Syllabus

Chemistry 6BL Winter 2014 UCSB

Instructor: Dr. Morgan Gainer

e-mail: 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 5 points

Lab Experiments 15 points per day

Lab Reports 15 points for a one day lab, 30 or 60 points for multistep syntheses

Quizzes 15 points each (lowest score will be dropped)

Final Exam 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 instructor’s

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 lab’s 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 lawyer’s notes must be thorough and complete to avoid misinformation

being presented at a trial. Likewise, the lab notebook is a permanent record of a chemist’s

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 you’ve 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 don’t 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 TA’s 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 week’s 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 partner’s 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 student’s 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 student’s 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 person’s written work is utilized, whether it be a single phrase or

longer, quotation marks must be used and sources cited. Paraphrasing another’s work, i.e.,

borrowing the ideas or concepts and putting them into one’s “own” words, must also be

acknowledged. Although a person’s 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.”