Conc. Nitric Acid 1 L

CHE 303

Summer 2003

The following page contains a list of chemicals used in this course. If you are pregnant, or have other medical problems, you may wish to visit your physician with this list and get his written permission to take this course.

Che 303 Reagents

ReagentAmount*

Bromobenzene 1500 mL

Conc. Nitric Acid 1 L

Conc Sulfuric Acid 1 L

Ethylbenzene 2 x 100 mL

KMnO4 2 x 1#

3M NaOH 2 x 2 oz

NaHSO3 2 x 1#

Celite ( filter aid ) 2 x 1#

Conc HCl 2 x 500 mL

petroleum ether 4 x 1gal.

chloroform 4 L

Methanol 2 x 1 gal

NaBH4 2 x 25 gm.

Benzophenone 2 x 500 gm.

Diethyl Ether 20 L

Anhydrous MgSO4 4 x 1 lb.

Chromic acid Reagent 2 x 1 L

Lucas Reagent (Conc.HCl and 136g ZnCl2) 2 x 1 L

2-Butanol 200 mL

1-Phenylethanol 200 mL

t-Butanol 200 mL

1-Butanol 200 mL

Cyclohexanol 2 x 1 L

Glacial Acetic Acid 4 x 500 mL

Pool Chlorine 4 x 1 L

KI Starch Paper 10 vials

Na2CO3 4 x 1 lb.

NaCl 4 x 1 lb.

2,4-Dinitrophenylhydrazine Reagent (2,4-DNPH) 1L

Tollens Reagent 500 mL

Iodoform Reagent 1 L

Dioxane 500 mL

Acetone 500 mL

Cyclohexanone 1 L

Acetophenone 100 mL

Benzaldehyde 100 mL

Methyl Benzoate 500 mL

Magnesium 1 lb.

Dry Ice 15#

Na2SO4 2 x 1 lb.

6M H2SO4 2 x 2.5 L

3M H2SO4 1 x 2.5 L

0.1000M NaOH 1 gal.

Phenolphthalein 4 bottles

*Amount necessary for 50 Students

Preface

The following handouts were expressly written for the Organic Chemistry course CHE 303, given during the summer of 2003 at California State University Dominguez Hills. They were designed to be used in conjunction with Organic Laboratory Techniques, Pavia, Kriz, Lapmann & Engel, First Edition.. This latter book will be referred to as the "laboratory text”, and is available in the bookstore.

CHEMISTRY 303 SYLLABUS

Summer 2003

Instructor: Dr. Reilly

Office Hours: NSM B-302 by appointment

Office Phone: Office (310) 243-3773

Required Text and Materials:

1)Organic Laboratory Techniques, Pavia, Kriz, Lapmann & Engel, First Edition

2)Laboratory Manual

3)Laboratory Safety Glasses

4)Latex Gloves

5)Lab Notebook, it contains carbon paper

Pre-Laboratory Discussions:

NSM C-221 -- 1:00pm, precedes laboratory sessions. Be prepared for the experiment,

so that the discussions make sense to you. You will be asked to explain

the steps involved, as well as supply results of calculations asked for

in the day's experiment. Failure to prepare will cost you lab points.

Exams, Reports, and Grading

Three 25 point quizzes will be given, along with one final exam, covering all of the experiments, which will be worth 75 points and will be given during the last lab period.

Absolutely no make-up exam will be given. Furthermore, no extra time will be allowed for those who arrive late for quizzes and exams. You are allowed and encouraged to use calculators, however, you will not be allowed to share these with other students. CALCULATE BY HAND IF CALCULATOR IS NOT WORKING. Missing the final exam means getting a zero regardless of reason. In order to receive a grade you must also check out of the laboratory according to the instructions by the stockroom.

Grading:PercentagesLetter Grade

90 - 100A

80 - 89.9B

70 - 79.9C

60 - 69.9D

Below 60F

Grades based on lab score - 300 points possible, distributed as follows:

Quizzes 75 points

Comprehensive final 75 points

Laboratory Reports 100 points

Practicum 50 points

Deductions for poor laboratory performance, and non-attendance

Deductions from total lab score for:

1.Disrupting the class.

2.Cheating means an "F" for the course even if cheating is done on only one test. Some examples of cheating are:

a.Looking at someone elses paper or allowing someone else to look at your paper.

b.EXCHANGING calculators. If you do not bring one into class, or if the one you bring fails

to function properly, do the calculations by hand.

c.Looking at open books, pieces of paper, looking ANYWHERE you can read what is facing you.

d.Writing, printing, etc. on desks, walls, persons, etc. that you can read.

e.Communicating with any other student in any way during test or quiz.

f.You causing the professor in charge to question your behavior during the test.

g.Turning in a lab report when you did not do the experiment.

NOTE: This list is not an exhaustive one, but is given to let you know

that Dr. Lyle and I consider cheating a serious breach of academic

etiquette. If you wish to dishonor your name, that is your business, but to

dishonor the class' is ours and we won't permit it.

1. Not wearing glasses (-5 points each time) or wearing shoes which do not protect

the tops of your feet and toes (-5 points each time).

1. Being a hazard to others (removal from laboratory, plus loss of up to 100 points –

the penalty dependent on the severity of the infraction.)

5.Mishandling laboratory equipment (2 - 5 points)

1. Not being prepared for lab, including not attending lab -10 points deducted for

each absence.

7.Failure to perform assigned experiments constitutes non-completion of course

requirements, and will result in a failing grade.

8.Failure to observe safety regulations.

9.Not doing homework.

Supplementary Rules for Laboratory Classes Taught by Dr. Reilly

1.No weapons are allowed in the laboratory. There is no need for them on this campus. There will be a deduction of 40 points and a visit to the Dean at the occurrence of the first offense.

2.All persons in the laboratory must be sober and not under the influence of drugs. Some of the electrical instruments use 35 amps and 220 volts. Carelessness with these instruments and others, demanding equal respect, may endanger others in the lab. Any person whose behavior presents unsafe conditions in the opinion of the instructor will be dismissed from the laboratory, suffer a loss of 40 points, and must endure a visit to the Dean.

3.No visitors are allowed in the laboratory. Social hour is to be held elsewhere. There will be a deduction of 10 points for each occurrence.

4.No selling of jewelry, vitamins, candy bars, etc. is permitted in the laboratory. The laboratory is not a Convenience Store. There will be a deduction of 40 points for each occurrence.

5.No placing of posters or making announcements about campus events is allowed in the laboratory. You are in the laboratory for one reason only and guess what that is. There will be a deduction of 10 points for each occurrence.

6.No removal of supplies or equipment is permitted. Depending on what is taken, there will be a deduction of 10-100 points, a visit to the Dean and the Public Safety Officer with the first occurrence.

7.A list of chemicals used and stored in the laboratory will be available to you from our friendly technical support staff. In the meantime if you have any questions about the chemicals used in the course, I will try to get you the necessary information. If you are pregnant, or have other medical problems, you may wish to visit your physician with the list and get his or her written permission to take this course. Show me the written permission.

8.Giving birth to a child or children in the laboratory is not allowed. Such an event distracts everyone from concentrating on the important experiment assigned. Such an event also means that you ignored your physician's instructions. There will be a deduction of 20 points per child.

9.Boisterous, amorous, or other disruptive behavior in the laboratory is not allowed. Such behavior can endanger others in the laboratory. There will be a deduction of 100 points and a visit to the Dean after the first occurrence.

10.Unauthorized experiments in the laboratory are not allowed. You have enough to do with the authorized experiments, if you do not, you have not performed them correctly. There will be deductions of 10-100 points and a possible visit to the Dean, depending on the severity of the infraction.

11.Eating or drinking in the laboratory is prohibited, as the microbes in the air do not possess any nutritional value to humans. A dedcuction of 5 points for each occurrence will be made.

12.Additional Safety Requirements:

1)Glasses, to protect eyes.

2)Shoes, NOT SANDALS, to protect feet.

3)Aprons or lab coats to protect dignity.

4)Latex gloves will be worn while working in the lab.

A deduction of 5 points will be made for each occurrence.

13.No mouth pipetting or tasting of chemicals is permitted. None of these chemicals will make a good lunch.

14.Failure to follow the written instructions in the handout or lab book, the written and oral instructions of the instructor, and failure to report accidents is prohibited. There will be a deduction of 5-100 points and a possible visit to the Dean, depending upon the severity of the infraction.

15.Damaging or mistreatment of instruments and equipment is prohibited. Chemistry experimentation is not a preparation for the Demolition Derby. There will be a deduction of 5-100 points, and a possible visit to the Dean, depending upon the extent of the damage.

Laboratory Reports

They are the top pages (white) of your Lab Notebook. Use the following format.

NameTitle of ExperimentDate

Laboratory Data:(1) Draw balanced equation.

(2) Complete table which is at the beginning of each experiment. Use the amounts of reactants that you actually use. Calculate the maximum possible amount for each product.

(3) Any observations that you see during the experiment.

(4) Distillation tables.

Laboratory Results:(a) Record the weight (and the volume if product is a liquid). Include the "tare" weight even if it is zero.

(b) % yield of the product you want. Use the equation, the molecular weights, and the densities given to you at the beginning of each experiment.

(c) Graphs, if applicable.

(d) Any other items required by the instructions of a specific experiment.

(e) Any conclusions that might be needed.

Laboratory reports are due at the beginning of the period (DURING THE PRE-LABORATORY SESSION) following the one in which the experiment was completed. A lab report is considered late if turned in AFTER the pre-laboratory session. For every period that a report is late, there will be a deduction of 5 points, until zero is reached.

Homework

Homework consists of the exercises at the end of each experiment. they are to be handed in when the laboratory reports are, but on separate sheets of paper.

Tests

Your final exam will be administered in C-221 - the lecture/pre-lab room. Before you go to C-221, take your books, purses, "suitcases", etc., to your regular lab and LEAVE them there. Bring only your calculators, pencils and brains to the test. Once you have entered the test site, you can NOT leave, so make sure you have taken care of your "needs" beforehand.

Chemistry 303

SUMMER 2002

Points for Lab Reports, Quizzes and Exams

ExperimentPoints

EAS Nitration of Bromobenzene 10

Thin Layer Chromatography 10

Arene Oxidation 10

Determination of Benzoic Acid Molecular Weight 5

IR/NMR Experiment 10

Reduction of Benzophenone 10

Alcohol Classification Tests 5

Oxidation of Cyclohexanol to Cyclohexanone 10

Carbonyl Classification Tests 5

Triphenylmethanol Via Grignard 25

Oxidation Practicum 50

Quizzes 75

Comprehensive final 75

Course Total 300

Study Guides for Che 303
YOU ARE RESPONSIBLE FOR ALL MATERIAL CONTAINED IN YOUR LABORATORY EXPERIMENTS, DISCUSSED IN PRE LAB, OR DISCUSSED IN LAB.
The exercises at the end of each experiment will help you answer most of the test questions. You Must know the structures and names of every chemical used, except those specifically excluded by the instructor.

Schedule of Laboratory Exercises

TUESDAY / WEDNESDAY / THURSDAY
July 08th
Orientation
Check-In / July 09th
EAS Nitration of Bromobenzene Disc.
EAS Nitration / July10th
TLC/Arene Ox. Discussion
EAS Nitration/TLC
EAS Melting Range(s)
July 15th
QUIZ: 15 mins., 25 pts.
EAS, TLC
Arene Oxidation Reflux / July 16th
IR/NMR Discussion
Arene Ox., Cont'd / July 17th
Carbonyl Reduction discussion
Molecular Weight Determination
Melting Range of Oxidation Product
IR/NMR Experiment
July 22nd
QUIZ: 15 mins., 25 pts.
Arene Oxidation, IR/NMR
Alcohol Tests Disc.
Carbonyl Reduction / July 23rd
Cyclohexanol Oxidation
Discussion
Melting range of Carbonyl Reduction
Alcohol Tests / July 24th
Carbonyl Tests discussion
Cyclohexanol Oxidation Experiment
Jul 29th
QUIZ: 15 mins., 25 pts.
R-OH Tests, C=O Ox., C=O Red'n
Grignard Discussion
C=O Classification Tests / Jul 30th
Grignard Reagent Synthesis/react with Methyl Benzoate / Jul 31st
Practicum Discussion
Grignard, Cont'd
Aug 05th
Melting Point Determination for Grignard products
Adipic Acid Practicum / Aug 06th
Practicum, Cont'd
Melting range of Practicum product
TURN IN REPORT BY THE END OF THE PERIOD / Aug 07th
Final Exam
75 Pts., 1 Hr.
Check-Out