CHEMISTRY 51

Organic Chemistry
Fall 2014
Professor Clay Bennett Lecture: Room P-104
Pearson 305A Tue, Fri 12:00 1:15
Office Hours: Tue, 1:20-2:20; Wed, 1:15-2:15; Fri, 1:20-2:20 designated: Block F+(TF)
or by appointment
Telephone: 617-627-0621 CHEM-51 Web Site:
e-mail: clay.bennett@tufts.edu https://trunk.tufts.edu

Students enrolled in CHEM 51 must have credit for CHEM 2 or the equivalent.

Required Text:
David Klein Organic Chemistry, 2
nd
Edition, ISBN: 9781118452288
David Klein Organic Chemistry Student Study Guide and Solutions Manuel, 2
nd
ed. ISBN: 9781118647950
(Note: if you have the 1
st
edition of Klein that will be fine. The difference is the assigned problems). These will be
made available in the front office the week that we cover this topic).
Study Aids:
Molecular Visions molecular model kit #1B, from Darling Models ISBN: 9780964883734

Recommended Supplements:
David Klein Organic Chemistry as a Second Language, First Semester Topics ISBN: 978-1-118-01040-2

Grading Policy
Relative Weight
Exam 1 18
Exam 2 18
Exam 3 18
Final Exam 36
Recitation, Quizzes, Problem Sets 10
______________
Total 100

Grades.
The total number of points in the course equals 1000. These will be split up between quizzes (100 points), 3 mid
term exams (180*3 = 540 points) and one final exam (360 points).
Relative Weights: Every exam will have two types of scores (RAW and SCALED). The RAW score is simply the
number of points that you score on a particular exam, while the scaled score is your performance relative to that of
your classmates. In the usual circumstance, the average score will be scaled to the C+/B limit.
The RAW score of any quiz will be counted without conversion (quizzes will be given in class -total of 5). The
bottom two scores in the quizzes will be dropped and the rest averaged. If you miss a quiz, a 0 will be recorded and
considered your score for that quiz.
The exact conversion scheme (for the scaled score) will be announced after each exam, so that you are aware of
how you are doing at any time during the course. The final score is the sum of all points/scores. The final grade
will be assigned according to the table given below. The final grade will be based on recitation, problem sets,
quizzes and exams. No extra credit projects will be assigned or accepted.

Final Course Grade Final Score (% max score)
A+ 967-1000 (97-100)
A 933-966 (93-97)
A- 900-932 (90-93)
B+ 876-899 (87-90)
B 833-866 (83-87)
B- 800-832 (80-83)
C+ 767-799 (77-80)
C 733-766 (73-77)
C- 700-732 (70-73)
D+ 667-699 (67-70)
D 633-666 (63-67)
D- 600-632 (60-63)
F <600 (<60)

**************
Here is an example of how you can calculate your "current grade" after two exams and three of the five quizzes:
3 quizzes (out of 5): 46 points (out of 60): at the end of the semester, bottom two scores will be dropped
Exam I: 100 points (scaled to 141)
Exam II: 112 points (scaled to 155)
Maximum number of points possible at this time: TOTAL = 420
60 (Quizzes) + 180 (Exam I) + 180 (Exam II)
Earned by you: YOUR TOTAL SCORE = 342
46 (Quizzes) + 141 (Exam 1) + 155 (Exam II)
GRADE = (342/420)*100 = 81.4 % of the Maximum Score
"B-" is your current grade.

**************
CAUTIONARY NOTE: It is assumed all students are aware of the ACADEMIC INTEGRITY code at Tufts.
Violation of this code by use of materials not directly authorized by the instructor during exams and quizzes will
have serious implications. Please consult http://uss.tufts.edu/studentaffairs/policies/campus/academicintegrity.asp
for detailed information.
Do NOT engage in behavior that gives the appearance of cheating, such as passing notes, whispering, or looking in
the direction of another students work. Do NOT bring your cell phone, tablet, music device, programmable
calculator or any other electronic device to an exam. If an exam proctor sees you handling an electronic device
(even to silence a phone if it rings or vibrates in the middle of the exam), the Judicial Affairs Officer will treat it as
an academic integrity violation. DO turn off your cell phone and put it out of reach and out of sight before the
exam begins!
Regrades. Only exams written in ink will be accepted for regrades. Concisely state your written request for the
regrade and it will be considered carefully. All regrade requests must be received in my mailbox within 24 hours
after the graded examination is returned to you. I will not accept regrade requests made in any other fashion,
including requests made during office hours or via email. Please note that your entire exam will be regarded,
and grades may go up or down as a result. All regrades are final.

Make-up Exams. If you miss an exam, you must contact the course instructor within 24 hours of the exam.
Missed examinations may be made up only after submission of a valid written excuse. For cases involving illness,
you must submit appropriate medical documentation confirming that you were treated by a health professional
during the illness before a make-up exam will be granted. For all other instances the only acceptable excuse note
will be one from the Office of the Dean of Students. The note must stipulate the days for which the excuse is valid
and must state explicitly that, in the opinion of the Dean, the reason for missing the exam warrants a make-up exam
without penalty. Otherwise, a score of 0 will be given for the exam. University policy on absences may be found
at:
http://ase.tufts.edu/healthservice/servicesClassAbsence.htm

Special needs:
Anyone with special needs that may require some modification of seating, testing, or any other course requirements
should contact the Academic Resource Center at (617) 627-4345 or email at: disability.services@ase.tufts.edu or
stop by Dowling Hall, Room 720. You must provide me with a letter for any special needs for exams and quizzes.
Letters must be obtained from Student Accessibility Services (http://uss.tufts.edu/arc/disability/). Please note if
you require extra time I will have to reserve a room in the department for you to finish. I will therefore need at
least 24 hours notice in order to implement this. It is recommended that if you have special needs please make
arrangements as soon as possible (rooms in the department fill up quickly).
Study. Plan on a minimum of 4 hours of study and problem solving outside of class for every lecture. For most
people, a minimum of 80 minutes a day, six days a week or two hours a day, four days a week should work well.

Recitations. Superb recitation instructors provide weekly Chem 51 recitation sections, scheduled on Monday,
Tuesday, Wednesday, Thursday and Friday. Recitations begin Tuesday, September 2, 2014.

Problem Sets. Problem sets will be assigned at the beginning of each section on Trunk. Hand in your written
answers to assigned problems at the specified times.

Teaching Assistant Office Hours. If you would like to ask a question or discuss topics or problems with a
Teaching Assistant, there are scheduled hours for Chem 51, in Pearson Annex Room 004x.

Trunk Course Site. Course information can be found at the following address:

http://trunk.tufts/edu

Login and then click on FA14-CHEM0051-01-Organic Chemistry

This site includes the course syllabus, class schedule, exam dates, announcements, staff information, lecture
handouts, problem assignments, TA office hours, recitation times and selected external links.

Review Sessions. A day or two before each exam, a review session is scheduled in P-104 at noon (September 29,
October 27, and December 2014). Practice exams will be provided in advance online. Write a complete answer
for each practice exam problem before coming to the review session. Be prepared to present and explain one or
more of your answers at the blackboard during the review session. Be prepared to comment upon and discuss
answers presented by others. Active participants gain the most benefit from these review sessions.

Library Resources. On reserve for this course at Tisch Library are two other organic chemistry texts along with
their Study Guides. They are available for your use:

Maitland Jones, Organic Chemistry, Third Edition, 2005.

Maitland Jones, Jr. Study Guide/Solutions Manual to Organic Chemistry, Third Edition 2005

Andrew Streitwieser, Clayton Heathcock, and Edward Kosower, Introduction to Organic Chemistry,
Fourth Edition, 1992.

Andrew Streitwieser, Clayton Heathcock, and Edward Kosower Study Guide and Solutions Manual
to Introduction to Organic Chemistry, 4Fourth Edition, 1992.

T.W. Graham Solomons and Craig B. Fryhle Organic Chemistry, 11
th
Edition, 2014.

T.W. Graham Solomons and Craig B. Fryhle Study guide and solutions manual to accompany
Organic chemistry 11
th
Edition, 2014.

The authors of these texts present the material of the course from a somewhat different point of view. When you
have mastered a topic in our text and wish to examine that topic in greater depth, one of these texts may be helpful.

Tutors. The Academic Resource Center may provide a tutor for you if necessary. However, the number of tutors
available is limited.

























Date Notes Lecture Subject Readings
9/2 1 Review and Introduction Klein 1 and 2
9/5 2 Acidity Klein 3
9/9 3 Alkanes, cycloalkanes, conformation Klein 4
9/12 4 Stereoisomerism Klein 5
9/16 Quiz 1 5 Chemical Reactivity and Mechanisms Klein 6
9/19 6 Substitution Reactions Klein 7.1-7.5
9/23 7 Substitution Reactions (cont.) Klein 7.6-7.9
9/26 Quiz 2 8 Alkenes and Elimination Klein 8.1- 8.11
9/30 EXAM 1 (Lectures 1-7)
10/3 9 Alkenes and Elimination (Cont.)
Addition to Alkenes
Klein 8.12-8.14
9.1-9.9
10/7
Drop date
10 Additions to Alkenes Klein 9
10/10 Quiz 3 11 Alkynes Klein 10
10/14 12 Alcohols Preparation Klein 13.1-13.6
10/17 13 Alcohols - Reactions Klein 13.7 13.10
10/21 Quiz 4 14 Ethers, Epoxides, Thiols Klein 14
10/24 15 IR spectroscopy, mass spectrometry Klein 15.1-15.10,
15.13 to 15.16
10/28 EXAM 2 (Lectures 8 to 15)
10/31 16 NMR Spectroscopy Klein 16
11/4 17 Aldehydes and Ketones Klein 20.1-20.8
11/7 18 Aldehydes and Ketones Klein 20.9-20.13
11/11 Veterans Day No Class
11/14 19 Carboxylic Acids Klein 21.1-21.6
11/18 20 Carboxylic Acids Klein 21.7-21.15
11/21 Quiz 5 21 Enols and Enolates Klein 22.1-22.4
11/25 22 Enols and enolates Klein 22.5-22.7
11/28 Thanksgiving Holiday-No Class
12/2 EXAM 3 (Lectures 16-22)
12/5 23 Amines Klein 23.1-23.7,
23.9, 23.12
12/16 FINAL EXAM (Cumulative)
















Department of Chemistry Undergraduate Majors

Educational Goals and Required Knowledge and Skills

General education goals in chemistry:

1. Communication. The ability to write, display information, and orally communicate in a scientific format.
2. Primary literature. The ability to search for, read and understand primary sources of scientific literature.
3. Understanding data. The ability to understand chemistry data, how it is produced, and how it is applied.
4. Quantitative analysis. The ability to apply quantitative measurement and analytical laboratory techniques to
scientific problems.
5. Mathematical tools. The ability to apply mathematical tools to chemistry problems that often involve multiple
variables, statistics, and symmetry.
6. Scientific method. The ability to develop a hypothesis, design experiments to test that hypothesis, execute
experiments, interpret data, and refine a hypothesis in light of new data.
7. Chemistry as the central and molecular science. Understanding how chemists solve problems across
disciplines by designing, synthesizing, and analyzing molecules with defined structure and function.
8. Critical evaluation. The ability to critique scientific claims in the technical and popular press with respect to
accuracy, interpretation, and application.
9. Integrity. The development of honesty, responsibility, and integrity with respect to the generation and
interpretation of data as a scientist and as a citizen.
10. Science and society. The development of a sense of responsibility for promoting education, diversity and
functional literacy in science within the larger community.


Knowledge and skills requirements:

1. Problem-solving skills, including logical reasoning, diligence, and attention to quality, consistency, and
thoughtfulness in ones work
2. Structure. Three-dimensional molecular structure and chemical bonding and their origins in the electronic
structure of matter
3. Properties and reactivities of important chemical classes, and their uses and preparation
4. Energy and thermodynamics
5. Chemical equilibria including acids, bases and solubility
6. Chemical reactions, stoichiometry and mechanisms
7. Reaction kinetics
8. Oxidation, reduction, and electron transport
9. Chemical basis of biological function
10. Experimental techniques. Knowledge of, and safe practices in, analytical and preparatory laboratory
techniques, including synthesis of molecules and/or materials
11. Hands-on laboratory experience
Department of Chemistry Undergraduate Majors

Learning Goals and Skills and Competencies

The Chemistry Department has identified a set of learning goals and a list of skills and competencies we expect of
our graduating majors. The list appears in full on our departments website, http://chem.tufts.edu

While each individual course in our curriculum may not address all items on the lists, completion of all required
courses leading to the major will. The grid below indicates which of the goals, skills, and competencies will be
addressed in this course. Entries of 1, 2, or 3 indicate that the topic will be a primary, secondary, or tertiary
focus of the course.

Course: Chem51
Semester: Fall 2014

Learning Goals
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