Organic Chemistry II (Chem UA 226.001)
New York University, Spring 2012
Syllabus
Instructor: Prof. Adam B. Braunschweig
Office: Brown 664, Molecular Design Institute
Email: adamb@nyu.edu
Phone: (212) 998-8495 (x88495)
Office Hours: MW 10-11am; M 5:30-6:30pm
Lecture Location: Cantor 102
Lecture Time: Tues/Thurs 8-9:15a
Recitation Leaders: Dr. Corey Valdez
(cv32@nyu.edu) and Dr. Francesca
Gruppi (fg40@nyu.edu)
Tentative Lecture/ Exam Schedule.
Lecture
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
Date
1/24
1/26
1/31 Quiz
2/2
2/7 Quiz
2/9
2/14 Quiz
2/16
2/21
2/23
2/28 Quiz
3/1
3/6 Quiz
3/8
3/20
3/22
3/27 Quiz
3/29
4/3 Quiz
4/5
4/10 Quiz
4/12
4/17
4/19
4/24 Quiz
4/26
5/1
5/3
TBA
Topic
Dienes and Allyl Systems
Dienes and Allyl Systems
Dienes and Allyl Systems
Conjugation and Aromaticity
Conjugation and Aromaticity
Orbital Symmetry
Orbital Symmetry
Orbital Symmetry
Exam 1
Aromatic Substitution
Aromatic Substitution
Aromatic Subsitution
Carbonyl Chemistry I
Carbonyl Chemistry I
Exam 2
Carboxylic Acids
Carboxylic Acids
Acyl Compounds
Acyl Compounds
Carbony Chemistry II
Carbony Chemistry II
Exam 3
Intramolecular Reactions
Intramolecular Reactions
Carbohydrate Chemistry
Carbohydrate Chemistry
Carbohydrate Chemistry
Final Exam Review
Final Exam
Chapter
12
12
12
13
13
20
20
20
14
14
14
16
16
17
17
18
18
19
19
21
21
22
22
22
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Course Description.
The aim of this course is to introduce you to advanced concepts in organic chemistry. The focus will
be on new organic reactions, mechanisms, and multistep synthetic sequences. Examples of medical
and biological significance will be discussed, and other topics from the primary literature will be
presented.
This course is given concurrently with Section 002 that is taught be Professor Maitland Jones; the
courses are not identical. Students enrolled in Chem UA 226 Section 001 must make sure that they
are attending lectures by Professor Braunschweig and one of the recitation sections instructed by Dr.
Gruppi or Dr. Valdez.
The course information will be disseminated in biweekly lectures. Lecture notes will be provided.
Weekly recitations are available to address specific question. There will be 3 midterm exams, 9
quizzes, and one final examination. The lowest of the three exam grades will be dropped. 33% of the
grade is from the associated laboratory course.
Recitations and Email Policy.
Students enrolled in Lecture 001 should enroll in recitations 109-115 & 117 only. The instructors are
Dr. Gruppi and Dr. Valdez. Recitations will cover the important lecture topics, and the instructors will
work through example problems. All course-related emails should be sent to your recitation instructor.
Emails sent directly to Prof. Braunschweig will not be answered unless forwarded from the recitation
instructor. Questions that they cannot address will be forwarded to Prof. Braunschweig. Emails will be
answered within a 48 hour period, but not on the weekends (your recitation leaders deserve a break
too).
Textbook.
The textbook for the course is Maitland Jones and Steven A. Fleming, Organic Chemistry, Fourth
Edition, W. W. Norton, Publishers, ISBN 0393931498. The following molecular model kit is strongly
suggested and will be allowed on the exams: Maruzen, HGS Stereochemistry Molecular Model 4010
Student Set. Exams will be taken from material covered in class.
Homework.
Homework for this course will not be graded, but suggested homework problems from the textbook
will be posted in class and online. Quiz questions will be taken directly from the homework problems.
Smartwork will not be used.
Grading Policies.
Quizzes. There will be 9 quizzes given approximately every week in recitation on Friday on the weeks
denoted in the lecture schedule. Each quiz will be worth 20 pts. To accommodate people who may
miss quizzes, only the eight highest quiz scores will count towards the final grade. The quiz questions
will come primarily, but not entirely from the suggested homework problems. Other questions will
come from the examples from the primary literature that are discussed in class.
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Exams. There will be three midterm examinations and one final exam. The midterm exams will be
worth 150 pts each, and the final will be worth 200 pts.The midterm exams will be given in class. The
lowest exam grade will be dropped automatically. Because of the cumulative nature of organic
chemistry, the exams will be, by necessity, comprehensive.
Homework. Homework will not be graded but is strongly recommended. Suggested homework
problems will be given in class and posted onto the course Blackboard website.
Lab Grade. This course is paired with a laboratory. The laboratory is 33% of the course grade.
Regrading Policy. Mistakes will be made, and every effort will be made to remedy grading errors. To
submit a regrade, please fill out the regrade form that is available on the course Blackboard website.
Regrades will not be made on any exam or quiz that was written in pencil or on any exam that has
been altered.
Missed Exams. Three midterm exams will be given, and the lowest exam score will not count towards
your final grade. There will not be any make-up exams. There will be no make-up exams for the final
unless you have an official notification from the Dean of undergraduate studies.
Estimated Grade Distibution.
Not including the lab grade, there will be 660 pts available from the exams and quizzes. There is no
grade given for recitation or lecture attendance. Below is the tentative grading scheme, but these
numbers may be adjusted at the end of the course:
Points
660-560
559-480
480-400
399-300
<300
%
(100–85 %)
(84–73%)
(72–53%)
(52–45%)
(<45%)
Grade
A or A–
B+, B, B–
C+, C, C–
D+,D
F
Academic Integrity.
All students should familiarize themselves with NYU’s academic integrity policy that can be found at:
http://www.nyu.edu/about/policies-guidelines-compliance/policies-and-guidelines/academic-integrityfor-students-at-nyu.html
Copying or falsifying exams or quizzes will not be tolerated, all exams must be written in pen, and no
regrades of exams written in pencil will be accepted. Violations of the academic integrity policy will be
reported to the Dean’s Office with all deliberate speed.
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Further Reading.
For many students, this course may be their last formal training in Organic Chemistry but they may
want to independently continue to study this subject. For those students, below is a list of suggested
papers and books that can be used to advance your chemical knowledge.
A good general textbook: Smith, M. B.; March, J. March’s Advanced Organic Chemistry: Reactions,
Mechanisms, and Structure. Wiley Interscience.
For a rigorous treatment of stereochemistry: Eliel, E. L.; Willen, S. H. Stereochemistry of Organic
Compounds. John Wiley & Sons.
A look at some total syntheses: Nicolaou, K. C.; Sorenson, E. J. Classics in Total Synthesis. Wiley
VCH.
More on carbohydrate structure: Stoddart, J. F. Stereochemistry of Carbohydrates. Wiley
Interscience.
An encyclopedic text on the interplay between physical and organic chemistry in research: Anslyn, E.
V.; Dougherty, D. A. Modern Physical Organic Chemistry. University Science Books.
Comprehensive discussion of orbitals and orbital symmetry on reactions: Fleming, I. Frontier Orbitals
and Organic Chemical Reactions. Wiley Interscience.
A practical guide to reactions in the lab: Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A.
R.; Vogel’s Textbook of Practical Organic Chemistry. 5th Ed. Prentice Hall.
Protecting groups and how to use them: Greene, P. G. M.; Wuts, T. W. Greene’s Protective Groups in
Organic Synthesis. Wiley Interscience.
Basically every reaction is listed with references: LaRock, R. C. Comprehensive Organic Synthesis: A
Guide to Functional Group Preparations. Wiley VCH.
Concluding note. The chemical industry is one of the largest industries in the world. Chemistry is also
essential in major product in the medical, energy, and the silicon industries. As instructors of large
courses, the material that we deliver only scratches the surface of the field and cannot
comprehensively describe the depth and breadth of this subject. To really learn organic chemistry
requires a deeper immersion through independent research.
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