Organic Chemistry Laboratory: CH 2011

Syllabus, Fall 2013

Room 339 Hunter Lab (Sections 012 & 013 on Monday night are in Hunter 329)

Laboratory Manual: Organic Chemistry Lab – CHL 201 (left over from last year’s
course title), T.K. Vinod and L. E. Craine 13th ed. Houghton-Mifflin,
Boston, 2012. ISBN-10: 1-111-42584-1

Required: Laboratory Notebook: Clemson University Department of Chemistry

Carbonless Lab Note Book (You can use the one you used previously in
General Chemistry.)

SAFETY NOTES: Read the Safety Rules in your Laboratory Manual prior to meeting your
first lab (pp ix-xi).
SEE PAGE 5 OF THIS SYLLABUS.

The schedule outlined for the course is tentative and may be subject to change .

CHEMISTRY 2011 LABORATORY SCHEDULE

Date Experiment Page #

Check In, Form Groups, Overview of Lab Procedures, Safety Quiz
Sept 2 – 6 “Melting-Point Determination: Purity and Identity of Crystalline Organic 1
Compounds” Sections 1, 2, 3, 4, 5, 6
Recrystallization: Purification of Crystalline Organic Compounds 1, 2, 4,
Sept 9– 13 11
5 (macroscale only of Sections 4 & 5)
Sep 16 – 20 Distillation: Separation and Purification of Organic Liquids 1, 2, 3, 5 23
Extraction: A Separation and Isolation Technique Sections 1, 2, 3, 4
Sep 23 – 27 33
(macroscale only of Section 4)
Chromatography I: Gas, Thin-Layer and Paper: Parts B1, B3 (separation
Sept 30 – Oct 4 59
of paprika pigments), C1, C2, D1, D2, D3
Oct 7 – 11 Dyes and Dyeing: Sections 1, 2, 3, 4 351
Fall Break (no labs)
Oct 14 – 18 Except Sections 005, 006, 007 (Thursday) You Will do Electrophilic 149
Aromatic Substitution Section A 1, A 2 (macroscale only)
“Synthesis of an alkene (Cyclohexene) from an alcohol (Cyclohexanol)”;
Oct 21 ­ 25 Tests for Unsaturation Sections A (macroscale only), C 107
Peer Evaluations I
Synthesis of Alkyl Halides Sections A 1, 2 (macroscale only); Sections B
Oct 28 – Nov 1 199
&C
Synthesis of Alkyl Halides Section A 3 (macroscale only); Sections B &
Nov 4 – 8 199
C
Electrophilic Aromatic Substitution Section A 1, A 2 (macroscale only)
Nov 11 – 15 149
Except Sections 005, 006, 007 (Thursday) Which WILL NOT MEET
Nov 18 - 22 Thanksgiving Break (no labs)
Nov 25 – 29 Diels-Alder Reaction 133
Check Out
Dec 2 ­ 6
Peer Evaluations II, TA Evaluations, Course Evaluations

The schedule outlined for the course is tentative and may be subject to change.
Important Dates
The last day to register or add a class is Tuesday August 27th.
The first day of lab is Monday September 2nd. (We will labor on Labor Day!)
The last day to drop a class or withdraw from the University without a W
grade is Tuesday September 3rd.
The last day to drop a class or withdraw from the University without a final
grade is Tuesday October 29th.
Fall Break is Monday and Tuesday October 14th and 15th. There will be NO
LABS this entire week Except for Thursday! All Thursday labs will meet on
October 17th. This is to make up for not having lab on November 14th because
of the football game that night.
Thanksgiving holidays are Wednesday – Friday November 27th – 29th. There will
be NO LABS this entire week.
The last day of labs is Friday December 6th.

1. The grade in the course is based on a total of 100 points which are
distributed as follows:

Points
(a) Laboratory Notebook 30
(b) Questions 20
(c) Pre-lab exercises 20
(d) Technique 25
(e) Peer Evaluations 5

a. Your TA will collect your notebook sheets at the conclusion of each

experiment (See notebook format, next page).
b. Pre-lab exercises for each week’s experiment will be given, and will be
due at the beginning of that laboratory period. If the pre-lab is not
completed satisfactorily you will not be allowed to perform the
experiment and will receive a grade of zero for the experiment.
c. Questions from the Lab Manual will be turned in the week following
completion of that experiment.
d. Your TA will make a subjective judgment which will include: your
preparation for the experiments; your ability to work independently; your
participation; your observance of lab safety; your practice of lab
housekeeping; etc.
e. Peer Evaluations will be conducted in the middle and at the end of the
semester and will total 5 points.

2. The grading scale will be:

90 and above A
80 - 89 B
70 - 79 C
60 - 69 D
below 60 F

3. You will work in groups.

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4. Attendance in this lab is required. You will not receive credit for missed work
and your team members may decide to penalize you on peer evaluations. If you
have to miss a lab for some valid reason you should inform the members of
your group and your TA. If you have more than one unauthorized absence the
laboratory instructor may drop you from the course. In addition, you will lose 5
pts from your possible point total (or one-half a letter grade) for the
unauthorized absence. We do not make up missed labs, but you must still
submit a pre-lab and post-lab (get data from group members if necessary) for
grading. You will not be graded on notebook pages or technique for a missed
lab.

5. Students who do not follow the safety rules will be dropped from the
course.

6. Late work will be penalized 10% per day late.

Notebook
You are required to submit carbon copies of your lab notebook pages. This is one of students’ least
favorite (most hated?) activities in lab. Nevertheless, you are taking a chemistry course and you are
expected to act like chemists.
 A bound notebook is required. You may use the one you used in general chemistry.
 The write­up must be written in ink. 
 Right hand pages are used for the write up.
 Left hand pages are for calculations, notes.  These will not be graded.

Notebook Format (for the first six experiments and general observations)

a. The notebook is a day­to­day record of your activities in the lab.  It is the place where
you will describe experiments as you do them and note observations as you make them.
It is where you will record and analyze your data.  Your notebook will be an invaluable
tool throughout the semester, as you must have an accurate record of what you did and
what you observed in the laboratory when the time comes to write your laboratory report.
b. All data, results and weights, etc. should be  recorded directly into your notebook in
ink.  Loose pieces of paper might easily get lost.  Remember that it is to your benefit to
keep a detailed notebook, which will make it easier for you to reconstruct the experiment
accurately in a report later.  Any mistakes should be crossed out so that they can still be
read.  They should not be erased or removed with "white­out".
c. The   notebook   should  not  be   a   neatly  copied   reiteration   of   the   laboratory   procedure.
Rather, you should write what you did and observed.  Neatness, spelling, punctuation and
grammar are not essential in this notebook, but it should be possible for someone else to
repeat   your   work   by   reading   your   account,   i.e.,   it   should   be   legible   and   intelligible.
“Real” chemists working in industrial labs are required to do this, so just use this thought
as a measure of your notebook success, “could one of my group members miss a lab but
make it up by only using the procedure found in my notebook?” If you can honestly
answer “Yes” then your notebook write­up is fine.

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d. Your lab instructor will read your notebook in order to see whether you are keeping up
with   your   work,   whether   you   understand   what   you   are   doing,   and   whether   you   are
recording everything you need. 
e. Since   the   lab   notebook   should   be   used   for   recording   everything   that   you   do   in   the
laboratory there is not one particular format that can be used for all situations, and it is
important to be flexible. However there are certain things you should do to make the lab
notebook as useful as possible.
f. Leave   a   few   pages   blank   at   the   beginning   of   the   notebook.   As   you   begin   new
experiments and projects you can use these pages to prepare a table of contents that can
be updated as you go.

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 Notebook Format (for experiments done after Fall Break; they are
synthesis labs)
1. Title of experiment
2. Purpose of experiment
3. Main reaction
4. Table of reagents

: Reagent : Molecular Weight : wt (g) : Volume (ml) : no. of

moles

: : : : :

5. Limiting reagent
6. Theoretical yield (show calculations)
7. Procedure: This should include what is actually done and is observed.
This section should not be prepared in advance. It must be written in
the passive voice, past tense.
8. Percentage yield
9. Melting Point (if product is a solid) or Boiling Point (if product is a liquid)
10. Conclusion and any additional comments
11. References (if other than the laboratory text)

SECTIONS 1-6 and 11-12 MUST BE PREPARED BEFORE COMING TO CLASS.

CH 201L Objectives

After this course you will be able to:

1. Demonstrate common organic laboratory techniques.
2. Indicate when and how and why these laboratory techniques are performed.
3. Record data and observations accurately.
4. Synthesize, isolate and purify organic compounds.
5. Develop experimental procedures.
6. Communicate the results and conclusions of experiments in writing.
7. Work cooperatively with other students to reach the goals of experiments.

The faculty coordinator for CH. 201L is Dr. Sean O’Connor, office: 267 Hunter
Laboratory, e-mail: oconns@clemson.edu Tel: 656-1537. Although most problems
should be able to be handled by the laboratory instructors, the faculty
coordinator should be consulted if any problems arise.

The above schedule, policies, procedures, and assignments in this course are
subject to change in the event of extenuating circumstances, by mutual
agreement, and/or to ensure better student learning.

Accommodations:
Students with disabilities needing accommodations should contact the Office of
Student Disability Services, 864-656-6848 and Clemson University Student
Disability Services. Prior to receiving accommodations a student must obtain a

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Faculty Accommodation Letter from that office. Please bring the letter to your TA or
the laboratory coordinator.

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 Organic Laboratory Safety Rules

1. Material Safety Data Sheets (MSDSs) for all chemicals used in the organic laboratory are available in
the organic stockroom. Please ask for them if you wish to know about the chemicals you are using in lab.

2. Wear eye protection at all times. Locate the eyewash stations and know how to use them. Even if you
wear prescription glasses, wear safety goggles over them. Wear approved eye protection at all times while in
the laboratory and in any area where chemicals are stored or handled. There is a technique grade reduction for
every violation of this policy.

3. Eye protection should protect against impact and chemical splashes. Goggles may be rented from the
organic stockroom ($3.00/rental). You will have a ten-point technique grade reduction for that week.
Subsequent rentals in following weeks will result in an additional ten-point grade reduction (e.g. twenty points
the second week, thirty points the third week, etc.) The cost will still be $3.00 per rental. Your technique
grade may be a negative number.

Wearing contact lenses in the chemistry laboratory is dangerous and you should not wear them. However, if
you insist on wearing them, you must sign the Contact Lens Waiver Form.

The laboratory has an eyewash fountain for your use. In the event that a chemical splashes near your eyes, use
the fountain before the material runs behind your safety glasses and into your eyes. You should irrigate your
eyes for at least five minutes and call your instructor.

4. Eating, drinking and smoking are prohibited in the laboratory at all times. There are trashcans
outside the doors of the organic labs. If you must eat during lab time, please consume your snack and/or drink
outside the lab and dispose of your food wrappers and drink cans or bottles in the trashcan outside the lab
door. We are not allowed to even have empty food wrappers, drink bottles or cans in the lab trashcans. If you
have food in the lab or a drink container in lab with liquid in it you will have to move the food and/or drink
and/or cigarettes to the hallway. You are not even allowed to keep it in your backpack in the lab. There is a
technique grade reduction for every violation of this policy.

5. You are required to wear a lab coat in the laboratory at all times. Lab coats may be rented from the
organic stockroom ($2.00/rental). You will have a ten-point technique grade reduction for that week.
Subsequent rentals in following weeks will result in an additional ten-point grade reduction (e.g. twenty points
the second week, thirty points the third week, etc.). Your technique grade may be a negative
number.

6. Wear appropriate clothing in the laboratory in order to provide maximum body coverage. Shorts,
skirts, etc. are completely inappropriate. Your clothing should come to at least your ankles. No skin should be
visible below the waist. To be safe, wear long pants and socks. Tights or leggings are not allowed.

7. Wearing open-toed shoes and sandals is not allowed in lab. Your footwear must be non-woven and
cover your foot back to your instep. Leather or rubber shoes are good for this purpose. “Ballet flats” are
not allowed in lab.

8. If you come to lab dressed inappropriately you must leave, obtain the correct clothing and then return.
This will be a technique grade reduction. As with lab coats and goggles, subsequent transgressions result in
additional point reductions.

9. It is advisable to wear old clothes in the laboratory in case of spills; you might also want to keep a
pair of sweat pants in your drawer.

10. Backpacks, purses, coats, jackets, computers and anything else you bring to lab and are not using
must be properly stored. Do not leave them on the floor, on the stools, or on the benches. You must use either
the cubbyholes at the end of the lab or empty cabinets underneath your lab bench. There is a ten-point
technique grade reduction for every violation of this policy.

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 APPENDIX

Additional Safety Documents

See following link. This link is also found on the CH 2280 website.

Organic Chemistry Teaching Laboratory Forms for Safety Teams