Syllabus

Chemistry 6BL Winter 2014 UCSB

Instructor:
e-mail:

Dr. Morgan Gainer

gainer@chem.ucsb.edu Yes/no questions or requests for appointment only please.
For more in-depth questions please see me in person during my office hours or by
appointment.
Office:
PSBN 3649A
Office Hours: W 12:00-1:00pm
Phone:
805-893-7485
COURSE DESCRIPTION
The purpose of the Chem 6 series is for students to learn the techniques and principles
used in an organic chemistry laboratory and to introduce students to modern spectroscopy. It is,
in part, a practical application of many of the concepts learned in the Chem 109 lecture series. In
Chem 6BL, you will be provided with more opportunities to put into practice the laboratory
techniques learned in Chem 6AL. You will be given further experiences with infrared
spectroscopy, nuclear magnetic spectroscopy, and mass spectrometry.
REQUIRED TEXT AND MATERIALS
Organic Chemistry Laboratory Manual and Techniques
Composition Notebook: Perforated Carbonless
Chem 6BL Course Reader (this contains all spectra that will be used during the quarter)
Knee length lab coat (available at bookstore)
Organic Chemistry, 7th edition by P. Y. Bruice. (Volume 2) RECOMMENDED
IMPORTANT DATES
Week of Jan 5: No Class on Day 1 of Lab
Week of Jan 19: No Class on Day 1 of Lab
Week of Feb 16: No Class on Day 1 of Lab
Week of Mar 9: No Class on Day 2 of Lab
Final Exam: Saturday, Mar 14, 4:00-6:30pm.
TEACHING ASSISTANTS
Your lab TA is an excellent resource for in-lab questions. They will provide instructions
at the beginning of each lab period. Additionally they will hold office hours weekly. A schedule
of all lab TAs office hours will be posted as soon as it is available. You are welcome to ask any
TA for help, but be aware the questions regarding grading should be brought to your specific TA.
LAB ATTIRE AND SAFETY

The safety of all students is a top priority. Because of this, full length pants (no tights)
and close toe shoes are required at all laboratory sessions. If you come to lab wearing
inappropriate clothing you will be sent home. You should change clothes and return as quickly as
possible. Safety goggles and gloves will be provided for you.
Lab work should only happen when the TA is in the lab class. If you arrive early to lab,
patiently wait outside the room until your TA arrives. General lab areas (balances, hoods, etc.)
should be kept clean and organized. Failure of a section to maintain general areas clean may
result in the entire lab section losing points. When you finish a lab you should clean your own
lab area and help maintain cleanliness in the general lab areas. You should always follow safe
laboratory procedures. Misconduct in the lab will result in a loss of points. If you cause harm to
others through misconduct or neglect you may receive a failing grade for the experiment.
GRADING
Grades will be based on Lab Work (which include prelab preparation, technique/safety, and lab
notebooks) as well as Lab Reports, Quizzes, and the Final Exam. The points will be as follows:
Syllabus Quiz
Lab Experiments
Lab Reports
Quizzes
Final Exam

5 points
15 points per day
15 points for a one day lab, 30 or 60 points for multistep syntheses
15 points each (lowest score will be dropped)
200 points

There will be no extra credit and TAs do not have the ability to assign extra work. Grades can be
accessed from GauchoSpace. Any concerns about grading must be brought to the instructors
attention within one week after the assignment is returned. Lab reports will be returned two lab
periods after they are turned in. Quizzes will be returned within one week after they are given. If
your TA does not regularly return your lab reports please contact Dr. Gainer.
LATE WORK
Lab work will be done in pairs unless otherwise noted. Labs reports are due one week
from the beginning of the lab period in which the lab work is completed. For each day a lab
report is turned in late you will be deducted 10% of the total possible points for the lab. Reports
that are turned in 5 days late or after dead week will not be accepted. Failure to turn in lab
reports for 3 labs will result in a failing grade.
MAKE-UP LABS
There are NO make-up labs. A pass for a missed lab will be given if the absence is
cleared through Dr. Gainer prior to the lab period. Include both Dr. Gainer and your TA in the
email when asking for an excused absence. No more than one pass will be granted per student
per quarter. Three absences will result in a failing grade. If you miss a one day lab with an
excused absence, your grade for the prelab, in lab work, and lab report will be replaced by your
average grade. If you miss a lab that is part of a multistep synthesis, you must still complete all
of the prelab information and show it to your TA at the beginning of your next lab period. You
must still include the missed labs information on the lab report (acquire any necessary

information from your lab partner). If you miss any two labs, your grade in the class will drop by
one letter score.
LAB NOTEBOOK
Accurate record keeping is essential to many fields including chemistry. Doctors are
required to take accurate, meticulous notes when speaking with patients to guarantee proper
medical care; an accountant must keep a carefully detailed record of each transaction to avoid
hassle with the IRS; a lawyers notes must be thorough and complete to avoid misinformation
being presented at a trial. Likewise, the lab notebook is a permanent record of a chemists
laboratory activities. Chemists often refer to their notebooks when applying for patents and
writing scientific papers, and when formulating conclusions before moving forward with a
research project. Additionally, the lab notebook is used as evidence when a company is taken to
court. Because of these significant implications it is important to learn data collection techniques
that prepare you for your future, regardless of your specific field of study.
Purchase a spiral bound, perforated carbonless notebook at the bookstore. This notebook
can be used for both 6AL and 6BL. Your lab book should be used to keep an organized, accurate
record of what you do and observe in lab and such be well organized and legible. Point can be
deducted for sloppy notebooks.
LAB EXPEREIMENTS
In preparation for this class you should buy a perforated, carbonless, spiral bound
notebook from the bookstore. You can use your notebook from 6AL. This notebook is to be an
accurate record of the work youve performed in the lab.
Each lab experiment will include work that is worth a total of 15 points. The points are broken
down as follows:
1. Prelab (5 points): The prelab portion of the lab must be completed prior to the beginning
of the lab session and will be checked and graded by the TA as you enter the lab. The
prelab should include the following:
A. Title, date, name, student perm number and TA overseeing the experiment
B. Purpose/Objective
Give a brief introduction to the purpose of the experiment and the
approach to be used. Demonstrate that you understand the objective and the key
concepts of the experiment. Do not copy directly from the laboratory manual.
Usually, one paragraph will be adequate (less than 1/2 a page). Use only the third
person, present tense, passive voice when writing the introduction. For example,
using third person: do not say I, we, or our. Speak as if it is happening right now
(present tense), but use a passive voice for your verbs.
Incorrect Example: I am preparing cyclohexanol from cyclohexanone by
hydride reduction.
Correct Example: Cyclohexanol is prepared from cyclohexanone by
hydride reduction.

Notice the correct example says is prepared which uses the present tense
and passive voice. It is implied that you are the one performing the experiment so
it is redundant to speak in 1st person, which is why you dont see any
grammatical person in the correct example.
C. Reaction Diagram and Mechanism
This is the balanced, fully labeled chemical equation. Each structure
should have its chemical name underneath. Usually, conditions like temperature
and the solvent used are indicated above or below the reaction arrow. Also include
an accurate arrow pushing mechanism for the reaction.
D. Table of Reagents and Products
A table of reagents needs to be completed before lab starts. Construct a
table similar to the one provided in each experiment. Any theoretical value needed
to calculate your answers or to compare your results needs to be present. Of
course, this is going to require you to read the lab and figure out what exactly you
need.
E. Procedure
This is where you lay out what you plan to do in lab. It should be
sufficiently detailed so that you can follow it during lab without referring back to
the lab manual. Do not copy directly from the laboratory manual and leave room
to make observations during the lab. Remember that the procedure section should
be sufficiently detailed, such that another student would be able to repeat the
whole experiment based on your report. Keep the following points in mind:
Use the third person, passive voice. (EXAMPLE: The reaction mixture was
heated at reflux for 30 minutes; NOT I heated the reaction mixture at reflux
for 30 minutes.)
B. Avoid the recipe format. Recipes are written in a command tense, telling
you to do something. This is not the way you should be writing your
observations.
Incorrect: Heat the solution on a hot-plate for 30 minutes.
2. Technique/Safety (5 points): During each experiment technique/safety scores will be
assigned worth 0-5 points. The technique/safety score can be very subjective. Your TA
can give you a low score if you have a messy area, use incorrect disposal techniques, are
extremely inefficient in lab, have an unorganized, unkempt notebook, are not wearing
your safety goggles, or are unprepared for lab. Failure to listen, learn, and comply will be
reflected in your technique grade and in severe cases may result in the loss of additional
points. Additionally, stockroom personnel will alert your TA if they observe unsafe
practices. Your TA can give you an outstanding score if you clean up a dirty area such as
the balance table, ask good questions, have a very neat, organized notebook, or are
efficient during lab.
3. In-Lab Actual Proceedings and Observations (5 pts): This is an account of what really
was done. You have written out the procedure in the prelab. If the procedure has been
modified or changed in any way from the original experiment, note the changes here.

Remember that the procedure section should be sufficiently detailed, such that another
student would be able to repeat the whole experiment based on your report.
Incorporate your observations into the procedure. Observations should be concisely
written. Avoid unnecessary detail. (ex) The reaction mixture turned green and a
precipitate formed. The precipitate was collected using a Buchner funnel and washed
with water. The crude product, in the form of yellow crystals, had a mass of 15.0 mg.
Included in this score are points for the quality and purity of your product (i.e. percent
yield, quality of your melting point and IR, etc).
Witness: Give your signature and a pledge that all of the observations and conclusions
herein are your own and that you believe them to be correct. Then have your TA witness
your pledge with their signature.
LAB REPORTS
All lab reports should be typed in single spaced-12pt. font with 1 margins. Points will be
deducted for poor spelling or grammar. The reports should include an introduction, a discussion
of the methods and experiments, and thorough results and conclusions sections. All figures,
graphs, charts, mechanisms, etc. should be at the end of the lab report. All references should be
cited in ACS format (see http://library.williams.edu/citing/styles/acs.php). All lab reports will be
checked against other lab reports as well as a database of other reports to detect plagiarism. Any
plagiarism detected will result in a zero for the report and potentially a failing grade for the class.
The lab reports are turned in a week after the experiment is performed. A hardcopy is
placed your TAs mailbox outside the organic chemistry lab stockroom and an electronic version
is uploaded to GauchoSpace as a .txt file. The lab report is not turned in until both the
hardcopy and the electronic copy are properly submitted. The electronic version should be
identical to the hardcopy version, the only exceptions being you do not need to draw out the
mechanism or include annotated spectra on the electronic version. The mechanism can be hand
drawn on the hardcopy, if it is done using clear, legible, arrow pushing. For more guidance on
writing the lab report, see the Tips for Writing a Good Discussion on Gauchospace.
SHORT LAB REPORTS (15 points/each)
The ability to effectively communicate the results of an experiment are just as important
as being able to accurately perform an experiment. For each lab you will write up a short lab
report. This must be a typed report that is single spaced, with 1 margins and 12 pt font. The
maximum length is one and a half pages (not including spectra or references) unless specifically
approved by your TA. The lab reports are turned in a week after the experiment is performed.
LONG LAB REPORTS
The lab report for the multi-step syntheses will be longer lab reports. The write up for
Lab 15b will be 2-3 pages in length and be worth 30 points. The write up for Labs 17b-20b will
be one lab report 4-6 pages in length and be worth 60 points. The longer lab reports should
contain similar content, and also include discussions on the overall goals of the multi-step
synthesis and on the overall yields.

QUIZZES
There will be a quiz each week at the beginning of one of the two lab periods. You should
be comfortable with the mechanism of each experiment before the lab period, as the quiz will
cover questions about the mechanism. Additionally, the quiz topics may include: general
questions about the current weeks experiments, in depth questions about the previous
experiments (including mechanism), questions on spectroscopy and safety, questions about other
topics covered in pre-lab lecture, questions from the assigned reading, as well as questions on the
techniques covered in both 6AL. There will be a total of 8 quizzes beginning the second week of
class. Your lowest quiz score will be dropped. If you miss a quiz due to an absence, this will
count as your lowest score.
FINAL EXAM
The final will be held on Saturday, March 14, 4:00-6:30pm. Plan accordingly. There will
be no makeup final and failure to take the final will result in a failing grade for the course. Please
bring a large Parscore sheet, a pencil, and a nonprogrammable/nongraphing calculator to the
exam.
PLAIGARISM
Most lab work will be done in partners. However, you must write up your prelab and lab
report completely independent of your partner. This means that before you leave lab, make sure
you have your partners data and understand fully what each of you did. Lab reports will
regularly be checked for plagiarism against current and past lab reports, as well as various online
sources of prewritten lab reports. Any questionable results will be reported to the Student
Conduct Committee, will result in a zero grade for the lab report, and may result in a failing
grade for the course
The following is from Campus Regulations:
It is expected that students attending the University of California understand and
subscribe to the ideal of academic integrity, and are willing to bear individual responsibility for
their work. Any work (written or otherwise) submitted to fulfill an academic requirement must
represent a students original work. Any act of academic dishonesty, such as cheating or
plagiarism, will subject a person to University disciplinary action. Cheating includes, but is not
limited to, looking at another students examination, referring to unauthorized notes during an
exam, providing answers, having another person take an exam for you, etc. (emphasis added)
Representing the words, ideas, or concepts of another person without appropriate attribution is
plagiarism. Whenever another persons written work is utilized, whether it be a single phrase or
longer, quotation marks must be used and sources cited. Paraphrasing anothers work, i.e.,
borrowing the ideas or concepts and putting them into ones own words, must also be
acknowledged. Although a persons state of mind and intention will be considered in determining
the University response to an act of academic dishonesty, this in no way lessens the
responsibility of the student.