Chemistry 030-205-03 Syllabus

Organic Chemistry

Fall 2014
Lectures: Monday, Wednesday, Friday 9:00-9:50 AM, Remsen 101
Conference Thursday 9-10:20 AM (various locations)
Lecturer: Prof. Chris Falzone
Office: 314 Chemistry Building
E-mail: [email protected]
Office Hours: Monday and Wednesday 3 – 4:30 PM or by appointment
Text, Molecular Model, and iClicker:
 P. Bruice, Organic Chemistry, 7th ed. with solutions manual; a molecular model kit is strongly recommended
An iClicker unit is a remote control that is used for in-class voting (see: http://www.cer.jhu.edu/clickers.html)
Problems
You will work problems during your recitation session but mostly, you will work them on your own. Specific
homework assignments for grade will not be made. Working the problems within the chapter and at the end of the chapter is
one of the best methods to learn the material and prepare for the exams. It is anticipated that you will be able to solve all the
problems. The problems that develop the necessary basic skills and those that are particularly indicative of what to expect on
the exams are listed at the end of the syllabus as "Suggested Problems." You are expected to do all of the problems within
the chapter.

Course Content
For the purpose of exams, the course content is defined by (a) the lectures, (b) the relevant chapters in the text, and (c)
any other specific assignments that are made. The outline and order of the topics covered is presented at the end of this
handout. Please note that not all chapters will be covered in the order they are in the book. Some sections have been omitted
and some will be covered at a later time. The sections that have been excluded will not be covered in the lectures, and the
material will not be a part of the exams.
Grades
Your course grade is based on the following criteria:
 Three comprehensive exams, 100, 100, 100 points
 Comprehensive final exam, 150 points*
 Conference Quizzes, 70 points**
 Lecture attendance#
Final grades are based on performance on exams and quizzes. There are no set grade lines and it is important to note that
there is no set percentage of a certain grade. In fact, the entire class can get an “A”. After each exam, you will receive some
feedback as to how your numerical scores might translate into class grades. It is provided only to help you evaluate your own
efforts and scores in the course. These indications should be treated as rough estimates of your final grade. Grade-lines have
to be drawn somewhere, and the unavoidable consequence is that some students are just "a point" away from a higher grade.
For the reason of fairness, the policy in this course is to NOT adjust students' grades in such circumstances.

*The final exam is based on 150 points. The first 100 points of the exam may be used to replace ONE of your midterm
scores if it is higher.

**There will be 10 quizzes and the three lowest are dropped.

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 #
If your attendance is above 85% based on iClicker reports, you will receive 8 points. For 75% attendance, you will
receive a 4 point “boost”. No excuses will be accepted as these attendance levels are lenient. That is, no excuse for dead
batteries, forgotten remote, bathroom breaks. Attendance will be recorded after the first three lectures and you have one week
to clear up discrepancies in the voting. These are bonus points and given at my discretion.

Exams
 1st exam Thursday, October 2, 2014 (9:00-10:20 AM)
 2nd exam Thursday, October 23, 2014 (9:00-10:20 AM)
 3rd exam Thursday, November 13, 2014 (9:00- 10:20 AM)
 Final exam: Saturday, December 13, 2014 (2-5 PM)
 Makeup exam: Tuesday, December 9, 2014 (10 AM-12 PM); Last day of Reading Period
The exam locations will be announced in class.

All exams will be cumulative (but they will emphasize the material covered since the previous test). They will be
constructed in such a way as to emphasize active understanding of the material. To take the exam, you will need a pen or a
pencil. You cannot use books, scratch paper (other than furnished), calculators, cell phones, or electronic devices of any kind
including those not yet invented. You may, however, use a molecular model kit (it may not contain any written materials). If
an exam is missed, it will be replaced with a comprehensive exam that will be administered during reading period. A valid
excuse which requires written justification from an appropriate official such as a non-parent physician or the Dean of Student
Life is required. You should never take an exam if you are sick or otherwise compromised. However, the grade for an
unexcused exam will be a zero.

Regrades
Your examinations are marked according to an explicit key and set of guidelines provided by the Professor to the TAs.
If you think that a question has been graded incorrectly, submit the exam to your TA.
In rare instances, an addition error of points may be made; please check for these at once and report any such to the TA
immediately and turn in the exam.
The assignment of points and partial credit is to be considered accurate; the score you receive is not an “opening bid” in some
putative haggling process. NEVER bring such issues to the Professor. In extraordinary circumstances only, a “regrade” may
be entertained, subject to the following regulations:
1. The request for regrade must be submitted to your TA by the end of conference when the exam is returned, and must be
accompanied with a written explanation of the problem. (“I think I deserved more points” is a non-starter.)
2. The entire exam will be regraded--this may result in no change, or a lower or a higher score. NOTE: All exams are
scanned.
Advice: The neater and more orderly your exam, the more likely you are to receive full marks. When TAs have to hunt about
for your answer, or decipher squiggles and jots, or cast about to guess at your manner of proceeding, it is more likely that the
credit you receive will be lower than you might like. Therefore, fill out exam papers in an orderly and straightforward way
with clear, to-the-point explanations. Practice this method of answering when writing out your homework exercises. You are
encouraged to discuss chemistry and/or the course with your teaching assistant and your instructor Simple questions or
comments can also be sent via e-mail. For administrative questions, see your teaching assistant.
Rules for Class Periods, Exams, and General Considerations
Organic Chemistry is a difficult course. It covers a lot of demanding material. As such, you should pay attention during
lecture. Therefore, no electronic devices are to be used in the class, during exams, or during conference. Observations
made over the past few years suggest some generally useful strategies that help to improve student performance. These are
summarized below, and a more extensive discussion is provided on the web.

 read the chapter material before the lecture

 study everyday; do reviews weekly
 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

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  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) the 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
Academic Ethics
Cheating is wrong. Cheating hurts our community by undermining academic integrity, creating mistrust, and fostering unfair
competition. The university will punish cheaters with failure on an assignment, failure in a course, permanent transcript
notation, suspension, or expulsion. Offenses may be reported to medical, law, or other professional or graduate schools when
a cheater applies.

Violations can include cheating on exams, plagiarism, reuse of assignments without permission, improper use of the internet
and electronic devices, unauthorized collaboration, alteration of graded assignments, forgery and falsification, lying,
facilitating academic dishonesty, and unfair competition. Ignorance of these rules is not an excuse. Such infractions are
considered cause, at the least, for awarding a "0" on the exam in question with additional sanctions that are listed above.

Working together before the exam is desired but you must complete all exams on your own. You may not have someone else
take the exams for you. You may not obtain information from another student or provide information to a student about the
exam either by communicating with them or looking at anything that another student has written. You may not allow another
student to see anything that you have written.

On every exam, you will sign the following pledge: “I agree to complete this exam without unauthorized assistance from any
person, materials, or device. [Signed and dated]” For more information, see the guide on “Academic Ethics for
Undergraduates”: http://portalcontent.johnshopkins.edu/sebin/g/u/Johns%20Hopkins%20Ethics%20Guide.pdf
Getting Help
There are a number of mechanisms for you to get help. One of the teaching assistants will be available on Wednesdays the
week before and the week of each of the three exams in 233 Remsen starting at 6 PM. Review sessions will also be held on
the Tuesday before exams. In addition, the following services are available:
Pilot Groups. Join a PILOT group (a peer facilitated problem solving group). PILOT LINK:
http://academicsupport.jhu.edu/pilot-learning/registration/
Small Group Tutoring. The Learning Den is in Gilman Hall. Sign up online at http://tutoring.jhu.edu (Your User ID and
password is your 6-character Hopkins ID (not JHED ID); the two fields are identical)
Sundays - Thursdays, 6 pm - 10 pm. Visit the web site for more information:
http://jhu.edu/academic-assistance/tutoring.html.
410-516-8216, [email protected]
Study Consulting. 385 Garland Hall Suite 3A
http://jhu.edu/academic-assistance/studyconsulting.html
410-516-5506, [email protected]
Classroom Participation via iClicker
To make lectures more interactive, we will use a classroom participation system for in-class voting. The response units that
enable you to participate are available from the JHU Barnes and Noble. Your iClicker must be registered in BlackBoard in
order to keep track of the voting. Questions? Go to: http://www.cer.jhu.edu/clickers.html

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 Chemistry 030.205.03: Outlines of Lectures
1. Structure, Bonding & Molecular Properties (5 lectures*)
 Structure of atoms, atomic orbitals
 Chemical Bonding (ionic bonds, covalent bonds)
 Valence-bond theory (hybridization)
 Molecular Orbital (MO) theory (HOMO and LUMO)
 Resonance
 Electronegativity, dipole moments
 Acids and bases
Sections covered: 1.1 - 1.16; 2.1-2.12
Suggested problems: 1.46-1.73, 2.47-2.70

2. Alkanes (3 lectures *)
 Alkanes as building blocks (constitutional isomers)
 Functional groups
 Nomenclature
 Conformational analysis of alkanes and cycloalkanes (strain)
Sections covered: 3.1-3.15
Suggested problems: 3.52-3.58, 3.61-3.63, 3.65- 3.76, 3.78-3.79, 3.82-3.86
3. Stereochemistry (3 lectures*)
 Optical activity – enantiomers (asymmetric centers)
 Diastereomers, meso compounds,
 R, S Nomenclature, absolute configuration
 Fischer projections
 Chiral molecules without asymmetric centers
Sections covered: 4.1-4.16
Suggested problems: 4.53-4.67, 4.69-4.87

4. Alkenes, Overview of Organic Reaction Mechanisms, and the Addition of HX (3 lectures*)

 Cis-trans (E, Z) isomerism and degrees of unsaturation, nomenclature, structure
 Nucleophilic substitution on methyl halides, Radical chlorination of methane, Addition of HBr to ethylene
 Thermodynamics, kinetics, energy diagrams , transition states, rate-determining step
 Writing reaction mechanisms
 Hammond postulate
Sections covered: 5.1-5.12
Suggested problems: 5.37-5.39, 5.41, 5.42, 5.44-5.50, 5.52-5.58

5. Electrophilic Addition to π Bonds (5 lectures*)

 Hyperconjugation and regioselectivity (Markovnikov’s rule)
 Addition of X2 and HX to  bonds in alkenes, alkynes and dienes
 Carbocations and their rearrangements
 Preparation (mechanistic details are covered under section 8)
 Addition of halogens and water
 Hydration of the double bond
 Epoxide formation
 Catalytic Hydrogenation
Sections covered: 6.1-6.18
Suggested problems: 6.59-6.95, 6.98-6.107

6. The Reactions of Alkynes; Organic Synthesis (2 lectures*)

 Structure and Nomenclature

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  Reactions of alkynes: addition of hydrogen halides, halogens, hydrogen
 Hydroboration-oxidation and mercuric ion catalyzed addition of water
 The acidity of terminal alkynes, acetylide ions, and synthesis of organic molecules
Sections covered: 7.1-7.12
Suggested problems: 7.27-7.37, 7.40-7.57

7. Conjugated Dienes and Aromaticity, (4 lectures*)

 Delocalization of Electrons (Resonance Structures)
 Benzene and Hückel’s Rule
 Aromaticity and Antiaromaticity
 Electrophilic additions of dienes
 Kinetic vs. thermodynamic control
 UV and visible spectroscopy, conjugation, and the chemistry of vision
 Diels-Alder Reaction
Sections covered: 8.1-8.21
Suggested problems: 8.57-8.108

8. The Chemistry of Benzene: Aromatic Substitution Reactions (2 lectures*)

 Halogenation, nitration, sulphonation, alkylation, acyclation
 Reactivity of the aromatic ring (substituent effects)
 Oxidations, reductions of aromatic compounds; reactions of side chains groups
Sections covered: 19.1-19.9, 19.11-1920
Suggested problems: 19.48, 19.50-19.54, 19.56-19.60 (ignore b and e), 19.62, 19.64-19.66, 19.69-19.70, 19.73, 19.73, 19.77, 19.83,
19.88

9. Structure Determination—part 1 (3 lectures*)

 UV spectroscopy (review)
 Nuclear Magnetic Resonance (1H, 13C)
Sections covered: 15.1-14.24
Suggested problems: 15.46-15.78 (do not worry about IR, MS parts)

10. Nucleophilic Substitutions and Eliminations (5 lectures*)

 SN1 and SN2
 E1 and E2; E1cb
 Effects of solvent, substrate structure, and nucleophile (base) on reactivity
Sections covered: 9.1-9.9, 10.1-10.10, 11.1-11.12 (as time allows)
Suggested problems: 9.35-9.68; 10.35-10.63; 11.48-11.70, 11.72, 11.76-11.78, 11.82, 11.84, 11.89

11. Radical Reactions (3 lectures*)

 Substitution reactions of alkanes
 Radical Halogenation: Reactivity-Selectivity Principle
 Radical addition to alkenes
 Allylic bromination
Sections covered: 13.1-13.12
Suggested problems: 13.25-13.48
______________________________________________________________________________
*The number of lectures is approximate; adjustments may be made as necessary. All in-chapter problems should be worked out.