Course

Organic Chemistry – Part I

Faculty

Science & Technology

Department

Chemistry

Course Code

CHEM 2321

Credits

5.00

Semester Length

Max Class Size

Method(s) Of Instruction

Lecture

Lab

Typically Offered

Fall

Summer

Overview

Course Description

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.

Course Content

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. S_N2 reactions - mechanism, transition state, stereochemical outcomes, reaction kinetics. S_Nl reactions - mechanism, carbocation stability, stereochemical outcomes, kinetics. Factors affecting rates and outcomes of S_Nl and S_N2 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.

Laboratory Content

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

Learning Activities

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%)

Laboratory (30%)

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)

Note:

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.

Learning Outcomes

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 S_Nl or S_N2 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,

Textbook Materials

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 2321 Laboratory Manual, Douglas College

Safety eyewear

Carbonless copy paper notebook

Lab coat

Requisites

Prerequisites

CHEM 1110

Corequisites

Courses listed here must be completed either prior to or simultaneously with this course:

No corequisite courses

Equivalencies

Courses listed here are equivalent to this course and cannot be taken for further credit:

No equivalency courses

Course Guidelines

Course Guidelines for previous years are viewable by selecting the version desired. If you took this course and do not see a listing for the starting semester / year of the course, consider the previous version as the applicable version.

May 2019 (Current)

Course Transfers

These are for current course guidelines only. For a full list of archived courses please see https://www.bctransferguide.ca

Institution	Transfer Details for CHEM 2321
Alexander College (ALEX)	ALEX CHEM 201 (4)
Camosun College (CAMO)	CAMO CHEM 230 (4)
Capilano University (CAPU)	CAPU CHEM 200 (4)
Kwantlen Polytechnic University (KPU)	KPU CHEM 2320 (4)
Langara College (LANG)	LANG CHEM 2316 (4)
Okanagan College (OC)	OC CHEM 212 (3)
Simon Fraser University (SFU)	SFU CHEM 281 (4)
Thompson Rivers University (TRU)	TRU CHEM 2120 (3)
Trinity Western University (TWU)	TWU CHEM 221 (3)
University of British Columbia - Okanagan (UBCO)	UBCO CHEM 203 (3) or UBCO CHEM 213 (3)
University of British Columbia - Vancouver (UBCV)	UBCV CHEM 2nd (4)
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)
University of Northern BC (UNBC)	UNBC CHEM 201 (3) & UNBC CHEM 250 (1)
University of the Fraser Valley (UFV)	UFV CHEM 213 (4)
University of Victoria (UVIC)	UVIC CHEM 231 (1.5)
Vancouver Community College (VCC)	VCC CHEM 2130 (4)
Vancouver Island University (VIU)	VIU CHEM 231 (4)

Course Offerings

Winter 2023

CRN

13087

Mon Wed

Start Date

03-Jan-2023

End Date

13-Apr-2023

Start Date

03-Jan-2023

End Date

13-Apr-2023

Instructor Last Name

Gibson

Instructor First Name

Gregory

Course Status

Waitlist