CHEMISTRY 234.

02 – ORGANIC CHEMISTRY LAB II

This syllabus is subject to change pending notification verbally or via the email list.
Wednesday(.02), 1:10 – 4:00 pm
Prof’s. Dudley Thomas
Office: Tomsich Hall 015
Office hours: Tues. 10:30 am-12:00 pm and Wed. 4:30-5:30 pm or by appointment
PBX: 5358
email: thomasdg
Texts: Mayo; Pike and Trumper "Microscale Organic Laboratory" 4th edition
Zubrick "The Organic Chem Lab Survival Manual," 6th edition
Required Material: "Organic Chemistry Laboratory Notebook" – Chemical Education Resources, Inc. (CER)
Point Distribution:
7 Data Sets (75 pts each) 525
1 Lab Report with Data Set 200
Final Exam 150
Quizzes (15 points each) 105
Total 980
Goals: Chemistry 234 builds your technical foundation in experimental organic chemistry. This semester will
begin with completion of the seven-step convergent synthesis of hexaphenylbenzene. Your products will need
to be isolated in high purity and yield not only for the product card, but also for use in the next step of the
synthesis in the case of the multi-step synthesis. Careful planning and good experimental technique should
allow you to complete the synthesis using only material you synthesize yourself. A variety of other syntheses
will then be performed to further enhance your experimental aptitude.
Attendance: Organic chemistry continually builds upon itself, and it is quite easy to get behind if you miss a
particular lab period. Also, the labs are often quite full. Therefore, attendance to your assigned laboratory
section is mandatory. Once lab sections are finalized, you may not switch lab sections during the semester. If
you miss lab due to an excused absence such as a family or medical emergency or scheduled sporting event, you
must obtain permission from your instructor and the instructor of the other section to attend an alternate lab
section.
Course Meeting Time: We will meet in Tomsich 207 at 1:10 pm for a 20 – 30 minute pre-lab lecture during the
first week of a particular experiment. The lab will begin with a 10 minute quiz germane to the experiment at
hand (see below). The quiz always ends at 1:20 pm sharp and if you are not present for the quiz, you will
receive no credit. You will have only your laboratory notebook to help you during the quiz, so you should make
relevant notes therein. It is vital that these notes be clearly separate from what you write during lab. Planning
your lab work ahead of time will increase your efficiency in lab. Following recitation, laboratory work will
commence in Tomsich 209. If we are in the second week of an experiment, you may begin working promptly at
1:10 pm in Tomsich 209 EXCEPT in the case of the first experiment. The first quiz will be held prior to
beginning the second week of work on this experiment. You should confine your lab work to the scheduled
hours. No extra time will be given if you are unable to complete an experiment due to a clear lack of pre-lab
preparation or a lack of focus or efficiency during lab.
Analysis Party: The lab will be open Sunday, Tuesday and Thursday (exact hours to be announced in class)
nights during the Math Science Skills Center from 7 – 9 pm and will be staffed by one of the lab proctors.
During this time you may perform analytical techniques such as melting point analysis and the various
spectroscopies. No other experiments may be performed. As a guideline, if all you had was your sample and
sample prep material, you can not do anything which would require opening your drawer.
Safety: The safety rules for the course are stated in Mayo, Chapter 2 and in Zubrick, Chapter 1. The most
important rules are: 1) Wear safety goggles at all times – being in the lab without goggles will cost you 5 points
per incident. However, if you find an instructor in any lab without goggles, you are entitled to 10 points, 2)
Long pants and shoes that cover the entire foot must be worn at all times, 3) No eating or drinking (This
includes gum) and 4) Be mentally alert to hazards and prepared for emergencies. If you are uncertain whether
something is safe, consult with me or the laboratory assistant.
Reading: The location of an experiment in your laboratory text is listed on your schedule. At the beginning of
each experiment Prior Reading is listed. I will assume you have read this material as well as any relevant
discussions and introductions, even if they do not immediately precede the experiment in question.
Laboratory Notebooks: You are required to purchase and maintain a laboratory notebook; if you have one from
the previous semester with many remaining pages, you may use it. Learning to keep an accurate and detailed lab
notebook is critical as it is often your only source of information to help you remember what you actually did in
lab when writing a lab report, trying to interpret spectra, etc. The notebook for this course contains white pages
for your original record of work and yellow pages which are copies of the white pages. Although there is no
single correct way to keep a notebook, for this course you must precisely follow the sample given on the course
webpage. I will check your notebooks before the end of lab each day and they will be graded again in detail
when handed in. The most important rules are: 1) Your lab notebook is your scratch paper – observations, data
and calculations should be recorded directly into your notebook at the time the observations or measurements
are made, 2) You should write with indelible ink and 3) After you are finished with your experiment, your lab
notebook should contain sufficient information for another investigator, familiar with the field, to be able to
reproduce your work, using only your notebook as a guide. Other useful references can be found in Mayo, pp.
30-32 or in Zubrick, Chapter 2.
Data Sets: At the completion of each experiment, you will prepare a data set to be graded. Data sets are your
proof that you have completed the experiment and will be the primary basis of your grade. The due dates for
each data set are indicated on the schedule of experiments. Each data set will include the following items:
1. Product Card -- A product card is a summary card of the data collected and should be stapled to the front of
your data set. Fill out all pertinent sections of the card and in the remarks section indicate the attachments that
are stapled to the card (e.g. -- 'Included with this card: experimental section, 1H NMR spectrum, 13C
NMR spectrum, IR spectrum, product vial, and lab notebook pages’)
2. Experimental Section -- For each experiment you should write an experimental section in prose suitable for
publication in an ACS organic chemistry journal (example experimental sections are linked to the course
webpage). General guidelines for scientific writing should be followed. For a review of these guidelines refer
to A Brief Guide to Writing in Chemistry (linked to the course webpage).
3. Annotated Analytical Data -- All analytical data you turn in should be interpreted and clearly annotated.
Annotation includes carefully drawing the structure of the compound under analysis and clearly correlating
spectral signals with that structure. Examples of annotated spectra are linked to the course webpage. All
spectra should have the following information on them: compound structure, compound name, compound ID
number (I-JEH-017, lab book number - initials - page) and method of sample preparation (i.e. KBr pellet, thin
film, CDCl3, etc). For IR spectra, only major features need to be labeled. For NMR spectra, every peak must be
accounted for.
4. Labeled Vial Containing your Product -- Place your product material into a sample vial and label the vial
with the compound name, compound ID number, and your name. The vial can be taped to the back of your
product card.
5. Carbon Copies of Pertinent Lab Book Pages -- After you have finished your notebook entry for a given
experiment, tear out the carbon copies and turn them in with the data set.
Laboratory Report: A combined lab report for experiments [A3a] and [A4ab] (approximately 3-6 typewritten
pages, excluding attached data sets) will be written by each student this semester.
The report is to be typewritten and should include the following sections: Abstract, Introduction, Results and
Discussion, Sample Calculations, Experimental, Questions, and References. You must also attach the Data Set
for both experiments as an appendix to the report which will graded. All structures must be drawn using
ChemDraw which is available on publicly accessible computers in Fischman 009 or as a free download
(http://sitelicense.cambridgesoft.com/sitelicense.cfm?sid=1861) Chemical structures which are scanned, hand-
drawn, copied from the web, etc. are not acceptable.

Please refer to A Brief Guide to Writing in Chemistry for guidance in writing your report. A brief description of
expectations for each section are included below:

Abstract: This is a summary of your results and the methods used to obtain them. It varies from 1-5 sentences,
but never exceeds 110 words (approximately 8 lines).
Introduction: This is a statement describing the purpose and goals of the experiment. You should describe (in
words, pictures, balanced chemical equations, mathematical equations, etc.) the new method(s) and/or chemical
reaction(s) that you have investigated for this report.
Results and Discussion: This includes your data (results) and the interpretation/explanation of your data
(discussion). Your data are most effectively presented using tables, graphs, lists, etc. (spectral data should be
included as appendices that are referenced in the text). You should interpret and discuss your data in terms of
what you learned from them, and how the data reinforce or contradict the principles taught in this course and in
Chemistry 231/2 (Organic lecture). Typically, this is the main body of text in your report.
Sample Calculations: This contains a detailed account of how you arrived at a certain number or result during a
calculation. You should show one sample calculation for each type calculation (i.e. one each for % recovery,
theoretical yield, % yield, optical rotation, etc.) that you performed for a particular experiment. As always, pay
attention to significant figures.
Experimental: This is a description of what you actually did in the laboratory according to your notebook and
not necessarily what is described in Mayo. The experimental is written in the third person, the past tense, and in
the passive voice. Example experimental sections are given on the course webpage.

References: Sources of information that were used in the report (Mayo et. al., Zubrick, CRC Handbook of
Chemistry and Physics, Science, Journal of Organic Chemistry, etc.). This is an important and often overlooked
section of a lab report. Please format references as endnotes in the ACS style
(http://pubs.acs.org/books/references.shtml).

Quizzes: A 10-minute quiz will be given at the beginning of each experiment (on the first week of two-week
experiments with the exception of the first week as described above). The content of the quiz will be germane to
the experiment at hand and may include questions about technique as discussed in Zubrick, questions assigned
about the experiment at hand in Mayo (see lab schedule), spectral interpretation questions, questions related to
material that should be written in your lab book in preparation for the experiment, or questions concerning
concepts related to those in the experiment at hand. One question may require application of known material to
solve a similar problem.

Grading: Your performance will be evaluated over the entire semester based upon the following scale: 97% -->
A+; 93% --> A; 90% --> A-; 87% --> B+; 83% --> B; 80% --> B-; 77% --> C+; 73% --> C; 70% --> C-; 67% --
> D+; 63% --> D; 60% --> D-; <60% --> F. The instructors reserve the right to alter the scale at the completion
of semester; however, the scale will be no harder than that listed above.
Academic Honesty: You are expected to follow the college policy for academic honesty (Kenyon College
Course of Study 2009-2010, pp 24 – 279). All materials submitted for credit must be your own work. The
complete policy is available for download (http://documents.kenyon.edu/courses/2009_2010/honesty.pdf).
Final Exam: The final will be cumulative for the semester. You may use your laboratory notebook but will
not be allowed to use a calculator. Two sessions – May 11, 8:30 am & May 11, 1:30 pm are available in which
you may take the exam. You may attend either but must sign up for a session earlier in the semester.
Section 504 of the Rehabilitation Act of 1973 and the Americans with Disabilities Act of 1990: If you have a
disability and need accommodation in order to fully participate in this class, please identify yourself to Erin
Salva, Coordinator of Disability Services (PBX 5145, [email protected]). All information and documentation
of disability is confidential. No accommodations of any kind will be given in this course without notification
from the Coordinator of Disability Services.

Withdraw Late: Co-requisite for this course is CHEM 232. However, withdrawing late (WL) from this lab
course does not involve also withdrawing from the associated lecture course – they are separate courses with
separate grades.

Equipment Loss or Breakage: There are no up-front chemistry lab fees; however, at the beginning of each year,
you will need to sign a check-in sheet stating that you are accepting financial responsibility for any breakage or
loss of lab drawer contents. Your student account will be assessed charges for lost or broken items at the end of
the year.