Chemistry 222 – 2M
Organic Chemistry II
Spring 2009
Instructor: Dr. Jeremy Wessel
Office Phone: (985) 448-4504
Office Hours: 9:40-11:40 MWF, 1:00-3:00 TF
Office: Pel 245C
E-mail: phsc-jjw@nicholls.edu
Catalog Description: CHEM 222. Organic Chemistry II. 3-3-0. Prerequisite: C or better in CHEM
221. A continuation of CHEM 221.
Prerequisite: C or better in CHEM 221.
Required Textbooks and Other Materials: Organic Chemistry by T.W. Graham Solomons and
Craig B. Fryhle, 9th ed. Wiley (2008)
 Molecular Model Kit
 iClicker
 Homework will be done on the WileyPlus website. Class URL is
http://edugen.wiley.com/edugen/class/cls85477/
Required Supplemental Readings: None
Optional Supplemental Readings: There are supplemental books available which you may find
helpful, including Organic Chemistry II as a Second Language: Second Semester Topics by
David R. Klein.
General Education Student Learning Outcomes
CHEM 222, as a Core Curriculum course, fulfills three hours of general education requirements
in the area of the natural sciences and is thus designed to enable students to meet the following
broad outcome for all the natural sciences:
Goal: Upon completion of the undergraduate curriculum, students will be able to comprehend and
to apply the basic principles of science and methods of scientific inquiry.
For further explanation of the learning objectives associated with this goal, go to
http://www.nicholls.edu/gened/goals_objectives.html.
CHEM 222 meets this goal by the following course-specific student learning outcomes:
Course Goals:
The student will develop an understanding of:
1. Representative reactions involving different classes of organic compounds
2. The concept of aromaticity
Student Outcome Objectives
At the end of the class the student will be able to:
 identify and name organic compounds, using the proper nomenclature for the various
classes of compounds
 show the products of reactions
 write a reaction sequence showing how to produce a desired product (i.e. synthesis)
 use Hückel’s rule to determine if species are aromatic or antiaromatic
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demonstrate a knowledge of electrophilic aromatic substitution, including substituent
effects
demonstrate a knowledge of organometallic compounds and their uses in synthesis
demonstrate a knowledge of nucleophilic addition to carbonyl compounds and
epoxides
demonstrate a knowledge of the oxidation of alcohols
demonstrate a knowledge of oxidation and reduction of carbonyl compounds
demonstrate a knowledge of enols and enolates and their reactions
demonstrate an understanding of substituent effects on acidity and basicity
demonstrate an understanding of nucleophilic acyl substitution including the relative
reactivity of carboxylic acid derivatives
demonstrate an understanding of the use of enolates for carbon-carbon bond
formation
demonstrate a knowledge of amines including methods of preparation and reactions
Course Content:
Chapter 11: Alcohols and Ethers
Nomenclature of ethers and epoxides, conversion of alcohols to alkyl halides, sulfonate leaving
groups, etherification of alcohols, Williamson ether synthesis, silyl ethers, acid-catalyzed
cleavage of ethers, epoxidation, ring-opening of epoxides.
Chapter 12: Alcohols From Carbonyl Compounds
Oxidation-reduction reactions in organic chemistry, alcohols by reduction of carbonyl
compounds, oxidation of alcohols, preparation of organolithium and Grignard compounds and
their use in synthesis
Chapter 13: Conjugated Unsaturated Systems
Allylic radical substitution, electrophilic addition to conjugated dienes, Diels-Alder reaction,
Chapter 14: Aromatic Compounds
Nomenclature of benzene derivatives, structure and bonding in benzene, Hückel’s rule,
aromaticity and antiaromaticity, aromatic ions, heterocyclic aromatic compounds
Chapter 15: Reactions of Aromatic Compounds
Mechanisms and products of electrophilic aromatic substitutions: halogenation, nitration,
sulfonation, Friedel-Crafts; reduction of acylbenzenes; substituent effects on regioselectivity and
rate, regioselective synthesis, reactions of aromatic side chains, Birch reduction.
Chapter 16: Aldehydes and Ketones I: Nucleophilic Addition to the Carbonyl Group
Nomenclature of aldehydes and ketones, preparation of aldehydes by oxidation and reduction,
synthesis of ketones, nucleophilic addition of water, HCN, alcohols, amines; Wittig reaction.
Oxidation of aldehydes.
Chapter 17: Aldehydes and Ketones II: Enols and Enolates
Enolization. Reactions of enols and enolates: -Halogenation, Haloform reaction, aldol
condensation and similar reactions, lithium enolates and alkylation, selenation, addition to 
unsaturated carbonyl compounds, Michael reaction.
Chapter 18: Carboxylic Acids and Their Derivatives
Nomenclature of carboxylic acids and derivatives, physical properties of carboxylic acids, acidity,
salts, preparation of carboxylic acids and derivatives, interconversion of carboxylic acids and
derivatives, carbonic acid derivatives, decarboxylation
Chapter 19: Synthesis and Reactions of -Dicarbonyl Compounds
Claisen condensations, acylation of ketones, acetoacetic ester synthesis, malonic ester synthesis,
barbiturates; alkylation of esters, nitriles and dithianes; Mannich reaction, enamine reactions,
Michael addition.
Course Requirements:
Exams - There will be 4 hour exams (on chapters 11-13, 14-15, 16-17, 18-19) at 100 pts. each.
The 200 pt. final will be comprehensive.
Problems – Done on Wiley Plus. Points received = Total # of Wiley Plus pts. divided by 10.
Organic Chemistry “Scavenger Hunt” – 25 pts. See Blackboard for full details.
Method of Evaluation: Grades will be determined using the following scale:
A: 90-100
B: 80-90
C: 70-80
D: 60-70
F: <60
This scale may be adjusted downward if the class average is low. If the student’s grade on the
comprehensive final is higher than the student’s average up to that point, the grade on the final
exam will be the grade for the course.
Academic Dishonesty Policy: Any student found cheating will be subject to the penalties stated in
Student Code of Conduct; including, but not limited to, a score of zero on exam, expulsion from
the class, or expulsion from the University.
Attendance Policy: No excuses are necessary for missing class. The student is responsible for
making up any missed work. Attendance is essential to doing well in the course.
Make-up Policy: Missed exams should be made up as soon as possible. Exams can be made up
for an excused absence only.
Academic Disabilities Policy: If you have a documented disability that requires assistance, you
will need to register with the Office of Disability Services for coordination of your academic
accommodations. The Office of Disability Services is located in Peltier Hall, Room 100-A. The
Phone Number is (985) 448-4430 (TDD 449-7002).
Academic Grievances:
The proper procedure for filing grade appeals or grievances related to academic matters is listed
in Section 5 of the Code of Student Conduct and at the following link:
http://www.nicholls.edu/documents/student_life/code_of_conduct.pdf.
Continued Learning following an Extreme Emergency
The following guidelines are meant: to help the business of education continue at Nicholls State
University in the aftermath of an extreme emergency situation; to help faculty and students
understand their roles in completing education requirements for courses in progress when the
emergency began; and to encourage faculty to be imaginative and resourceful in finding ways to
continue the education of students and the work of the university.
Faculty responsibilities:
• Faculty members are responsible for their development in the use of the Blackboard software.
• Faculty members are responsible for having a plan for continuing their courses using only
Blackboard and email.
• Faculty members should be allowed to continue their course in whatever way suits the
completion of the course best, and encouraged to be creative in the continuation of these courses.
• Any adjustments or compensations made to a student’s progress in special programs with labs,
clinical sequences (i.e. Culinary, Nursing, etc.), or the like should be made only in the immediate
semester following the emergency.
 Faculty members are responsible for including these guidelines in all syllabi.
Student responsibilities:
• Students are responsible for reading regular emergency notifications on the NSU website.
• Students are responsible for knowing how to use and access Blackboard.
• Students are responsible for being familiar with emergency guidelines.
• Students are responsible for evacuating textbooks and other course materials.
• Students are responsible for knowing their Blackboard login and password
• Students are responsible for contacting faculty regarding their intentions for completing the
course.
NOTE: Faculty and students should be open, flexible, and show compassion in determining the
precise course of action.
Semester Withdrawals: The last day to withdraw from the class with a ‘W’ is April 3, 2009.
Class Disruptions are not tolerated. The use of cell phones, pagers and/or any other electronic
personal device in class is prohibited. Any infractions will result in the dismissal from class.