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Chemistry 261/263 Sections 1-2
CHE 261/263 - Organic Chemistry II
Summer 2010
Lectures: M-Th (10:00 – 11:45 am), JE114
Laboratory: M, W (5:45 – 9:35 pm) and T, Th (1:10-500 pm), JE325
Lecturer: Adiel Coca, Ph.D.
Office: 304 Jennings Hall
Phone: 203 – 392 - 6982
E-mail: cocaa2@southernct.edu
Office Hours: M-Th (11:45 am – 12:45 pm) or by appointment
Required Texts:
 McMurray, J. Organic Chemistry, 7th ed. with NOW, 2008, Brooks/Cole
Publisher.
 Molecular Model Kit (two options available in the bookstore).
 Goggles (available from chemistry club).
 Hardcover Lab Notebook
Optional Material:
 Traynham, J. G. Organic Nomenclature: A programmed Introduction, 5th ed.,
1997, Prentice Hall Publisher.
 McMurray, S. Study Guide and Student Solutions Manual for Organic Chemistry,
7th ed., 2008, Brooks/Cole Publisher.
 Weeks, D. Pushing electrons.
Your course grade is based on the following criteria
CHE 261:
 class participation, 3%
 Three exams, 24% each
 Laboratory grade, 25%. All projects must be completed and a passing grade
(≥60%) must be received in the laboratory component of the course in order to
receive a passing grade in the course!!!
CHE 263:
 class participation, 3%
 Three exams, 32.3% each
The course grade will be based on the grading scale below with possible adjustments at
the instructor's discretion:
A+ (100-96)
A (95-91)
A- (90-86)
B+ (85-82)
B (81-78)
B- (77-74)
C+ (73-70)
C (69-66)
C- (65-62)
D+ (61-58)
D (57-54)
D- (53-50)
F <50
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Your grade will not be based upon any claimed “need” which you may have. It is
incumbent upon you, the student, to perform at the level that will fulfill the specific
“need.” In addition, there is no provision in this course to do work for “extra credit.”
Exams (Target dates):
 1st exam: Thursday, 7/15/10 – Covering chapters 11, 17, 18, 19 (first half)
 2nd exam: Tuesday, 7/27/10 – Covering chapters 19 (second half), 20, 21, 22
 3rd exam: Thursday, 8/5/10 – Covering chapters 23, 15, 16, 24.
The exams will be taken during regular class time. Students who arrive late will not be
allotted extra time. Any changes will be announced in class. Only students with valid
excuses will be permitted to take the make-up exam. Conflicts in scheduling should be
resolved in advance (at least one week before the exam). All exams will be
comprehensive written tests (but they will concentrate on the material covered since the
previous test). They will be constructed in such a way as to emphasize active
understanding of the material. Books, scratch paper (other than furnished), cell phones
(and similar electric devices), and calculators will not be allowed. The use of a molecular
model kit is limited to only one carbon with four bonds during examination.
Helpful Hints. Organic Chemistry is a difficult course. It covers a lot of demanding
material. Here are some tips to do well in this course:
 study everyday, do reviews weekly
 read the material before the lecture.
 solve as many end-of-chapter problems as possible (resort to answer book only
after you have attempted the problem).
 study with a friend; if you can explain a concept to your study mate, you
understand it
 just reading and understanding the material (passive understanding) is
insufficient; you should be able to use the just learned concepts in situations not
previously encountered, and make logical connections with concepts learned
previously (active understanding)
 constantly probe your understanding by asking (and answering) question "why?"
in relation to all statements and logical constructions
 do not fall behind in your study; it is virtually impossible to prepare well for the
exam in just a few days before it. Cramming for this course will not work!
Attendance:
Optional but highly recommended.
Academic Integrity:
All forms of academic dishonesty will not be tolerated. Such infractions are considered
cause, at the least, for awarding a grade of "0" on the assignment or exam in question.
For more details, see the student handbook on the subject. This policy will be strictly
enforced.
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Student Disabilities:
I believe in providing reasonable accommodations for students with documented
disabilities on an individualized and flexible basis. If you are a student with a
documented disability, the university’s Disability Resource Center (DRC) determines
appropriate accommodations through consultation with the student. Before you may
receive accommodations in this class, you will need to make an appointment with the
Disability Resource Center, located in EN C-105A. To speak with me about other
concerns, such as medical emergencies or arrangements in case the building must be
evacuated, please make an appointment as soon as possible.
CengageNOW:
It is strongly recommended that student routinely log-on to CengageNOW at
http://www.cengage.com/sso/ and work on the problems provided. Register by clicking
first on create my account, then register as a student, then enter the access code that
comes with your textbook, then provide the required information, and finally choose
SCSU as your institution. The “section key” is E-5WMMRF2CDBWJ8. These
assignments will not be graded, but will provide another resource for doing well in the
course.
Outline of Lectures: Tentative Schedule
1. Alkyl Halides: Nucleophilic Substitutions and Eliminations (4 lectures)
 SN1 and SN2
 E1 and E2
 Effects of solvent, substrate structure, and nucleophile (base) on reactivity
Sections covered: All Chapter 11
Assigned problems: 1-13, 15-20, 25-27, 29-31, 34-44, 47-52, 56-57, 61, 62, 65.
2. Alcohols and Phenols (3 lectures)
 Naming
 Preparation
 Reactions
 Protection
 Phenols
Sections covered: All of Chapter 17, Read 15.1
Assigned problems:
Chapter 15: 1: 1-3, 13, 18-19.
Chapter 17: 1, 2, 4-16, 21, 22 (except e), 23-25, 29-30, 31, 32 a, d, 33-38, 40a-c, 41, 44,
46-49, 51, 57, 68, 69.
3. Ethers and Epoxides; Thiols and Sulfides (2 lectures)
 Naming
 Preparation of ethers
 Reactions of ethers
 Ring-opening of epoxides
 Thiols and sulfides
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Sections covered: All of Chapter 18 except 18.4.
Assigned problems:
Chapter 17: 39.
Chapter 18: 1-9, 11-17, 19-27, 28 a,d, 29, 30, 32-34, 39-41, 43, 44, 50-52.
4. A preview of Carbonyls (0.5 lectures)
Sections covered: pg. 686-694.
Assigned problems: 1-3.
5. Aldehydes and Ketones: Nucleophilic Addition (4.5 lectures)
 Naming
 Preparation
 Reactions: Oxidation
 Reactions: Nucleophilic addition.
 Reactions: Conjugate nucleophilic additions
Sections covered: All of Chapter 19.
Assigned problems: 1-3, 4a, d, 5-17, 19-23, 27-30, 32-37, 39-45, 48-51, 56-57, 59, 62,
72, 73.
6. Caboxylic acids and Nitriles (2 lectures)
 Nomenclature
 Acidity
 Preparation
 Reactions Overview
 Nitriles
Sections covered: All of Chapter 20.
Assigned problems: 1-3, 6-7, 9-14, 17-19, 21-22, 24-29, 31-32, 35-41, 43, 45, 49b, 50-52.
7. Caboxylic acids derivatives (3 lectures)
 Naming
 Reactions: Carboxylic acids
 Reactions: Acyl Halides
 Reactions: Acid Anhydrides
 Reactions: Esters
 Reactions: Amides
Sections covered: All of Chapter 21.
Assigned problems: 1-21, 23-25, 28-30, 32-33, 35-41, 43-45, 47-49, 51-53, 56, 63-66, 71.
8. Carbonyl Alpha-Substitution Reactions (3 lectures)
 Keto-Enol
 Mechanism of Alpha-Substitution
 Alpha Substitution: Ketones and Aldehydes
 Alpha Substitution: Carboxylic Acids
 Enolate Preparation
 Enolate Reactions
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Sections covered: All of Chapter 22.
Assigned problems: 1-39, 42-47, 52, 54-56.
9. Carbonyl Condensation (5 lectures)
 Aldol Reaction
 Formation of Enones
 Mixed Aldol Reactions
 Intramolecular Aldol
 Claisen Condensation
 Mixed Claisen
 Intramolecular Claisen: Dieckmann Reaction
 Michael Addition
 Condensation with Enamines: Stork Reaction
 Robinson Annulation
Sections covered: All of Chapter 23.
Assigned problems: 1-46, 50-51, 53-54, 56, 58-63.
10. Benzene and Aromaticity (3 lectures)
 Naming
 Stability of Aromatic Compounds
 Huckel Rule
 Aromatic Compounds: Ions, Heterocycles, Polycycles
Sections covered: All of Chapter 15
Assigned problems: 4-12, 14-17, 24-40, 42.
11. Electrophilic Aromatic Substitution (4 lectures)
 Reactions: Halogenation, Nitration, Sulfonation, Hydroxylation
 Friedel-Crafts Reactions: Alkylation and Acylation
 Substituent effects
 Nucleophilic Aromatic Substitution
 Benzyne
 Oxidation and Reductions of Aromatic Compounds
Sections covered: All Chapter 16
Assigned problems: 17.31d, f, 17.32, 17.52, 18.31, 18.38, 18.53, 18.55, 18.56, 19.4b, c,
19.53, 20.30, 20.42, 20.46-48, 20.49a, 21.42, 21.54, 21.55, 21.57.
Chapter 16: 1-37, 39-56, 60-63, 65, 69-70, 72-75.
12. Amines and Heterocycles (3 lectures)
 Naming
 Basicity
 Preparation
 Reactions
 Heterocycles
Sections covered: All Chapter 24.
Assigned problems: 1-6, 8-20, 22-53, 55-57, 59, 63-64, 66, 68-70, 72.
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13. Pericyclic Reactions (If time allows, 5 lectures)
 Molecular Orbitals
 Electrocyclic reactions
 Cycloaditions
 Sigmatropic Rearrangements
Sections covered: All Chapter 30, sections 14.4, 14.5, 18.4.
Assigned problems: 17.43, 18.10, 18.49.
Chapter 14: 7-10, 17, 18, 21e, 27, 32-41, 43-45, 55-57.
Chapter 30: 1-30, 32, 34-38, 40.
All information on this syllabus is subject to change at the discretion of the instructor.