in either the lecture or laboratory portion of the course will earn a maximum P grade.
Upon completion of this course, students will be able to:
- give the IUPAC name, or the common name, if one exists, when given the formula of an organic compound
- draw diagrams of all possible isomers, and describe each type of isomer when given the formula of an organic compound,
- name and identify the common functional groups
- describe relevant molecules in terms of a resonance hybrid by drawing all significant resonance structures and describing their respective contributions to such a hybrid
- list the types of intermolecular forces that apply to each molecule, predict which will have the higher boiling point, and describe the general solubility of each when given the formulas of two compounds
- predict the relative acidity (pKa) when given the structure of an organic compound based on the type of functional groups present and the structure of its conjugate base
- describe the general experiment design and underlying physical principles of I.R. and U.V. spectroscopy; given the I.R. spectrum of an unknown compound, determine the functional groups present; given the U.V. spectrum of an unknown compound, identify the presence of a conjugated system and identify the location of the absorption maximum
- draw the lowest and highest energy conformations of alkanes via Newman projections
- draw mono-/multi-substituted cyclohexanes in all relevant conformations, indicating axial/equatorial bonds and 1,3-diaxial interactions
- define and give examples of the types of ring strain found in cyclopropane through to cyclohexane
- identify the stereocentre using the R/S system of nomenclature
- draw molecules with one or more stereocentre(s), communicating the correct stereochemistry, using any of: Fischer projection, Newman projection, saw-horse projection, wedge/dash bonds on a zig-zag line-bond diagram; identify a meso compound
- desribe how to conduct an optical activity experiment using a polarimeter, and describe the conclusions in terms of observed rotation, specific rotation, optical purity, and enantiomeric excess
- define terms and give examples of reactions that are stereoselective, stereospecific, regioselective, and/or whether the reaction is under thermodynamic or kinetic control
- sketch a potential energy plot for a reaction, given the mechanism, including reactants, intermediates, transition states, and products; use a potential energy plot to describe relative reaction rate and relative stability of chemical species
- rank the relative stabilities of a given a list of carbocations, including the resonance stabilized carbocations
- identify strong nucleophiles, weak nucleophiles, electrophiles, strong bases, weak bases; describe their interactions by drawing reaction mechanisms including curved arrows
- provide the mechanism of either an SNl or SN2 substitution reaction indicating the structures of all transition states and intermediates, including the stereochemical outcome of the reaction
- provide the mechanism of either an El or E2 elimination reaction indicating the structures of all transition states and intermediates including dehydration reactions of alcohols
- predict the major product of a reaction including: competition between elimination and substitution, addition to alkenes/alkynes (hydrohalogenation, hydration, hydroboration-oxidation, halogenation, halohydrin reaction, dihydroxylation), ozonolysis of alkenes, catalytic hydrogenation, ring opening of epoxides, de-protonation and reaction of terminal alkynes and alcohols to produce new C-C and C-O bonds, conversion of alcohols into alkyl halides and derivatives
- complete the reaction and draw a complete mechanism to rationalize the products formed, including curved arrows, by-products, and intermediates when given a full or partial reaction
- utilize retrosynthesis, as necessary, to design a synthesis of a target compound using reactions learned throughout the course when given the structure of a desired synthetic target, and a list of allowed starting materials,
Below shows how this course and its credits transfer within the BC transfer system.
A course is considered university-transferable (UT) if it transfers to at least one of the five research universities in British Columbia: University of British Columbia; University of British Columbia-Okanagan; Simon Fraser University; University of Victoria; and the University of Northern British Columbia.
For more information on transfer visit the BC Transfer Guide and BCCAT websites.