ORGANIC CHEMISTRY II
CHM 266- 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: CHM914
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 II is a continuation of Organic Chemistry I. It includes an in-depth study of the
descriptive chemistry of functional groups, reaction mechanisms, applications of mass and infrared
spectroscopy to structure determinations, and carbohydrate and protein chemistry. Laboratory work
focuses on the preparation and identification of organic compounds.
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 265 with a grade of C or higher.
Section Notes:
[Insert if desired]:
Course Objectives:
Cognitive: The student will be able to:
1. Interpret uv-visible spectra.
2. Describe the chemistry of alcohols, thiols, phenols, ethers, aldehydes, ketones, carboxylic acids,
and amines.
3. Use carbonyl substitution and condensation reactions in synthesis.
4. Describe the chemistry of aromatic compounds.
5. Compose synthetic routes to organic compounds.
6. Use curved arrow notation to describe the mechanisms of organic reactions.
7. Describe the chemistry of amino acids and carbohydrates.
Affective: The student will be able to:
1. Realize the importance of understanding the mechanisms in organic reactions.
2. Realize the importance of organic chemistry in the study of biochemistry and biology.
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3. Develop a concern for chemical safety.
Manipulative: The student will be able to:
1. Demonstrate the ability synthesize and characterize organic compounds.
2. Develop the ability to purify organic compounds by distillation and fractional crystallization.
3. Be able to use computer spreadsheets.
Course Outline:
Text : Organic Chemistry by John McMurry
I.
II.
III.
IV.
V.
Week 1: Chapter #14 Conjugated Dienes and Ultraviolet Spectroscopy
A. Preparation of Conjugated Dienes
B. Stability of Conjugated Dienes
C. Electrophilic Addition Reactions of Conjugated Dienes
D. The Diels-Alder Reaction
Laboratory Experiment Dichlorocarbene
Week 2: Chapter #16- Benzene and Aromaticity
A. Nomenclature of Aromatic Compounds
B. Aromaticiy and the Huckel 4n + 2 rule
C. Aromatic Ions
D. Naphthalene and Pyridine
Laboratory Experiment: Diels-Alder Reaction
Week Three: Chapter #16
Chemistry of Benzene: Electrophilic Aromatic Substitution
A. Electrophilic Aromatic Substitution Reactions
B. Friedel-Crafts Alkylation and Aceylation Reaction
C. Substituent Effects
D. Nucelophilic Aromatic Substitution
E. Benzyne
F. Oxidation and Reduction of Aromatic Compounds
Laboratory: Nitration of Methyl Benzoate
Week Four: Chapter #17 Alcohols and Phenols
A. Nomenclature of Alcohols and Phenols
B. Properties of Alcohols and Phenols
C. Reactions of Alcohols and Phenols
D. Preparation and Reactions of Phenols
Laboratory: Alkylation of Meisitylene
Week Five: Chapter #18 Ethers and Epoxides: Thiols and Sulfides
A. Preparation of Ethers
B. Reactions of Ethers
C. Preparation and Reactions of Epoxides
D. Crown Ethers
E. Spectroscopy of Ethers
Thiols and Sulfides Laboratory: Oxidation Reactions
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VI.
VII.
VIII.
IX.
X.
Week Six: Chapter #19 Aldehydes and Ketones
A. Nomenclature of Aldehydes and Ketones
B. Preparation of Aldehydes and Ketones
C. Nucleophilic Addition Reaction of Aldehydes and Ketones
D. Reaction of Aldehydes and Ketones with Grignard Reagents
E. Nucelophilic Addition Reactions of Amines
F. Acetyl Formation
G. The Wittig Reaction
H. Conjugate Nucleophilic Addition to -Unsaturated Aldehydes and Ketones
Laboratory: Grignard Synthesis
Week Seven: Chapter #19 and Chapter #20 Lipids
A. The Structure and Properties of Triglycerides
B. Complex Lipids
C. Membranes
D. Glycerophospholipids, Sphingolipids, and Glycolipids
E. Steroids and Steroid Hormones
F. Bile Salts
G. Prostaglandins, Throboxans and Leukotrienes
Laboratory: Preparation of Esters
Week Eight: Chapter #20 Carboxylic Acids
A. Nomenclature of Carboxylic Acids
B. Acidity of Carboxylic Acids
C. Substituent Effects on Acidity
D. Preparation of Carboxylic Acids
E. Reactions of Carboxylic Acids
F. Reduction of Carboxylic Acids
G. Spectroscopy of Carboxylic Acids
Laboratory: The Perkin Reaction
Week Nine: Chapter #21 Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution
A. Naming Carboxylic Acids Derivatives and Nitriles
B. Nucleophilic Acyl Substitution Reactions
C. Chemistry of Acid Halides
D. Chemistry of Esters
E. Chemistry of Amides
F. Chemistry of Nitriles
G. Thiol Esters
H. Polyamides and Polyesters
Laboratory: Esterification and Hydrolysis
Week Ten: Chapter #22 Carbonyl Alpha-Substitution Reactions
A. Keto-Enol Tautomerism
B. Mechanism of Alpha-Substitution Reaction
C. The Hell-Volhard-Zelinskii Reaction
D. Enolate Ion Formation
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XI.
XII.
XIII.
XIV.
E. The Haloform Reaction
F. Alkylation of Enolate Ions
Laboratory: Amines
Week Eleven: Chapter #23
Carbonyl Condensation Reactions
A. Mechanism of Carbonyl Condensation Reactions
B. The Aldol Condensation
C. Dehydration of Aldol Products
D. Mixed Aldol Reactions
E. Intermolecular Reactions
F. Claisen Condensations
G. The Dieckmann Cyclization
H. The Michael Reaction
I. The Stork Enamine Reaction
J. The Robinson Annulation Reaction
Laboratory: Separation and Purification of an Analgesic Tablet
Week Twelve: Chapter #24 Amines
A. Nomenclature of Amines
B. Structure and Bonding in Amines
C. Properties of Amines
D. Synthesis of Amines
E. Reactions of Amines
F. Reactions of Aryl Amines
G. Spectroscopy of Amines
Laboratory: Isolation of Lycopene and Carotene
Week Thirteen: Chapter #25 Biomolecules: Carbohydrates
A. Classification of Carbohydrates
B. Configuration of Monosaccharides: Fisher Projections
C. Configuration of Aldoses
D. Cyclic Structures of Monosaccharides
E. Mutarotation
F. Reactions of Monosaccharides
G. Stereochemistry of Glucose
H. Disaccharides
I. Polysaccharides
Laboratory: The Synthesis of Natural Products
Week Fourteen: Chapter #26 Biomolecules: Amino Acids, Peptides, and Proteins
A. Structure of Amino Acids
B. Isoelectric Points
C. Synthesis of Amino Acids
D. Peptides and Proteins
E. Analysis of Proteins
F. Synthesis of Proteins
G. Classification of Proteins
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H.
I.
J.
K.
XV.
Protein Structure
Enzymes
Mechanism of Enzyme Action
Protein Denaturation
Laboratory: Carbohydrates and Sweeteners
Week Fifteen: Chapter #30 Orbitals and Organic Chemistry: Percyclic Reactions
A. Molecular Orbitals in Conjugated pi Systems
B. Molecular Orbitals in Percyclic Reactions
C. Stereochemistry of Thermal Electocyclic Reactions
D. Photochemical Electrocyclic Reactions
E. Cycloaddition Reactions
F. Sigmatropic Rearrangements
Laboratory: Polymers: Synthesis and Recycling
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.]
Dates of
Class
Meetings
Week #1
Week #2
Week #3
Week #4
Week #5
Week #6
Week #7
Week #8
Week #9
Week #10
Week #11
Week #12
Week #13
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Course Schedule
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Week #14
Week #15
Week #16
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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 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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