Syllabus for CHEMISTRY 304 at LeMoyne-Owen College
ORGANIC CHEMISTRY II
Description: A study of the preparation, properties, nomenclature and reactions of aldehydes, ketones,
carboxylic acids and aromatic compounds. Three lecture hours.
Prerequisite: CHEM 303 with a grade of C or better
General Information: Organic chemistry is a transferable college level sequence which is required in many
science programs including pre-medicine, pre-dentistry, pre-engineering, pre-pharmacy and pre-veterinary
medicine. Consequently, it is a comprehensive survey of the field of organic chemistry with considerable stress
placed on the classes, structures, nomenclature and reactions of organic compounds.
Instructor:
Dr. Sherry Painter
email: sherry_painter@loc.edu
phone: 901-435-1383
office: GOH 400B
Office Hours: Monday, Wednesday, and Friday: 10:00 – 11:00 AM
Monday & Wednesday: 1:00 – 3:00 PM
Tuesday: 12:30 – 2:00 PM
Thursday: 9:00 – 11:00 AM
Required Materials:
Textbook: Organic Chemistry; L.G. Wade; Prentice Hall Publishing Bundled with ACE Organic Passcode
**ACE Organic Access Passcode – comes bundled with the textbook if bought new from the bookstore.
Otherwise, you can obtain the passcode by clicking here: Purchase ACE Organic
(https://register.pearsoncmg.com/reg/buy/buy1.jsp?productID=27976) The purchase
price is ~ $35.00.
Optional Materials:
Official Study Guide for the American Chemical Society Organic Chemistry Exam: This may be
purchased online by clicking here: Purchase ACS Organic Chemistry Study Guide
(http://www4.uwm.edu/chemexams/order/SG_2008_form.pdf ) A copy of this study guide is also
available on reserve at the Hollis F. Price Library.
Objectives: This course is designed for science majors. Students will be able to demonstrate problem solving
approaches fundamental to chemistry. Students will be able to use chemical nomenclature for organic
compounds appropriately. Students will become familiar with bonding and molecular structure and with
writing reactions for organic reactions.
Outcome Statements:
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Understand the nomenclature of dienes.
Understand the term conjugated.
Determine the order of stability of related dienes.
Describe the bonding in conjugated dienes using principles of valence bond and molecular orbital theory.
Distinguish between 1,2 and 1,4 addition of electrophiles to dienes
Use resonance forms to predict the products of addition of electrophiles to dienes.
Discuss the concept of thermodynamic vs. kinetic control of reaction products.
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Discuss the Diels-Alder reaction and the concept of pericyclic reactions
Distinguish between endo and exo stereochemistry.
Define the role of a dienophile in the Diels Alder reaction..
Understand the effect of inductive effects on the reactivity of dienophiles
Understand the concept of s-trans and s-cis conformations of dienes.
Understand the concept of aromaticity
Give the common and IUPAC names for aromatic compounds
Understand the terms ortho, para, and meta as they apply to aromatic compounds..
Understand the mechanism of electrophilic substitution reactions of aromatic compounds.
Discuss the concept of directing groups in electrophilic substitution reactions of aromatic compounds.
Use the concept of resonance to predict the product of an electrophilic substitution reaction of an aromatic compound.
Describe the structure of aromatic compounds in terms of molecular orbital theory.
Understand the Huckle rule for predicting aromaticity or anti-aromaticity.
Discuss the aromaticity of heterocyclic compounds.
Recognize activating and deactivating groups for electrophilic substitution reactions of aromatic compounds.
Describe inductive and resonance effects in substitution reactions of aromatic compounds.
Write reaction products for the reaction of aromatic compounds with electrophiles.
Understand the mechanism of Friedel Craft alkylation of aromatic compounds.
Discuss the concept of hydride and alkyl group shifts in alkylation reactions.
Use additive effects to predict products of substitution reactions of di-substituted aromatic compounds.
Understand the concept of nucleophilic substitution of aromatic compounds.
Understand the concepts of benzyne intermediates in elimination/addition mechanisms of aromatic compounds.
Develop synthetic strategies for the synthesis of trisubstituted aromatic compounds.
Give the IUPAC and common names of alcohols and phenols.
Describe the properties of alcohols and phenols.
Understand the factors influencing the acidity of alcohols and phenols.
Discuss methods of preparing alcohols and phenols.
Understand the Grignard reaction for preparing alcohols.
Describe the reactions of alcohols
Understand the mechanism of the dehydration of alcohols with POCl3
Discuss the conversion of alcohols into tosylates.
Discuss the oxidation of alcohols to carbonyl compounds.
Describe Corey's reagent for the oxidation of alcohols to aldehydes
Understand the concept of protecting groups in synthetic strategies.
Understand the use of Fischer projections for carbohydrates.
Describe the characteristic IR and NMR absorptions of alcohols and phenols.
Discuss the properties of ethers, epoxides, thiols and sulfides.
Understand the nomenclature of ethers, thiols and sulfides.
Understand the mechanism for the alkoxymercuration of alkenes.
Discuss the Williamson synthesis of ethers.
Describe the acid catalyzed cleavage of ethers.
Understand the mechanism of the Claisen rearrangement.
Understand the acid and base catalyzed ring opening reactions of epoxides.
Describe methods for synthesizing thiols and sulfides.
Describe the IR and NMR spectra of ethers.
Understand the nomenclature of aldehydes and ketones.
Write reactions for the oxidation of aldehydes to carboxylic acids.
Understand the use of DIBAH for the preparation of aldehydes.
Understand reaction mechanisms for the nucleophilic addition reactions of aldehydes and ketones.
Discuss reactivity patterns of aldehydes and ketones.
Understand the use of acetals as protecting groups for carbonyl compounds.
Understand reaction mechanisms for imine and eneamine formation.
Describe and understand the mechanism of the Wolf-Kishner reaction.
Describe and understand the mechanism of the Wittig reaction.
Discuss 1,4 addition of nucleophiles to alpha-beta unsaturated carbonyl compounds.
Describe the IR and NMR spectra of carbonyl compounds.
Understand the nomenclature of carboxylic acids.
Discuss the substituent effects on the acid properties of carboxylic acids.
Write reactions for the preparation of carboxylic acids, including the carboxylation of Grignard reagents.
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Write the reaction for the reduction of carboxylic acids with LAH.
Discuss the dehydration of amides to produce nitriles.
Understand the reaction mechanism for the hydrolysis of nitriles.
Discuss the reactions of nitriles to form ketones, amines, and amides.
Understand the IR and NMR spectra of carboxylic acids and carboxylic acid derivatives..
Discuss the nomenclature of acyl halides, anhydrides, esters and amides.
Understand the reaction mechanism for nucleophilic acyl substitution reactions.
Determine the relative reactivity of carboxylic acid derivatives.
Predict the reaction products of nucleophilic acyl substitutions.
Write reactions for the preparation of carboxylic acid derivatives (acid halides, anhydrides, esters, and amides)
Discuss the structure of lactones and lactams.
Understand the reaction mechanism for the enolization of a ketone or aldehyde.
Understand the reaction mechanism for the alpha halogenation of a ketone or aldehyde.
Describe the formation of enolates in terms of acid - base chemistry.
Discuss the use of LDA in the formation of enolates.
Describe the chemistry of enolates with electrophiles.
Understand C vs. O alkylation of enolates.
Describe the haloform reaction.
Understand the mechanism of the malonic ester synthesis.
Understand the mechanism of the acetoacetic ester synthesis.
Describe the direct alkylation of enolates.
Understand the mechanism of the aldol reaction.
Understand the mechanism of the Claisen and Dieckmann condensation reactions..
Understand the mechanism of the Michael reaction.
Describe the Robinson annulation method for the synthesis of polycyclic molecules.
Describe the concept of pyramidal inversion and the consequences for chirality in amines.
Describe the properties of amines.
Write reactions for the synthesis of amines.
Describe the Gabriel synthesis of primary amines.
Describe the reductive amination of carbonyl compounds.
Describe the Hoffman elimination
Understand the terms Hoffman product and Zaitsev product.
Understand the directing effect of the amine group in aromatic electrophilic substitution reactions.
Describe the diazo coupling reaction to form azo dyes.
Understand the IR and NMR spectra of amines.
Identify unknown compounds using IR, NMR and MS spectral data.
Develop synthetic strategies using the reactions covered in the syllabus
Understand the concept of retrosynthetic strategy for planning multistep synthesis.
Method of Instruction: Lecture, discussion, computer-assisted learning, student homework assignments and
independent literature research will be utilized in this course. Students are encouraged to communicate with the
instructor via email and to take full advantage of the instructor’s office hours.
Grades: Grades will be assigned as follows:
A:
B:
C:
D:
F:
90% – 100%
80% - 89%
70% - 79%
60% - 69%
0 – 59%
Superior
Above Average
Average
Below Average
Failing
The grades in this chemistry courses will be determined according to the following approximate weighting
scheme:
Exams:
Presentation
55%
10%
Daily work & Quizzes (Online & In-class) 20%
Comprehensive Final:
15%
One requirement of the course is that every student take the final examination. The final exam is the ACS
national standardized exam that covers material from both organic I and organic II. Study materials for this
exam can be purchased online. For information about the exam and how to order study guides, go to
http://www3.uwm.edu/dept/chemexams/. Failure to take the final examination will result in a grade of F for the
course. In the case where a final examination is missed and the instructor has been notified in advance, it may
be possible (at the discretion of the instructor) for the student to receive a grade of I. However, a grade of I must
be converted to another letter grade by completing work prior to the deadline of the succeeding semester,
otherwise the I will be automatically converted to a grade of F.
Attendance: Attendance at all lecture meetings is expected. Persistent unexcused absences exceeding 15% of
the lecture meetings may result in a reduction of the student’s grade. If unexcused absences exceed 20% of the
lecture meetings, the instructor may award the student the grade of an F. See the College Catalog for the last
day to withdraw from the course or the College without penalty, and for a further explanation of the attendance
policy.
Make-up Tests: At the discretion of the instructor, one missed test will be handled in the following manner:
1. The comprehensive final exam will be substituted for the missed test.
OR
2. A make-up test will be given during the end of the semester final examination period, at a time chosen by the
instructor, (not the scheduled final examination time for the course), over the material covered on the missed
test.
Any other test missed will incur a grade of zero (0).
Electronic Devices: All electronic communication devices must be in
silent mode (or
off) AND out of sight. The use of cell phones or other electronic
communication devices during class is prohibited. It is not acceptable to exit the class to answer the
phone. If you have an emergency and are expecting a call, please inform the instructor before class
begins. Otherwise, cell phones should be OFF during the entire class period. Ear buds, Blue Tooth,
BlackBerry’s or any other communication devices are not to be worn during class. Also note, that the use
of your cell phone as a calculator is not allowed.
Cheating: Cheating on a test or exam will incur a grade of zero on that test or exam. See the Student
Handbook for further explanation concerning Academic Honesty.
Recommended Problems: Doing these problems and exercises are strongly encouraged as it is not unusual for
questions or problems similar to those assigned to appear on tests or examinations. “Taking organic chemistry
without working the problems is like skydiving without a parachute. Initially, there is a breezy sense of
freedom and daring. But then, there is the inevitable jolt that comes at the end for those who went
unprepared.” ~ L. G. Wade
ACS Review Quizzes: ACS review quizzes will be given weekly through ACE Organic and will be due each
Friday. There are no make-up quizzes. Quiz topics will be as follows: 1) Nomeclature, 2) Nucleophilic
Substitution and Elimination, 3) Structure, Hybridization, Resonance, & Aromaticity 4) Stereoisomerism 5)
Electrophilic Addition 6) Electrophilic and Nucleophilic Substitution 7) Nucleophilic Addition at Carbonyls 8)
Free Radical Substitution 9) Spectroscopy 10) Enols and Enolates 11) Oxidation and Reduction 12) Quiz:
Acids & Bases 13) Nucleophilic Substitution & Addition at Carbonyls 14) Synthesis & Analysis
Policies Related to Students With Disabilities: If you have special needs or considerations which must be
taken into account for you to be successful in this class, you should see Ms. Saulsberry and then meet with the
instructor as soon as possible.
Other Regulations: A student is bound by all rules and regulations appearing in the Student Handbook.
2011
Class
Dates
Class
Day
Lecture Outline for CHEM 304
(Spring 2011: class meets TTh at 11:00 – 12:15 PM in GOH 414)
Topic:
1/13
Th
Review
1/18
T
Chapter 9 – Alkynes
1/20
Th
Chapter 10 – Structure and Synthesis of Alcohols
1/25
T
Chapter 11 – Reactions of Alcohols
1/27
Th
Chapter 14 – Ethers, Epoxides, and Sulfides
2/1
T
2/3
Th
Exam #1 - Chapters 9, 10, 11, & 14
2/8
T
Chapter 15 - Conjugated Dienes
2/10
Th
Chapter 16 – Aromatic Compounds
2/15
T
Chapter 17 – Reactions of Aromatic Compounds
2/17
Th
2/22
T
Exam #2 - Chapters 15, 16, & 17
2/24
Th
Chapter 18 - Ketones & Aldehydes
3/1
T
3/3
Th
Chapter 19 - Amines
3/8
T
Chapter 20 - Carboxylic Acids
3/10
Th
3/15
T
Exam #3 – Chapters 18, 19, & 20
3/17
Th
Chapter 21 - Derivatives of Carboxylic Acids
3/22
T
3/24
Th
3/29
T
3/31
Th
Chapter 22 – Substitutions of Carbonyls
Exam #4 – Chapters 21 & 22a
Chapter 22 – Condensation of Carbonyls
4/5
T
4/7
Th
4/12
T
Chapter 23: Biomolecules – Carbohydrates & Nucleic Acids
4/14
Th
Chapter 24: Biomolecules – Proteins, Chapter 25: Biomolecules - Lipids
4/19
T
4/21
Th
Exam #5 – Chapters 22b, 23, 24, & 25
4/26
T
Practice mini ACS Exam
4/27
W
Review Day
4/28
Th
Final Exam - Comprehensive ACS Exam – Thursday April 28, 2011 (10:00-11:50)