ORGANIC CHEMISTRY I
CHM 265- Section: [Insert]
[Insert other course information (optional): blended, honors]
Credit Hours: 5.00
Lab Hours: 4.00
Lecture Hours: 4.00
IAI Core:
IAI Majors: CHM913
Semester: [Insert]
Course Begins: [Insert]
Course Ends: [Insert]
Days: [Insert]
Times: [Insert]
Room: [Insert]
Instructor:
[Insert]
Email: [Insert your @mchenry.edu email address or LMS information]
Phone: [Insert]
Office Hours: [Insert]
Office Location: [Insert]
Other Contact Information: [Insert]
Website (optional): [Insert]
Required Course:
Textbook(s): [Insert]
Supplies (if desired): [Insert]
Course Description:
Organic Chemistry I is the first course in a two-semester sequence of organic chemistry. The course
includes a descriptive study of carbon compounds, including bonding, kinetics and mechanisms of
reactions, aliphatic and aromatic compounds, and reactions of functional groups. Laboratory work
focuses on techniques and handling procedures.
Course Note: Safety goggles are available in the laboratories. Students will be required to complete a
laboratory safety exercise before performing any laboratory experiments.
Course Prerequisite: CHM 166.
Section Notes:
[Insert if applicable]
Course Objectives:
The student will be able to:
Cognitive:
1. Describe the bonding in organic compounds
2. Be able to describe the preparation and chemistry of alkanes, alkenes, alkynes, alcohols and alkyl
halides
3. Use mass spectroscopy, infrared spectroscopy, and nuclear magnetic resonance to determine the
structures of organic compounds
4. Determine the stereochemistry of organic molecules, and be able to describe the stereochemistry
of addition, substitution and free-radical reactions
5. Interpret an energy level diagram of a chemical reaction
6. Use curved arrows to illustrate the mechanism of a chemical reaction
7. Interpret uv-visible spectra.
8.
Appreciative:
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1.
Develop a concern for safety in the chemical laboratory
2. Understand the steps needed to establish the structure of an organic molecule
3. Understand the steps needed to determine the mechanism of an organic reaction
Manipulative:
1. Demonstrate the ability to use simple laboratory apparatus such as electronic balances, burets,
and spectrophotometers
2. Be able to run simple organic reaction
3. Be able to perform organic purification procedures such as extractions, distillations and
recrystallizations
Course Outline:
I. Bonding and Molecular Structure
A. A review of the Valence Bond Theory
B. Formal Charges
C. Resonance Theory
D. Bonding in Methane
E. Bonding in Ethene
F. Bonding in Acetylene
G. Quantum Mechanics and Atomic Structure
H. Drawing Chemical Structures
I. Hybridization of oxygen and nitrogen
J. Laboratory Experiment (0): Safety Precautions, Safety Video, G1, G2, G3
K. Laboratory Experiment (1): Recrystallization, Melting Point, E1
II. Families of Carbon Compounds
A. Hydrocarbons: Representative Alkanes, Alkenes, Alkynes, and Aromatic Compounds
B. Polar Covalent Bonds
C. Functional Groups Family Summary
D. Physical Properties and Molecular Structure
E. Summary of Attractive Electric Forces
F. Infrared Spectroscopy
G. Laboratory Experiment (2): Distillation, E2
III. Introduction to Organic Reactions and Mechanisms
A. Lewis Acids and Bases
B. Carbocations and Carbanions
C. How to Use Curved Arrows in Illustrating Reactions
D. The Strength of Acids and Bases: Ka and pKa
E. Acid-Base Reactions and Relationships between Structure and Acidity
F. Energy Changes, Equilibrium Constant, and the Standard Free-Energy Change, ΔG°
G. The Acidity of Carboxylic Acids
H. The Effect of the Solvent on Acidity
I. Organic Compounds as Bases
J. A Mechanism for an Organic Reaction
K. Acid-Base Reactions and the Synthesis of Deuterium- and Tritium-Labeled Compounds
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L. Laboratory Experiment (3): Thin-Layer Chromatography E3
IV. Nomenclature and Conformations of Alkanes and Cycloalkanes
A. Alkane Isomers and Functional Groups
B. Shapes of Alkanes
C. IUPAC Nomenclature of Alkanes, Alkyl Halides, and Alcohols
D. How to Name Cycloalkanes, Alkenes, Cycloalkenes and Alkynes
E. Physical Properties of Alkanes and Cycloalkanes
F. Conformational Analysis of Alkanes and Cycloalkanes
G. The Relative Stabilities of Cycloalkanes: Ring Strain
H. Conformations of Cyclohexane and Substituted Cyclohexanes
I. Bicyclic and Polycyclic Alkanes
J. Chemical Reactions of Alkanes
K. Synthesis of Alkanes and Cycloalkanes
L. Molecular Formulas and the Index of Hydrogen Deficiency
M. Laboratory Experiment (4): Stereochemistry H473
V. Stereochemistry: Chiral Molecules
A.
B.
C.
D.
E.
F.
G.
H.
I.
J.
K.
L.
M.
N.
O.
P.
Q.
R.
Chirality and Stereochemistry
Isomerism: Constitutional Isomers and Stereoisomers
Enantiomers and Chiral Molecules
Chirality Centers
Biological Importance of Chirality
How to Test for Chirality: Planes of Symmetry
Naming Enantiomers: The R,S-System
Properties of Enantiomers: Optical Activity
The Origin of Optical Activity
The Synthesis of Chiral Molecules and Chiral Drugs
Molecules with More than One Chirality Center
Fischer Projection Formulas
Stereoisomerism of Cyclic Compounds
Relating Configurations through Reactions in Which No Bonds to the Chirality Center Are
Broken
Separation of Enantiomers: Resolution
Compounds with Chirality Centers Other than Carbon
Chiral Molecules that Do Not Possess a Chirality Center
Laboratory Experiment (5): Extraction of Caffeine from Tea E4A
VI. Ionic Reactions: Nucleophilic Substitution and Elimination Reactions of Alkyl Halides
A.
B.
C.
D.
E.
F.
G.
H.
I.
Organic Halides
Nucleophilic Substitution Reactions
Nucleophiles and Leaving Groups
Kinetics, Mechanism and Stereochemistry for the SN2 Reaction
Transition State Theory: Free-Energy Diagrams
The Reaction of tert-Butyl Chloride with Hydroxide Ion: An SN1 Reaction
Kinetics, Mechanism and Stereochemistry for the SN1 Reaction
Carbocations
Factors Affecting the Rates of SN1 and SN2 Reactions
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J.
K.
L.
M.
N.
O.
P.
Organic Synthesis: Functional Group Transformations Using SN2 Reactions
Biological Methylation: A Biological Nucleophilic Substitution Reaction
Elimination Reactions of Alkyl Halides
The E2 Reaction
The E1 Reaction
How to Determine whether Substitutions or Elimination Is Favored
Laboratory Experiment (6): Tests for Alkanes & Alkenes, H472
VII. Alkenes and Alkynes I: Properties and Synthesis. Elimination Reactions of Alkyl
Halides
A.
B.
C.
D.
E.
F.
G.
H.
I.
J.
K.
L.
M.
N.
The (E)-(Z) System for Designating Alkene Diastereomers
Relative Stabilities of Alkenes
Cycloalkenes
Synthesis of Alkenes via Elimination Reactions
Dehydrohalogenation of Alkyl Halides
Acid-Catalyzed Dehydration of Alcohols
Carbocation Stability and the Occurrence of Molecular Rearrangements
The Acidity of Terminal Alkynes
Synthesis of Alkynes by Elimination Reactions
Replacement of the Acetylenic Hydrogen Atom of Terminal Alkynes
Alkylation of Alkynide Anions
Hydrogenation of Alkenes and Alkynes
An Introduction to Organic Synthesis
Laboratory Experiment (7): Preparation of Cyclohexene, E5A
VIII. Alkenes and Alkynes II: Addition Reactions
A. Addition Reactions of Alkenes
B. Electrophilic Addition of Hydrogen Halides to Alkenes: Mechanism and Markovnikov's Rule
C. Stereochemistry of the Ionic Addition to an Alkene
D. Addition of Sulfuric Acid to Alkenes
E. Addition of Water to Alkenes: Acid-Catalyzed Hydration
F. Alcohols from Alkenes through Oxymercuration-Demercuration: Markovnikov Addition
G. Alcohols from Alkenes through Hydroboration-Oxidation: Anti-Markovnikov Syn Hydration
H. Protonolysis of Alkyboranes
I. Electrophilic Addition of Bromine and Chlorine to Alkenes
J. Stereospecific Reactions
K. Halohydrin Formation
L. Divalent Carbon Compounds: Carbenes
M. Oxidations of Alkenes: Syn 1,2-Dihydroxylation
N. Oxidative Cleavage of Alkenes
O. Electrophilic Addition of Bromine and Chlorine to Alkynes
P. Addition of Hydrogen Halides to Alkynes
Q. Oxidative Cleavage of Alkynes
R. How to Plan a Synthesis: Some Approaches and Examples
S. Laboratory Experiment (8): Preparation of Diphenylacetylene E6
IX. Nuclear Magnetic Resonance and Mass Spectrometry
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A.
B.
C.
D.
E.
F.
G.
H.
I.
J.
K.
L.
M.
N.
O.
P.
Q.
R.
Nuclear Magnetic Resonance (NMR) Spectroscopy
How to Interpret Proton NMR Spectra
Nuclear Spin: The Origin of the Signal
Detecting the Signal: Fourier Transform NMR Spectrometers
Shielding and Deshielding of Protons
The Chemical Shift: Equivalent and Nonequivalent Protons
Signal Splitting: Spin-Spin Coupling
Proton NMR Spectra and Rate Processes
Carbon-13 NMR Spectroscopy
Two-Dimensional (2D) NMR Techniques
Mass Spectrometry (MS)
Formation of Ions: Electron Impact Ionization
Depicting the Molecular Ion Fragmentation
How to Determine Molecular Formulas and Molecular Weights Using MS
Mass Spectrometer Instrument Designs
GC/MS Analysis
Mass Spectrometry of Biomolecules
Laboratory Experiment (9): Preparation of n-Butyl Bromide, E8A
X. Radical Reactions
A.
B.
C.
D.
E.
F.
G.
H.
I.
J.
K.
L.
Introduction: How Radicals Form and How They React
Homolytic Bond Dissociation Energies (DH°)
The Reactions of Alkanes with Halogens
Chlorination of Methane: Mechanism of Reaction
Chlorination of Methane: Energy Changes
Halogenation of Higher Alkanes
The Geometry of Alkyl Radicals
Reactions that Generate Tetrahedral Chirality Centers
Radical Addition to Alkenes: The Anti-Markovnikov Addition of Hydrogen Bromide
Radical Polymerization of Alkenes: Chain-Growth Polymers
Other Important Radical Reactions
Laboratory Experiment (10): Preparation of t-Butyl Chloride, E8B
XI. Alcohols and Ethers
A.
B.
C.
D.
E.
F.
G.
H.
I.
J.
K.
L.
M.
N.
O.
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Structure and Nomenclature of Alcohols and Ethers
Physical Properties of Alcohols and Ethers
Synthesis of Alcohols from Alkenes
Reactions of Alcohols
Alcohols as Acids
Conversion of Alcohols into Alkyl Halides
Alkyl Halides from the Reaction of Alcohols with Hydrogen Halides
Alkyl Halides from the Reaction of Alcohols with PBr3 or SOCl2
Tosylates, Mesylates, and Triflates: Leaving Group Derivatives of Alcohols
Chemistry of Alkyl Phosphates
Synthesis and Reactions of Ethers
Epoxides and the Sharpless Asymmetric Epoxidation
Reactions of Epoxides
Anti 1,2-Dihydroxylation of Alkenes via Epoxides
Environmentally Friendly Alkene Oxidation Methods
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P. Crown Ethers
Q. Laboratory Experiment (11): Relative Reactivity of Alkyl Halides, E8C
XII. Alcohols from Carbonyl Compounds: Oxidation-Reduction and Organometallic
Compounds
A.
B.
C.
D.
E.
F.
G.
H.
I.
J.
K.
Structure of the Carbonyl Group
Oxidation-Reduction Reactions in Organic Chemistry
Alcohols by Reduction of Carbonyl Compounds
Alcohol Dehydrogenase - A Biochemical Hydride Reagent
Stereoselective Reductions of Carbonyl Groups
Oxidation of Alcohols
Organometallic Compounds
Preparation and reactions of Organolithium and Organomagnesium Compounds
Alcohols from Grignard Reagents
Protecting Groups
Laboratory Experiment (12): Kinetic Study - the Hydrolysis of t-Butyl Chloride E8D
XIII. Conjugated Unsaturated Systems
A.
B.
C.
D.
E.
F.
G.
H.
I.
J.
K.
L.
M.
Allylic Substitution and the Allyl Radical
The Chemistry of Allylic Bromination
The Stability of the Allyl Radical
The Allyl Cation
Resonance Theory Revisited
Alkadienes and Polyunsaturated Hydrocarbons
1,3-Butadiene: Electron Delocalization
The Stability of Conjugated Dienes
Ultraviolet-Visible Spectroscopy
Electrophilic Attack on Conjugated Dienes: 1,4 Addition
The Diels-Alder Reaction: A 1,4-Cycloaddition Reaction of Dienes
Laboratory Experiment (13): E5B Dehydration of 3-Methyl-3-Pentanol and GC Analysis
Laboratory Experiment (14): E7A Reaction of Anthracene with Maleic Anhydride
Assignments and Grading Criteria
[Insert. Must include the value of each project, skill, exam, etc. as it relates to the final grade.]
Policies
Attendance policy: [Insert]
Late work/make-up policy: [Insert]
Weekly Course Schedule
[Insert date of each class meeting, topics to be covered, assignment due dates, testing dates, final exam
date, etc. Table format below is optional.]
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Dates of
Class
Meetings
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Teaching Schedule
The scheduling of the activities and teaching strategies on this syllabus, but not the objectives or content,
may be altered at any time at the discretion of the instructor.
Withdrawals: The last day to drop this course is [Insert date according to Important Class Dates for term
https://catalog.mchenry.edu/syllabi/Pages/default.aspx]. Failure to attend class does not constitute official
withdrawal. If students are considering a withdrawal, they should consult directly with the instructor and an
academic advisor. Students may withdraw from a class through the Registration Office, either in person or by
fax: (815) 455-3766. In their request, students should include their name, student ID number, course prefix,
number and section, course title, instructor, reason for withdrawing, and their signature. Withdrawal from a
course will not be accepted over the telephone.
Academic Support for Special Populations Students
Students with Disabilities:
It is the policy and practice of McHenry County College to create inclusive learning
environments. If you are a student with a disability that qualifies under the American with
Disabilities Act – Amended (ADAA) and require accommodations, please contact the Access
and Disability Services office for information on appropriate policies and procedures for
receiving accommodations and support. Disabilities covered by ADAA may include learning,
psychiatric, and physical disabilities, or chronic health disorders. Students should contact the
Access and Disability Services office if they are not certain whether a medical
condition/disability qualifies. To receive accommodations, students must make a formal request
and must supply documentation from a qualified professional to support that request. However,
you do not need to have your documentation in hand for our first meeting. Students who
believe they qualify must contact the Access and Disability Services office to begin the
accommodation process. All discussions remain confidential. The Access and Disability
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Services office is located in Room A260 in A Building in the Atrium. To schedule an
appointment to speak with the manager, please call (815) 455-8766. Information about
disabilities services at MCC can be found at: www.mchenry.edu/access
Additional syllabus information and resources can be found at www.mchenry.edu/syllabusinfo.
STUDENTS ARE RESPONSIBLE FOR KNOWING ALL SYLLABUS INFORMATION.
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