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.
Spectroscopic Methods of Structure Determination: Electromagnetic spectrum. Brief review of U.V. spectroscopy and I.R. spectroscopy. Theory and application of 1H- and 13C-N.M.R. spectroscopy. Brief introduction to using mass spectrometry to determine a molecular ion. Combined structural problems.
Oxidation/Reduction Reactions of Alcohols/Carbonyl Compounds: Identifying oxidation and reduction in organic compounds. Reduction reactions on carbonyl compounds: lithium aluminum hydride, sodium borohydride, catalytic hydrogenation. Oxidation reactions on alcohols/carbonyl compounds: chromium reagents/derivatives. Selected modern oxidation methods (e.g. Swern oxidation). Grignard reactions with aldehydes, ketones, esters, carbon dioxide, and epoxides.
Radical Reactions: Differences between radical and ionic reactions and mechanisms. Single-barbed (fish-hook) arrows. Formation, stability, and reactions characteristic of radicals. Radical addition of halogen to alkanes. Anti-Markovnikov addition of HBr to alkenes. Radical polymerization. Introduction to synthetic polymers and structure-property relationships.
Conjugated Unsaturated Systems: Resonance structures and the allyl radical and cation. Allylic substitution reactions. Alkadienes and polyunsaturated hydrocarbons. Diels-Alder (1,4-cycloaddition) reactions.
Aromatic Compounds: Nomenclature of benzene derivatives. Structure and stability of benzene and selected additional aromatic compounds. Huckel’s Rule and criteria for aromaticity. Birch reduction.
Reactions on Benzene and Derivatives: Electrophilic aromatic substitution general mechanism. Electrophilic reactions on benzene: halogenation, nitration, sulfonation/de-sulfonation, Friedel-Crafts alkylation and acylation, Clemmenson Reduction. Substituent effects on reactivity and orientation, activating and deactivating groups. Nucleophilic aromatic substitution.
Aldehydes and Ketones and Addition Reactions to the Carbonyl Group: Aldehyde and ketone nomenclature. Physical properties. Synthesis of aldehydes and ketones. Nucleophilic addition to carbonyl group, Addition of carbon-based nucleophiles. Addition of oxygen nucleophiles: hydrates, hemiacetal and acetal formation. N-based nucleophiles: imine and enamine formation. Named addition reactions: Wolff-Kishner reduction, Wittig reaction, Baeyer-Villiger oxidation.
Aldol Reaction, Reactions at the a-Carbon: Identifying the carbonyl alpha-carbon. Keto-enol tautomerization. Reactions of enols and enolates, including alpha-halogenation and alpha-alkylation. The Aldol reaction, crossed Aldol reactions, Claisen-Schmidt reactions, crossed Claisen reactions, Dieckmann condensation. Cyclizations via Aldol condensations. Malonic ester synthesis. Conjugate addition reactions, Michael reaction. Stork enamine synthesis. Robinson annulation.
Carboxylic Acids and their Derivatives: Physical properties. Carboxylic acid and derivative nomenclature. Preparation and reactions of carboxylic acids, anhydrides, esters, amides, acid chlorides, amides, nitriles. Carboxylic acid derivative reactivity order. Nucleophilic substitution of carboxylic acid derivatives.
Amino Acids and Proteins: Classification and nomenclature. Acid-base properties. Peptide and disulfide bonds. Primary, secondary, tertiary, quaternary peptide structure.
Laboratory experiments will be selected from the following list and performed during the lab period:
- The Aldol Reaction (Two weeks)
- Combined Structural Problem Solving Session
- Identification of an Unknown Compound by Spectroscopy
- Separation and Identification of Methyl Esters of Fatty Acids by Gas Chromatography (Two Weeks)
- Grignard Reaction: Synthesis of Triphenylmethanol (Two weeks)
- Nitration of an Unknown Organic Compound (Two weeks)
- Polarimetry of Carbohydrates (Two Weeks)
- Esterification: Synthesis of an Unknown Ester
- Lab Exam(s) (any or all of: written/practical/oral presentation/oral quiz/group work)
Upon completion of this course, students will be able to:
- determine the structure of an unknown organic compound when given the formula, I.R. spectrum, U.V.-Vis. absorption spectrum, mass spectrum, 1H and 13C N.M.R. spectra
- predict the number of peaks and their respective chemical shifts, splitting patterns, and integrations in a 1H- N.M.R spectrum when given the structural formula of an organic compound
- recognize common oxidizing and reducing agents and identify the transformation they induce
- predict a radical reaction and its major product(s) by drawing an appropriate radical mechanism when given suitable substrate(s) and reagent(s)
- predict the relative stability when given a list of radical species
- predict the structure of the polymer and draw a mechanisn for the initiation, propogation, and termination steps of the radical reaction when given an appropriate monomer
- draw the resonance structures of allylic radicals and draw the complete mechanism of an allylic substitution reaction; predict whether an allylic substitution reaction will be thermodynamically or kinetically controlled
- predict the product of a Diels-Alder reaction (including stereochemical details) and the relative speed of the reaction when given a list of potential dienes and dienophiles
- give experimental evidence showing that benzene is resonance stabilized, and relate this evidence to molecular orbital theory
- predict whether any given organic compound is aromatic, non-aromatic, or anti-aromatic
- predict the structure of the major product when given benzene or a substituted aromatic and a suitable electrophile,by drawing a detailed reaction mechanism showing all resonance structures
- predict the structure of the major product when given a substituted aromatic and a suitable nucleophile, by drawing a detailed reaction mechanism
- predict if reaction will occur when given an aldehyde or ketone and a suitable reagent, by addition to the carbonyl group or at the carbon alpha to the carbonyl group
- give the IUPAC name and the common name, if one exists, when given the formula of an organic compound containing a functional group covered in the course,
- predict the major product when given substrate formula(s) and reagent(s), for all reactions covered in the course
- provide the complete mechanism for all reactions covered in the course by drawing curved arrows and indicating the structures of all transition states, intermediates, and by-products
- design a synthesis of the target compound using reactions learned throughout the course and CHEM 2321 when given the structure of a desired synthetic target, and a list of allowed starting materials,
- name any naturally-occuring amino acid, given its structure; draw any naturally-occuring amino acid, given its name
- draw an amino acid zwitter-ion; predict the acid/base properties of any amino acid, including the shape of its titration curve
- describe and draw examples of primary through quaternary protein structure
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 or all 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 typewritten report or informal report sheet, typically completed by hand), 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)
- An oral presentation and oral quiz may substitute either a single written experiment report or Final Lab Exam (in whole, or in part), at the discretion of the instructor
Consult the Douglas College Bookstore for the latest required textbooks and materials. Example textbooks and materials include:
Organic Chemistry by D. Klein (current edition)
Chemistry 2421 Laboratory Manual, Douglas College
Carbonless copy paper notebook