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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
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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
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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
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- 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
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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
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- 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
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- 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
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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’.