COURSE OUTLINE. School of Engineering Technology and Applied Science. Applied Biological and Environmental Science (ABES)

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1 COURSE OUTLINE SCHOOL: School of Engineering Technology and Applied Science DEPARTMENT: Applied Biological and Environmental Science (ABES) PROGRAM: COURSE TITLE: Biological Technician/Technologist, Environmental Protection Technician /Technologist Organic Chemistry COURSE CODE: CH 121 TOTAL COURSE HOURS: 75 PRE-REQUISITES/CO-REQUISITES: CH 101 COURSE ELIGIBILITY FOR PRIOR LEARNING ASSESSMENT AND RECOGNITION (PLAR): Yes ORIGINATED BY: Hillary Dzikowski REVISED BY: Smilja Jankovic DATE: August 2009 APPROVED BY: Academic Year: Chairperson/Dean Please Note: It is the responsibility of students to retain all course outlines for the purpose of applying for transfer of credit to other educational institutions. A fee may be charged for further copies. 8/19/2009 THIS COURSE ADHERES TO ALL COLLEGE POLICIES (See College Calendar) Page 1

2 COURSE DESCRIPTION: This course is an introduction to the theoretical and practical application of organic chemistry. It is designed to introduce students to the principles of structure, properties identification and reactions of organic compounds as related to the various areas of science (biological and other) and life in general. This course is a combination of theory and hands on lab. COURSE LEARNING OUTCOMES: Upon successful completion, students will be able to: 1. Draw structural, condensed and molecular formulas for straight chain and ring chain hydrocarbons and their derivatives 2. Name these hydrocarbons and their derivatives using their common names, trivial names as well as IUPAC method of nomenclature 3. Identify and interpret physical and chemical characteristics of these hydrocarbons and their derivatives 4. Demonstrate proficiency in laboratory techniques related to preparation, separation, purification and identification of organic compounds 5. Document experimental data in a variety of reports as outlined in the laboratory manual 6. Interpret and validate experimental data to develop appropriate conclusions ESSENTIAL EMPLOYABILITY SKILLS (EES): This course supports the students ability to: communicate clearly, concisely and correctly in the written, spoken, and visual form that fulfills the purpose and meets the needs of the audience. execute mathematical operations accurately. apply a systematic approach to solve problems. use a variety of thinking skills to anticipate and solve problems. PRIOR LEARNING ASSESSMENT & RECOGNITION PROCESS (es) This course is eligible for PLAR through the Registrar and SETAS offices. Assessment of portfolio and/or testing may be discussed with faculty. EVALUATION & GRADING SYSTEM: Theory: Test % Test % Test % Laboratory: 30.0% Students must pass both theory and lab components of this course, separately, in order to be successful. Each lab report is due one week after the experiment has been completed. Two marks per week per late report will be deducted for each late Lab. Report STUDENT ACCOMMODATION: All students have the right to study in an environment that is free from discrimination and/or harassment. It is College Policy to provide accommodation based on grounds defined in the Ontario Human Rights Code. Accommodation may include changes or modifications to standard practices. Students with disabilities who require academic accommodations must register with the Centre for Student with Disabilities. Please see the Centre for Students with Disabilities for details. 8/19/2009 THIS COURSE ADHERES TO ALL COLLEGE POLICIES (See College Calendar) Page 2

3 Students requiring accommodation based on human rights grounds should talk with their professors as early as possible. Details are available on the Centennial College website ( ). If students are unable to write an examination due to a medical problem or unforeseen family problems, they should immediately contact their professor or program Chair for advice. In exceptional and well documented circumstances (e.g. unexpected family problems, serious illness, or death of a close family member), students should be able to write a make-up examination to replace an examination missed. TEXT AND OTHER INSTRUCTIONAL/LEARNING MATERIALS: A plastic wrapped textbook package containing two (2) books: Text: Mifflin. "A Short course in Organic Chemistry" by Hart, Craine & Hart, 12th edition, published by Houghton Laboratory: "Organic Experiments" by Linstromberg and Baumgarten, 6th edition USE OF DICTIONARIES: Dictionaries may not be used during test or exam time. 8/19/2009 THIS COURSE ADHERES TO ALL COLLEGE POLICIES (See College Calendar) Page 3

4 College Policies POLICY STATEMENTS The following statements are selected from Centennial College policies approved by the Board of Governors. Student Responsibilities Students are expected to know the contents of the course outline and to discuss with the professor any areas where clarification is required. Students should keep all course outlines for each course taken at Centennial College. These may be used to apply for transfer of credit to other educational institutions. A fee may be charged for additional or replacement copies. Other Policies Students should familiarize themselves with all College Policies that cover students rights, responsibilities, and the Academic Appeal process. For further information, consult the Academic Matters Section in the full-time and Continuing Education calendars. The Academic Appeal Application form is available from any Enrolment Services Office. Proof of Student Status Students must produce official photo identification at any time during the semester when requested to do so by any professor. (The official piece is the Centennial Student Card.) Continuing Education students do not have Centennial Student Cards, and so they may use other forms of photo identification, such as a driver s license, health card, or other government-issued photo identification. Final Examinations When writing a test or examination, students must put their official photo-id cards in full view for review by the invigilator. Students who do not have official photo-id will be permitted to write the examination with a substitute photo-id, but they will be required to produce photo-id at the program or department office within 24 hours or the next business day following the examination, or else the examination results will be void. More Final Examination Policies are available at Academic Progression Policy for Diploma and Certificate Programs: College Academic Standings will be applied. Calendar. Please see Academic Policies and Procedures, Full-Time Faculty Consultation Professors are available to see students outside of class time. Students can contact professors via voice mail, , or through their program or department office. Information regarding how to contact teachers will be provided at the beginning of the course and is also available in the program or department office. Human Rights Statement It is the policy of the College that all programs will strive for a learning, teaching, and working environment that promotes inclusion, understanding, and respect for all students and employees, consistent with the Ontario Human Rights Code and Centennial College's Statement of Diversity. 8/19/2009 THIS COURSE ADHERES TO ALL COLLEGE POLICIES (See College Calendar) Page 4

5 TOPICAL OUTLINE Topic Topic/Content Readings Instructional Objectives Instructional Strategies/ Tests and Assignments History of Organic Chemistry. Organic chemistry in every day life. Families of organic compounds. Chapter 1 Carbon & the Covalent Bond. Chapter 1 Aliphatic Hydrocarbons. Saturated/unsaturated. Classification according to functional groups. Alkanes, alkenes & alkynes. Nomenclature. International system. IUPAC (rules) Common & trivial names. Physical properties: Solubility. Hydrogen bonding. Flammability. boding point. Isomerism: Positional isomers. Functional group isomers. Geometric isomers. Chemical reactions of aliphatic series of hydrocarbons. Oxidation reaction. Addition reaction. Elimination reaction. Chapter 1 Chapter 2 Chapter 2 Page 58 Chapter 3 Page 71 Define organic chemistry & supply specific examples of its' application to every day life. Distinguish between aliphatic, cyclic and aromatic compounds. Account for the tetravalancy of carbon atom from its electronic structure. Identify polar & nonpolar bonds with reference to the hydrogen bond. Draw electron-dot structures of carbon compounds. Define basic terms used in organic chemistry. Write structures for the functional groups and classify families of organic compounds. Recognize structural, condensed & molecular formulas of continuous chain hydrocarbons. Given the structural formula of an alkane, alkene & alkyne, name them according to the IUPAC. Draw structural formulae for alkanes, cycloalkanes, alkenes and alkynes given their I.U.P.A.C. names. Explain why alkanes are insoluble in water, why alkanes & alkenes have lower densities than water. Why alkanes have lower boiling points for a given molecular weight than most organic compounds. Define isomers. Distinguish between chain & positional isomers with appropriate examples. Identify Cis & Trans geometric isomers. Write structural formulas for & name each of the isomeric pentanes by the IUPAC system. Distinguish between addition & elimination reactions of aliphatic hydrocarbons. Write equations for laboratory methods for preparing, an alkane, an alkene & an alkyne, starting with four carbon or fewer carbon atoms and any solvent or inorganic reagent. Describe a useful, simple lab test for distinguishing between saturated & unsaturated compounds. Predict the products of combustion, halogenation substitution, addition & elimination reactions of saturated or unsaturated hydrocarbons. State & illustrate Markovnikov's rule by way of examples. 8/19/2009 THIS COURSE ADHERES TO ALL COLLEGE POLICIES (See College Calendar) Page 5

6 Topic Topic/Content Readings Instructional Objectives Instructional Strategies/ Tests and Assignments Substitution reaction. 8 Arenes: Aromatic Hydrocarbons Orbital model of benzene. Mono and disubstituted benzenes. Nomenclature. Chapter 4 Page 116 Describe the aromatic characteristics of benzene. Draw & explain Kekule's two structures for benzene to illustrate resonance qualities. 9 Reactions of benzene: Electrophilc substitution. Ring activating groups. Ring deactivating groups. Para, meta, ortho, directing groups. Use of catalyst in these reactions. Chapter 4 Contrast an addition reaction of an alkene to a substitution reaction of benzene. Write & name structured formulas for simple mono derivatives of benzene with specific reagents. Indicate the main mono-substitution products when benzenes are halogenated, nitrated, sulfonated or hydrogenated. Identify whether substituents on the benzene ring are ortho or para directing and whether they are ring activating or deactivating. Predict products formed when these compounds are reacted with common reagents. 9.1 Organic Halogen Compounds 10 Classification and tests for Alcohols. Nomenclature Physical properties and Hydrogen bonding in alcohols & phenols. Chemical reactions of alcohols & phenols. Oxidation. Dehydration. Chapter 6 Page 180 Chapter 7 Page 203 Classify Organic Halogen Compounds as primary, secondary, or tertiary. Name and draw structures for a variety of useful halogen compounds like insecticides, solvents, etc. Write equations for nucleophilic substitution reactions of the organic halogen compounds. Define Dehydrohalogenation and show how elimination reactions occur to produce unsaturated hydrocarbons. Classify alcohols in accordance to the carbon to which the OH group is bonded. Label alcohols as primary, secondary or tertiary and show how the Lucas test distinguishes between them. Name alcohols using common names or systematic names. Draw structural formulae from the names of alcohols. Explain the behaviour of alcohols & phenols as weak acids. Draw structures for phenol & glycerol. Write reaction equations for: a) Dehydration of alcohols with strong acids. b) Phenol & sodium hydroxide. c) Oxidation of primary & secondary alcohol to aldehydes & ketones respectively. d) Bromination and nitration of phenol. f) Other reactions selected from the text 8/19/2009 THIS COURSE ADHERES TO ALL COLLEGE POLICIES (See College Calendar) Page 6

7 Topic Topic/Content Readings Instructional Objectives Instructional Strategies/ Tests and Assignments 11 Ethers: Preparation. Nomenclature. Physical features. Chemical reactions. Chapter 8 Page 231 Write equations to show how a given list of ethers can be prepared by dehydration with strong acid or by Williamson synthesis. Assign both common name & IUPAC names for a given list of ethers. Explain why ethers do not exhibit hydrogen bonding Aldehydes & ketones. Aliphatic and Aromatic. Nomenclature. Common names. IUPAC names Physical properties. Boiling point. Stability. Melting point Chapter 9 Page 250 Page 251 Describe the chemical characteristics of carbonyl functional group. Distinguish between aliphatic & aromatic aldehydes and ketones. Using both common & IUPAC names, name & write structural formulae for the commonly used aldehydes & ketones. Name & write structural formulas for aromatic aldehydes & ketones. From a given list of organic compounds classify them as aldehydes, or ketones. Explain why aldehydes and ketones have lower boiling points than alcohols or other hydrogen-containing compounds Simple tests for Aldehydes & Ketones: Benedict's test. Tollen's test. Fehling test. Preparation of aldehyde & ketones. Oxidation of alcohol. Reduction of carboxyl acids. Hydration of alkynes. Tautomers. Keto form. Enol form. Addition reaction of aldehydes & ketones. Formation of hemiacetal & acetal. - of cyanohydrin. - addition of nitrogen nucleophiles. Page 270 Page 257 Differentiate between aldehydes and ketones. Write equations for their reactions, including the oxidation of primary and secondary alcohols as preparation methods. Write equations for the oxidation of alcohols Write equation using Friedel-Craft acylation reaction for the preparation of methyl ketones. Define "Tautomers" giving examples. Draw structural formulas of keto/enol if they exist from a list of paired organic compounds. Write equations for the addition reactions of aldehydes and ketones. Name addition-products of the above reaction. Write equation for the addition of water to aldehydes & ketones to form cyanohydrins. 8/19/2009 THIS COURSE ADHERES TO ALL COLLEGE POLICIES (See College Calendar) Page 7

8 Topic Topic/Content Readings Instructional Objectives Instructional Strategies/ Tests and Assignments - reduction to alcohols. - oxidation to carboxylic acids. - Aldol condensation Write equations for the addition of ammonia & ammonia compounds to aldehydes & ketones Carboxylic Acids & their derivatives: Carboxylate ion. Benzoic acid. Nomenclature of monocarboxylic acids. Dicarboxylic acid and derivatives of benzoic acids. Physical properties for Carboxylic acids Preparation of carboxylic acids: Oxidation product. Side Chain oxidation product. Carbonation of Grignard reagent Chapter 10 Page 283 Page 283 Page 287 Write equation & name the addition product of the reaction of two aldehydes or two ketones. Define and describe the chemical properties of the carboxyl group. Distinguish between mono and di carboxylic acids as well as aromatic carboxylic acids. Describe the structure of fatty acids, hydroxy acids and amino acids with examples. Provide names and structural formulae for the first main carboxylic acids and their salts (common and I.U.P.A.C.) Explain why carboxylic acids have relatively higher BP, MP and water solubilities than aldehydes, ketones and alcohols having corresponding number of carbon atoms. Identify the acidity of carboxylic acids with reference to acid salts and food additives. Identify polyfunctional carboxylic acids and the biological functions of lactic acid and pyruvic acid and salicylic acid. Prepare aliphatic carboxylic acid by oxidation of primary alcohols and aldehydes. Prepare aromatic carboxylic acid by side chain oxidation of methyl substituents on the aromatic ring with potassium permanganate. 23 Basic reactions: Reduction. Salt formation. Page 291 Convert carboxylic acids to salts by treatment with strong base. Reduce carboxylic acids to the corresponding aldehydes by means of catalytic hydrogenation or lithium aluminium hydrides. 24 Carboxylic acid derivatives: Acyl halides.. Esters. Page 296 Prepare acyl halide from acids by reaction with thionyl chloride or phosphorous pentachloride. Prepare acid anhydrides from acids by removing a molecule of water from two carboxylic acids, and connecting the remaining fragments. Preparation of Esters by reaction of an acid with alcohol in the presence of an acid catalyst 8/19/2009 THIS COURSE ADHERES TO ALL COLLEGE POLICIES (See College Calendar) Page 8