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1 CHEM 261 (AS 41) Organic Chemistry I Fall 2016 Instructor: Dr.ManzarSaberi Office: 5- 138 G, City Center Campus Phone: (780) 497-4634 Email: [email protected] Lectures: Tuesday, Thursday12:30-1:50 CCC Room 5-301 Office Hours: Monday, Wednesday, Friday10:00-11:00, and Thursday 11:00-12:00. Total Course Hours: Lecture 45 hours, Laboratory 36 hours Web address:http://academic.macewan.ca/saberim Textbook: Organic Chemistry by T. W. Graham Solomons, Craig B. Fryhle, and Scott A. Synder12th edition Laboratory Manual: Organic Chemistry 261 Laboratory Manual edition 2016 Optional Materials: Study Guide and Solution manual and molecular model kit. Grade Distribution: Term I Exam- Thursday, October 6 (80 min) 22.5 % Term II Exam- Thursday, November 3(80 min) 22.5 % Final Examination (3.0 Hours) 30 % Laboratory Component 25% Laboratory Examination,Thursday December 1, 6:00-7:30 PM Note: Students are responsible for verifying the date of the final exam (see here). Course Description:(3 credits) This course studies the molecular structure and reactivity of organic compounds based on their functional groups and is intended for students who have obtained at least three credits in Introductory University Chemistry. The course provides an introduction to nomenclature, three dimensional structure and physical properties of organic compounds as well as reaction mechanisms and infrared spectroscopy. Although most organic functional groups are discussed, the focus is on the chemistry of alkanes, alkenes, alkynes and alkyl halides. Mechanisms of nucleophilic substitution and elimination reactions of alkyl halides are discussed. Note: Credit can only be obtained in one of CHEM 161 or CHEM 164 or CHEM 261. Prerequisite: A minimum grade of C- in CHEM 101 or in CHME 103, or greater than 90% in Chemistry 30 Upon completion of this course, the student will be able to: • Apply chemical concepts learned in the lecture to laboratory situations and vice versa. • Represent the structure and geometry of organic molecules using basic bondingtheories (Lewis Theory, Valence Bond Theory andMolecular Orbital Theory). • Identify organic functional groups and name simple organic compounds. • Identify the presence of certain functional groups within molecules using infraredspectroscopy. • Apply chemical kinetics and thermodynamics to the study of organic reactions. • Identify the presence of certain functional groups within molecules using infraredspectrocopy. • Apply chemical kinetics and thermodynamics to the study of organic reactions (freeenergy diagrams, transition states, reactive intermediates and mechanisms). • Represent the different possible conformations of simple alkanes and cycloalkanes. • Identify chiral compounds and explain chirality and optical activity. • Identify and represent constitutional isomersim and stereoisomerism in organiccompounds. • Summarize the reactivity of a number of functional group classes (alkanes andcycloalkanes, alkyl halides, alkenes and alkynes). • Represent different reaction mechanisms of alkyl halides (Sn1/E1 and Sn2/E2) andidentify the factors that determine which reaction occurs. Laboratory: Laboratory classes begin the second week of the term. The laboratory component is compulsory for credit in CHEM 261; attendance is mandatory and no make-up labs are available. If you know that you will be unable to attend a scheduled laboratory period, it is yourresponsibility to inform your laboratory instructor at least one week prior so that you can complete the experiment in another laboratory session. If a laboratory period is missed for a valid reason, the experiment may not be counted towards the final laboratory grade. In all other cases, a mark of zero will be assigned. To obtain a minimum grade of C- in CHEM 261, a score of 50% or higher must be obtained for the laboratory component and, at least 70% of the experiments, must be completed 2 Grading:MacEwan University adheres to the Alberta Common Grading Scheme, which is a 12 point letter grade system. While faculty may use percentages to aid in their grade development, only the letter grade will appear on transcripts. A+ 95 - 100% 90 – 94% A A- B+ Excellent 85 – 89% 80 – 84% B 75 – 79% B- 70 – 74% C+ Good 65 – 69% C 60 - 64% C- 55 – 59% D+ 50 - 54% D 45 - 49% F below 45% Satisfactory Minimum Pass Fail Official grades will be provided by the Office of the University Registrar through myStudentSystem. A minimum grade of C– is required to receive transfer credit or to satisfy a prerequisite for a higher level course. Important Dates: Sept 7 Sept 12 Sept 16 Oct 10 Nov 9-10 Dec 5 Dec 5 Dec 7-16 First day of classes Laboratories begin Last day for program changes (drop/add courses) Thanksgiving (no classes - University closed) Reading week (no classes or laboratories) Last day of classes Last day to withdraw from courses (without academic penalty) Final examination period Student Responsibilities: Students are expected to be aware of their academic responsibilities as outlined in MacEwan University Policy E3101: Student Rights and Responsibilities (found here). 1. Academic Integrity: All forms of student dishonesty are considered unacceptable. MacEwan University Policy C1000: Academic Integrity (found here) promotes honesty, fairness, respect, trust, and responsibility in all academic work. According to the policy, “Academic dishonesty involves participating in acts by which a person fraudulently gains or intentionally attempts to gain an unfair academic advantage thereby compromising the integrity of the academic process”. All incidents of academic dishonesty are reported and recorded by the Academic Integrity Office. The penalties and sanctions for academic dishonesty can include the following: a mark reduction up to zero on a piece of academic work, a grade reduction up to an F in the course, and suspension or expulsion (with transcript notation) from the University. Please see the academic integrity policy for more details. You are responsible for understanding what constitutes academic dishonesty. 2. Registration Status: You are responsible for your registration status at the University. Academic advisors (Rm 6-211) may assist you with the process of registration, including adding or dropping of courses, but it is your responsibility to verify that these changes have been officially completed. This verification can be done at any time using myStudentSystem. You should check your official registration status before the last date to officially withdraw from the course. 3. Course prerequisites: Students are responsible for having all prerequisites required for a given course. Prerequisite checks are periodically carried out and any students who do not have the appropriate prerequisite may be removed from the course. If you are removed from the course, you may be responsible for any tuition costs up to the date of removal. Any courses from another post-secondary institute cannot be used as a prerequisite until assessed and approved for transfer credit. 4. Withdrawing From The Course: If you stop attending class you must complete a Course Drop Form, have it signed by a Academic Advisor (Rm 6-211), and submit it to the Office of the University Registrar by the last day to withdraw as provided in the Academic Schedule in the Academic Calendar. Failure to officially withdraw will result in a grade being assigned based on course work completed. Late withdrawals are only allowed in exceptional circumstances. 5. Exams: Your student photo I.D. is required at exams. It is at the discretion of the instructor whether you will be allowed to write the exam if you arrive over 15 minutes after the exam has begun. You must remain in the exam room for at least 20 minutes from the time it commenced. Only calculators approved for use by the instructor may be used during examinations, which include any laboratory and lecture quizzes. Any devices capable of external communication, such as cell phones, iPods and blue tooth enabled devices, cannot be used for exams of any type. Permission to use the washroom during exams is at the discretion of the instructor and may require accompaniment. 6. Missed Term Exams: If you miss a term examination you must provide the instructor with an explanation within 24 hours or a mark of zero may be given. Notification may be provided through email, voice mail, or direct contact with the instructor. Official documentation as to why the examination was missed will be needed to assess whether your absence will be excused or not. If 3 your absence is excused the weight of this examination will be added to the weight of the final examination in the course. Medical excuses must include the date you were examined, the specific dates for the period of the illness, a clear statement indicating that the severity of the illness prevented you from attending school or work, and the signature of the examining physician (a signature by office staff on behalf of the physician is not acceptable). Medical notes obtained subsequent to the date of the examination are generally not accepted. A mark of zero will be given if the instructor considers the excuse inappropriate or inadequately substantiated. 7. Final Exams: You are responsible for accessing and confirming the official date, time, duration and location of the final exam. The Office of the University Registrar releases the official schedule no later than half-way through the term. This schedule is available here . Students are required to be available for the entire exam period. For further information, see MacEwan University Policy C2005: Final Assessment (found here). 8. Deferred Final Exam: University policy allows for the deferral of exams for extenuating circumstances, such as illness or catastrophic events. To apply for a deferral, see Program Services (Rm 6-211). Applications must be received by Program Services within two business days of the missed exam. A fee of $50 per exam, up to a maximum of $100, will be charged to your account. Note that a vacation, even if paid for and/or documented, is not grounds for an exam deferral. Application forms are available from the Program Services office, and must be submitted with appropriate documentation. Students should advise their instructor prior to the examination if they know beforehand that they will be unable to attend the scheduled examination time. If you have any questions about the process please contact Program Services (780 497 4520 or [email protected]). For further information please refer to MacEwan University Policy C2005: Final Assessment (found here) and Policy C2020: Grading (found here). 9. Late Assignments (including laboratory assignments): As due dates for assignments are known well in advance, medical and other excuses are generally not accepted as a reason for submitting late assignments. 10. Cell Phones: All cell phones are to be turned off during class and exam periods (except under exceptional circumstances in which approval has been given by the instructor). 11. Students with Disabilities: Students with disabilities who may have special requirements in this course are advised to discuss their needs with Services to Students with Disabilities located in the Student Life office. You should advise the course instructor(s) of any special needs that are identified. See Policy E3400 Students with Disabilities (found here). 12. Student Appeals: The University has a policy regarding Student Appeals (E3103, found here). You should access this policy to become aware of the deadlines and guidelines that need to be followed if you are appealing a grade or other University assessment. Assistance with the appeals process is available through counsellors in the Student Life office. Please call 780 497 5064 to make an appointment. 13. MyMacEwan.ca Email: All students are given a <name>@mymacewan.ca email address. This email address is available to the course instructor who may distribute relevant course information or announcements via email. The Faculty of Arts and Science regularly communicate with students via email. Check your mymacewan.ca email regularly or forward it to an email address you check regularly. If you use email to communicate with your instructor, you must use your mymacewan.ca account. This is to protect your privacy; if a non-mymacewan.ca account is used, there is no way for an instructor to verify the identity of the sender. Disclaimer: The information in this course outline is subject to change. Any changes will be announced in class or, if applicable, in the laboratory. Chem261 Chapter 1: The Basics: Bonding and Molecular Structure Atomic Structure - Isotopes - Valence Electrons Chemical Bonds: The Octet Rule - Ionic bond - Covalent bond How to write Lewis Structures Formal Charges and How to Calculate Them Isomers: Different Compounds That Have the Same Molecular Formula How to write and Interpret Structural Formula - Dash Structural Formulas - Condensed Structural Formulas 4 - Bond-Line Formulas - How to Draw Bond-Line Formulas - Three-Dimensional Formulas Resonance Theory - The Use of Curve Arrows - How to Write Resonance Structures - Rules For Writing Resonance Structures - How To Decide When One Resonance Structure Contribute More To The Hybrid Than Another Atomic Orbitals and Electron Configuration Molecular Orbitals The Structure of Methane and Ethane: sp3 Hybridization The Structure of Ethene (Ethylene): sp2 Hybridization - Restricted Rotation and the Double Bond - Cis-Trans Isomerism The Structure of Ethyne (Acetylene): sp Hybridization How to Predict Molecular Geometry: The Valence Shell Electron Pair Repulsion Model - Methane - Ammonia - Water - Boron Trifluoride - Beryllium Hydride - Carbon Dioxide Text Sections: 1.2-1.17 Chapter 2: Families of Carbon Compounds: Functional Groups, Intermolecular Forces, and Infrared (IR) Spectroscopy Hydrocarbons: Representative Alkanes, Alkenes, Alkynes, and Aromatic Compounds - alkanes - alkenes - alkynes - benzene: A representative Aromatic hydrocarbon Polar Covalent Bonds Polar and Nonpolar Molecules Dipole Moments in Alkenes Functional Groups - alkyl groups and the symbol R - phenyl and benzyl groups - alkyl halides or haloalkanes - alcohols and Phenols - ethers - amines - aldehydes and ketones - carboxylic acids esters amides - nitriles Summary of Important Families of Organic Compounds Physical Properties and Molecular Structures - Ionic Compounds: ion-ion forces Intermolecular Forces (Van der Waals Forces) - dipole –dipole forces - hydrogen bonds - Dispersion Forces Dipole-Dipole Forces Boiling Points 5 Solubilities Guidelines for Water Solubility Summary of Attractive Electronic Forces Infrared Spectroscopy: An Instrumental Method for Detecting Functional Groups Interpreting IR Spectra Infrared Spectra of Hydrocarbons IR Spectra of Some Functional Groups Containing Heteroatoms How to Interpret an IR Spectrum without Any Knowledge of the Structure Applications of Basic Principles How to Gain Structural Information from Molecular Formulas and the Index of Hydrogen Deficiency Text Sections:2.1-2.17, 4.17 Chapter 3: An Introduction to Organic Reactions and Their Mechanism: Acids and Bases Acid-Base Reactions - the Bronsted-Lowry Defination of acids and Bases - the lewis Definition of Acids and Bases - opposite charge attract How to Use Curved Arrows in Illustrating Reactions Lewis Acids and Bases Heterolysis of Bonds to Carbon - Carbocations - Carbanions - Electrophiles - Nucleophiles The Strength of Bronsted-Lowry Acids and Bases: Ka and pka - The Acidity Constant, Ka Acidity and pka - Predicting the Strength of Bases How to Predict the Outcome of Acid-Base Reactions Relationship between Structure and Acidity - The Effect of Hybridization - Inductive Effect Acidity: Carboxylic Acids versus Alcohols - The effect of Delocalization - The Inductive Effect - Summary and a Comparison of Conjugate Acid-Base Strength - Inductive Effect of Other Groups - Strength of Phenols and Acids - Distinguishing and Separating Phenols from Alcohols and Carboxylic Acids The Effect of Solvents on Acidity Organic Compounds as Bases A mechanism for an Organic Reaction Acids and Bases in Non-aqueous Solution Acid and Bases and the Synthesis of Deuterium and Tritium-Labeled Compounds Text Sections: 3.1-3.7, 3.10-3.15. Chapter 4: Nomenclature and Conformations of Alkanes and Cycoalkanes Introduction to alkanes and Cycloalkane Shape of Alkanes How to name Alkanes, Alkyl Halides, and Alcohols: The IUPAC System - nomenclature of unbranched alkyl groups - nomenclature of branched-chain alkanes - nomenclature of branched alkyl groups - classification of hydrogen atoms - nomenclature of alkyl halides 6 - nomenclature of alcohols How to Name Cycloalkanes - monocyclic compounds - bicyclic compounds How to Name Alkenes and Cycloalkenes How to Name Alkynes Physical Properties of Alkanes and Cycloalkanes Sigma Bonds and Bond Rotation Newman Projections and How to Draw Them How to do Conformational Analysis Conformational Analysis of Butane Stereoisomers and Conformational Stereoisomers The relative Stabilities of Cycloalkanes: Ring Strain - cyclopropane - cycobutane - cyclopentane Conformations of Cyclohexane: The chair and the boat Conformations of Higher Cycloalkanes Substituted Cyclohexanes: Axial and Equatorial Hydrogen Groups How to Draw Chair Conformational Structures A Conformational Analysis of Methylcyclohexane 1,3-Diaxial interactions of a tert-Butyl Group Disubstituted Cycloalkanes: Cis – trans Isomerism Cis –Trans isomerism and Conformational Structures of Cyclohexanes Bicyclic and Polycyclic Alkanes Chemical Reactions of Alkanes Synthesis of Alkanes and Cycloalkanes Hydrogenation of alkenes and alkynes How to Gain Structural Information from Molecular Formulas and the Index of Hydrogen Deficiency Text Sections: 4.1-4.17. Chapter 5: Stereochemistry: Chiral Molecules Chirality and Stereochemistry Isomerism: Constitutional Isomers and Stereoisomers Enantiomers and Chiral Molecules Molecules having one Chirality Center are Chiral Tetrahedral versus Trigonal Stereogenic Center How to test for Chirality: Planes of symmetry Naming Enantiomers: The R, S –System How to Assign (R) and (S) Configurations Properties of Enantiomers: Optical Activity - specific rotation - Plane polarized light - The polarimeter Racemic forms - Racemic forms and Enantiomeric Excess The Synthesis of Chiral Molecules - racemic Mixtures Molecules with More than One Chirality Center - How to Draw Stereoisomers for Molecules having more than one Chirality Center - Meso compounds - How to name Compounds with more than one Chirality Center Fischer Projection Formulas How to Draw and Use Fischer Projections Stereoisomerism of Cyclic Compounds 7 - Cyclohexane Derivatives Relating Configurations through Reactions in which No Bonds to the Stereogenic Carbon are broken Relative and Absolute Configurations Separation of Enantiomers: Resolution Text Sections: 5.1- 5.4, 5.6-5.10, 5-12 –5-17. Chapter 6: Nucleophilic Substitutions: Properties and Substitution Reactions of Alkyl Halides and Alkyl Halides Nucleophilic Substitution Reactions Nucleophiles Leaving Groups Kinetics of a Nucleophilic Substitution Reaction: An SN2 Reaction - How do we Measure the Rate of This Reaction? - What is the Order of This Reaction? A Mechanism for SN2 Reaction The Stereochemistry of SN2 Reactions The Reaction of Tert-Butyl Chloride with Water A Mechanism for the SN1 Reaction Carbocations - The Structure of Carbocations - The Relative Stabilities of Carbocations The Stereochemistry of SN1 Reactions - Reactions that Involve Racemization - Solvolysis Factor Affecting the Rate of SN1 and SN2 Reactions - The Effect of the Structure of the Substrate - The Effect of the Concentration and Strength of the Nucleophile - Solvent Effects in SN2 and SN1 Reactions - The Nature of the Leaving Group Organic Synthesis: Functional Group Transformations Using SN2 Reactions Text Sections: 6.1- 6.6, 6.8-6-14. Chapter 7: Alkenes and Alkynes: Properties and Synthesis. Elimination Reactions of Alkyl Halides Introduction PHYSICAL Properties of Alkenes and Alkynes The (E) – (Z) System for Designating Alkene Diastereomers How to Use the (E) –(Z) System Relative Stabilities of Alkenes - heat of reaction - overall relative stabilities of alkenes Cycloalkenes Synthesis of Alkenes: Elimination Reactions Dehydrohalogenation of Alkyl Halides - Bases Used in Dehydrohalogenation - Mechanism of Dehydrohalogenation The E2 Reaction - Zaitsev’s Rule: Formation of the more Substituted Alkene is Favored with a Small Bases - Formation of the Less Substituted Alkenes Using a Bulky Base - The Stereochemistry of E2 Reactions: The Orientation of Group in the Transition State How to Favor an E2 Mechanism Elimination and Substitution Reactions Compete with Each Other How to Determine Substitution or Elimination is Favored Elimination of Alcohols: Acid-Catalyzed Dehydration - Mechanism for Dehydration of Secondary and Tertiary Alcohols: An E1 Reaction - Carbocation Stability and Transition State 8 Carbocation Stability and Occurrence of Molecular Rearrangements - Rearrangements During Dehydration of Secondary Alcohols - Rearrangement After Dehydration of a Primary Alcohol The Acidity of Terminal Alkynes Synthesis of Alkynes by Elimination Reactions Practical Considerations for Alkyne Synthesis by Double Dehyrohalogenation The Terminal Alkynes Can be converted to Nucleophiles for Carbon-Carbon Bond Formation General Principle of Structure and Reactivity Illustrated by the Alkylation of Alkynide Anion Text Sections: 7.1- 7-7, 7.9-7.10(a-b), 7.11-7.14 T.W.GrahamSolomons , Craig B. Fryhle and Scott A. Snyder Organic Chemistry, 12th edition Learning and studying guide 1. Read the text before class. Don’t expect to understand it, just read it. When reading novels, plays, or poetry in English, do you read the text before or after the class discussion? In which would you participate more and learn more in the process? Studies have shown that individuals remember about 10 % of material the first time they are introduced to it and up to 50 % the second time. By reading the textbook before class, you acquaint yourself with the information so that the classroom is where you see the material for the second time. You will find yourself saying, “Oh, so that’s what the textbook means!” Studies also show that reviewing your notes within 24 hours of taking them also improves retention. 2. Rewrite your notes at midterm and again at the end of term. Writing is a form of active learning. Rewriting your notes forces you to critically review the information, follow the ‘train-of-thought’ of the instructor, and say it in your own words. Importantly, you end up with a smaller set of notes from which to study for the final! Cue cards are great study tool and convenient when traveling. 3. When studying, don’t just read, write! Rewrite your notes, solve problems, and redo derivations. Prepare a ‘super-summary’ of your notes that contains only the important concepts. When you review the summary, fill in the details in your mind. 4. Don’t pull ‘all nighters’. Your ability to lean when fatigued is very low. Furthermore, your minds’ ability to recall information and dynamically formulate answers is faster if you get a good nights’ sleep rather than if you live off caffeine, etc. 5. Don’t study right up to the exam. Take at least a four-hour break before the exam. Get active: go for a walk, to the gym, etc. Your mind can better consolidate what you have learned if you aren’t cramming more in. Your mind will be refreshed for the exam and you will be able to recall information faster. Exam-taking suggestions 1. Read the exam start to finish. This should take no more than a few minutes but will give you an overview of the entire exam. Your mind will begin processing all the questions. Some instructors even give hints/answers to questions in other questions. How many times have you been stumped on a question during the exam and, while walking away, had a revelation on how to answer it. You weren’t thinking about it, were you? Now consider if your mind had been unconsciously processing that question for a while longer (like from the start of the exam). 2. Go through the exam and answer questions you know ‘by heart’.