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 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.
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%)
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:
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
Courses listed here must be completed either prior to or simultaneously with this course:
Courses listed here are equivalent to this course and cannot be taken for further credit:
This course is not required for any other course.
|Institution||Transfer Details||Effective Dates|
|Alexander College (ALEX)||ALEX CHEM 202 (4)||2013/01/01 to -|
|Camosun College (CAMO)||CAMO CHEM 231 (4)||2013/01/01 to -|
|Capilano University (CAPU)||CAPU CHEM 201 (4)||2004/09/01 to -|
|Kwantlen Polytechnic University (KPU)||KPU CHEM 2420 (4)||2004/09/01 to -|
|Langara College (LANG)||LANG CHEM 2416 (4)||2004/09/01 to -|
|Okanagan College (OC)||OC CHEM 222 (3)||2005/09/01 to -|
|Simon Fraser University (SFU)||SFU CHEM 282 (2), Q & SFU CHEM 286 (2) - Q & SFU CHEM 1XX (1)||2004/09/01 to 2011/12/31|
|Simon Fraser University (SFU)||SFU CHEM 283 (3), Q & SFU CHEM 286 (2) - Q||2012/01/01 to -|
|Thompson Rivers University (TRU)||TRU CHEM 241 (3) & TRU CHEM 246 (1), OL||2004/09/01 to 2010/12/31|
|Thompson Rivers University (TRU)||TRU CHEM 2XXX (3)||2010/09/01 to 2015/04/30|
|Thompson Rivers University (TRU)||TRU CHEM 2220 (3)||2015/05/01 to -|
|Thompson Rivers University (TRU)||TRU CHEM 2223 (3) & TRU CHEM 2225 (1), OL||2011/01/01 to 2013/08/31|
|Thompson Rivers University (TRU)||TRU CHEM 2XX (3)||2004/09/01 to 2010/08/31|
|Thompson Rivers University (TRU)||TRU CHEM 2223 (3) & TRU CHEM 2225 (0), *Lab, OL||2013/09/01 to -|
|Trinity Western University (TWU)||TWU CHEM 222 (3)||2004/09/01 to -|
|University of British Columbia - Okanagan (UBCO)||UBCO CHEM 204 (3) or UBCO CHEM 214 (3)||2004/09/01 to -|
|University of British Columbia - Vancouver (UBCV)||DOUG CHEM 2321 (5) & DOUG CHEM 2421 (5) = UBCV CHEM 203 (4) & UBCV CHEM 213 (3) & UBCV CHEM 245 (1)||2004/09/01 to -|
|University of British Columbia - Vancouver (UBCV)||UBCV CHEM 2nd (4); DOUG CHEM 2321 (5) & DOUG CHEM 2421 (5) = UBCV CHEM 203 (4) & UBCV CHEM 213 (3) & UBCV CHEM 245 (1)||2004/09/01 to -|
|University of Northern BC (UNBC)||UNBC CHEM 203 (3) & UNBC CHEM 251 (1)||2004/09/01 to -|
|University of the Fraser Valley (UFV)||UFV CHEM 214 (4)||2004/09/01 to -|
|University of Victoria (UVIC)||UVIC CHEM 232 (1.5)||2004/09/01 to 2019/04/30|
|University of Victoria (UVIC)||UVIC CHEM 234 (1.5)||2019/05/01 to -|
|University of Victoria (UVIC)||UVIC CHEM 232 (1.5)||2004/09/01 to -|
|Vancouver Community College (VCC)||VCC CHEM 2230 (4)||2019/05/01 to -|
|Vancouver Island University (VIU)||VIU CHEM 232 (4)||2004/09/01 to -|