Organic Chemistry Laboratory I, Chem 217

FALL 2009

Dr. Suzanne Theresa Mabrouk

General Information

Class Schedule: M 2-4:50 pm (T 1-3:50 pm) in Byrd Hall room 302 and 410.
Office Number: Byrd Hall room 401.
Office Hours: If you have difficulty with course concepts or have questions, please feel free to drop by for help. Keep in mind that regular help will assist you in mastering the material. If you find that I am already helping other students during office hours, ask if you may join. I usually help more than one student at a time, with each student interject questions.
- M 10-11 am
- W 1-2 pm
- R 9-10 am
- F 9-10 am
- open door policy
- appointments
Phone Number: 953-7788
Email Address: mabrouks@citadel.edu
If you need help at night, the best way to reach me is via email. I am never receptive to phone calls at home.

General Course Information

Required Text:
- Computation Notebook
- Experimental Organic Chemistry: A Miniscale & Microscale Approach by Gilbert & Martin, 4th ed.
- A Short Guide to Writing About Chemistry by Herbert Beall and John Trimbur, 2nd ed.
Blackboard Materials (Bb):
- Lecture Notes
- Material Safety Data Sheets (MSDS) (SIRI MSDS Index: http://hazard.com/msds/).
Required Equipment: Students must purchase the following items from the cadet bookstore and bring them to the laboratory for storage in student locker: laboratory goggles and apron. Students should bring a calculator to each class.
Course Prerequisites:
- Chem 151, 152, 161, and 162
- Each student should know how to work safely in the chemistry lab.
Co-requisite: Chem 207
Course Content: Each student will learn standard organic laboratory techniques (simple, fractional, and steam distillation; extraction; recrystallization; TLC; column chromatography; and GC-MS) and gain some experience in the synthesis and characterization (bp, mp, TLC, and GC, where applicable) of organic compounds. Reactions presented in Chem 207, Organic Chemistry I will be studied. Students will learn how to find safety information on chemicals and how to keep a scientific lab notebook.
Course Objective: By the end of this lab course, students will be able:
1. to synthesize organic compounds
2. to characterize these same compounds via chemical tests and other analyses
3. to find and understand the hazards on any chemical.
Laboratory Lectures

All lectures have been posted to WebCT. These can be accessed using the student's six-digit CIT number without the letters CIT or any dashes as the username. Initially the password is set to the last four digits of a student's social security number; the password can be re-set at any time by the student.
Students should print these notes and bring them to lecture so that the notes can be annotated. Students should study these notes ahead of time.

Course Notebook: Students should keep their lecture notes, graded laboratory reports, and quizzes in a three-ring notebook. By keeping all material pertaining to a class in the same place, students can easily find information whenever necessary. Students can also keep track of their own performance in class and calculate their grade to date.
Electronic devices: PDAs and laptop computers are allowed in the classroom for note taking only. Cell phones must be set on vibrate or silent. Students must bring a calculator to each class meeting for working problems. The calculator may not be pre-programmed with formulas and no conversion keys on the calculator may be used. Only calculators may be on the desk during a quiz. Only calculators may be used on quizzes (no PDAs, cell phones, and other alterantive electronic devices, which can contain additional aids. Calculators may not be shared. The instructor will not lend calculators to students.

Course Grading Policy

Honor in the Class: All students will adhere to the Citadel honor code described in The Guidon, and as such will not cheat on any work submitted to the instructor for a grade. Cheating will not be tolerated and any violations will be submitted to the honor court! Quizzes will be taken indepenedently of any people, written material, lecture notes, or textbooks. Lab reports will be written independently of any people or old reports.
Quizzes: Quizzes will be given on each experiment (the week following its completion) and the syllabus/laboratory safety (pp. 1-39 in the laboratory textbook, including the glassware on pp. 37-39). The quiz will address (1) the last experiment (the related lab techniques, chemical hazards, and chemical concepts including reactions and mechanisms) and (2) the reading of the new experiment, the Short Guide, and safety hazards (MSDS) of chemicals. Quizzes will only be given at the beginning of the lab period. Make-ups will only be given to students who have missed lab due to an illness or family emergency. At the end of the semester, the lowest quiz will be dropped. The remaining quizzes will be averaged to give 60% of the final course grade.
Laboratory Notebook: By Friday at 10 am of the week in which an experiment is completed, each student will submit the white copy of the corresponding lab report. Lab reports will be written independently. (See Keeping a Laboratory Notebook for more details.) Lab reports will not be accepted after Friday at 10 am. At the end of the semester, the lowest lab report grade will be dropped and the remaining averaged for 40% of the final course grade.
Final Exam: There is no final exam in this lab course.
Lab Duty: Each week, each student will sign-up for a specific clean-up duty . This task must be performed following completion of the experiment and before leaving the laboratory. The student must then have that area and their bench checked by the instructor before leaving . Until the instructor approves the work, the student may not leave.
Midterm Grade: All quizzes and lab reports will count towards the midterm grade. Grades will be determined as described below.
Final Course Grade: At the end of the course, the one lowest quiz grade and the one lowest lab report grade will be dropped and the remainder averaged independently. The quiz average will constitue 60% of the course grade and lab reports 40%.
Scale for Final Course Grades:
- A: 100-90
- B: 89-80
- C: 79-70
- D: 69-60
- F: 59-0

LD Students

It is the responsibility of these students to provide the professor with written documentation from OASIS regarding any special needs. According to Citadel policy, all letters addressing special needs must be processed by OASIS. Letters from OASIS must be received by this professor at least two days prior to the quiz and mutually acceptable arrangements must be made by this same timeframe between the professor and the student. All quizzes will be administered in the presence of this professor.

Laboratory Class Format

On quiz days, students will be allowed to ask questions about the previous experiment and the reading for the new experiment at the beginning of class.
The quiz will be adminstered for 15-20 minutes.
A brief and thorough lecture will be given on the next week's experiments.
On each laboratory day, students will conduct the experiment in compliance with safety regulations.
Students will clean their bench space.
Students will return all standard issue equipment to the locked drawer and all borrowed equipment to the appropriate location in the lab room.
Students will perform a lab duty and obtain the professor's approval for all work before leaving lab.
Students will show their written procedure and all collected data to the professor before leaving lab.

Laboratory Attendance and Etiquette (labconduct.htm)

Attendance at each lab is mandatory, as described in the college catalog p. 25. Students are not excused for any reason from lab. Students who miss a lab will earn a 0 on the missed quiz and unsubmitted report; they are still held accountable for the missed experiment and as such will be required to take the next quiz on their return. There are no make-ups, regardless of circumstances (legitimate or not)!
- Students should arrive on-time if not early.
- Tardy students should enter class quietly and take their seat. They should not ask the professor to repeat previously stated material.
Students are held repsonsible for learning all material discussed in class and performed in the laboratory, even when a student is absent. Absent students should copy the notes of classmates and discuss any difficulties with the professor before the next experiment, since the student will be required to take the quiz on the missed material.
Students should not speak while the professor or a classmate is speaking.
Students should speak respectfully to the professor and all classmates.
When a student has a question, the student should raise the hand and wait to be recognized.
- Record the question in the margins of your notes along with the professor's response. This information will be invaluable as you study.
Sleeping is prohibited in this professor's classroom. The first time a student is caught sleeping the student will be directed to the back of the classroom. The second offense by any student will result in the removal of that student and any future sleeping student from the classroom. Sleeping during class prevents one from learning important concepts and the appropriate safety hazards of the experiment. Any student removed from the lecture will not be allowed to conduct the day's experiment, since critical safety information is given during the lecture.
I will take attendance in the lab room, about halfway through the experiment. Students who take the lab quiz but do not perform the experiment will be turned into the Commandant's Office as Leaving Class without permission.
Students will not be allowed to enter class late.
Food, drink, smoking, and tobacco are prohibited in Byrd Hall.
The use of profane language is unacceptable in the presence of this professor.
Uniforms should not be fixed in the lab room.

Student's Attitude

Since you may want a letter of recommendation in the future, conduct yourself in a professional way. Remember your words, attitude, and work ethic leave a lasting impression in the minds of those around you, including the professor. Therefore, ...

be present, both in body and mind (the latter being most important!)
be presentable (clean and kempt)
have a positive attitude
be friendly
be outgoing
ask genuine questions
try to learn the material
ask for help early
make good and effective use of your time and the time of others
have meaningful conversations
choose your words carefully and wisely
above all else be genuine

How to Study for Chem 217 Quizzes

Organic chemistry laboratory classes require regular study. Students expecting to study the night before a quiz and do well will find that this technique results in a test score of F. If you would like to succeed in Chem 218 study regularly by doing the following...

attend all laboratory classes, discuss excuse with professor so that work might still be made-up
read the related experiment in the course textbook/handout, jotting questions into the margins
print and read laboratory notes from WebCT before the next class meeting, jotting questions into the margins
ask questions during class
stop by the professor's office with questions; bring your notes, flashcards, and textbook with you
prepare and study flashcards of each term/concept (term on one side and definition on reverse side) and organic reaction in the experiment (main, side, chemical test, and other reactions) using index cards (place reactants on one side and products on the reverse side of the card)
re-write each mechanism from the notes (with organic reaction at top of page and mechanism below) while talking it through (follow example of professor from class); write mechanism several times with notes beside you and then start writing it without any notes present
study the organic experiments with classmates, taking turns to quiz each other on the details of the experiment
think about the purpose of each step of the experimental procedure and how you conducted each step
know the name and appearance of each piece of equipment used in each step of the procedure
know the purpose of any chemical test reactions and the evidence and conclusion for a positive test
know how to interpret any collected data from the experiment
know how to perform any necessary calculations and their siginificance

Quiz Attendance and Etiquette

Quizzes can not be made up regardless of circumstances, legitimate or not!
Quizzes are closed book.
Quizzes will not be scaled, regardless of class performance.
Do not use red pen to write your quiz, since the professor will be using red ink to grade the test/final exam. Pencil is best, since you can erase mistakes.
Students may only use scrap paper provided by the professor. All used scrap paper must be submitted to the professor at the end of the quiz.
Be quiet during a quiz.
If you have a question during the quiz, leave your seat, bring your quiz, and whisper your question to the professor. The only legitimate questions are those for which the student is seeking clarification of a quiz question.
Print and sign your complete name on each quiz in order for a grade to be awarded.
After you have submitted your quiz, do not ask the professor to assess the quality of your quiz answers. Such discussions are distracting to classmates who are still writing the quiz.
Quiz scores will only be made available at the next class meeting and not before. Quizzes will not be given to classmates in compliance with FERPA.

Quiz Taking Strategies

Prior to starting the quiz, obtain scrap paper from the professor and jot down any charts or helpful information that may become mangled in your mind later. Then you can consult this information while writing the quiz.
Solve all problems that you know immediately, skipping all others at the present time. Place a star beside any questions that you are skipping temporarily.
After solving the easy problems, solve those with a star beside them.
Throughout the testing period look at the clock so that you work with regard to the availability of time. Do not expect nor demand extra time from the professor to complete your quiz. No extra time will be granted.

Lab Schedule

Note: Miniscale procedures will be followed.

Date	Experiment	Reading
August 31	Syllabus. Class Discussion on Laboratory Reports & Laboratory Safety (MSDS).	pp. 1-39. Short Guide ch. 4.
September 7	Two-Base Extraction: B (pp. 158-159). Class Discussion on Studying Chemistry. Quiz.	pp. 149-159. Section 2.21. Short Guide ch. 3. MSDS of benzoic acid, naphthalene, diethyl ether, sodium hydroxide, & hydrochloric acid.
September 14	Recrystallization of Benzoic Acid from Two-Base Extraction: B.1 (pp. 103-104). Class Discussion on Scientific Honesty	pp. 93-104. Sections 2.9-2.11, 2.17, & 2.18. Short Guide ch. 2. MSDS of benzoic acid.
September 21	Recrystallization of Naphthalene from Two-Base Extraction: B.1 (pp. 105). Determining Capillary-Tube Melting Point of Isolated Benzoic Acid from Two-Base Extraction.	pp. 113-119. Sections 2.7, 2.9-2.11, 2.17, & 2.18. Short Guide pp. 103-112. MSDS of benzoic acid, naphthalene, 2-naphthol, diethyl ether, sodium hydroxide, sodium bicarbonate, & hydrochloric acid.
September 28	Isolation of Trimyristin from Nutmeg & Determining Capillary-Tube Melting Point of Naphthalene from Two-Base Extraction. Preparation of Ethanol. Quiz.	pp. 167-174. Handout. Section 2.7, 2.13, 2.21, 2.22, & 2.29. J. Chem. Educ. 1952, 29, 290-1, J. Chem. Educ. 1962, 39, 203-6, and J. Chem. Educ. 1962, 39, 246-251 in blackboard.citadel.edu. MSDS of acetone, diethyl ether, & trimyristin.
October 5	Simple Distillation of Ethanol. Preparation of Ethanol. Quiz.	pp. 123-128. Handout. Sections 2.2, 2.4, & 2.13. MSDS of ethanol.
October 12	Fractional Distillation of Ethanol.	pp. 131-136. Handout Section 2.14. MSDS of ethanol.
October 19	Steam Distillation: Isolation of Citral from Lemon Grass oil, Baeyer Test for Unsaturation, & Tollens' Test for Aldehydes. Quiz.	pp. 141-145, 817-830, 844, 852-853. Sections 2.16 & 2.19. MSDS of acetone, diethyl ether, & citral.
October 26	Gas Chromatography (GC) of Citral.	pp. 175-176 and 192-202.
November 2 & 9	Dehydration of Cyclohexanol (B), Baeyer Test for Unsaturation, and GC of Cyclohexanol. Quiz (Nov. 2).	pp. 344-351, 852-853, 175-176 and 192-202. MSDS of cyclohexanol, sulfuric acid, cyclohexene, cyclohexanol, & potassium permanganate.
November 16	Dehydrobromination of Meso-Stilbene Dibromide and Baeyer Test for Unsaturation. Quiz.	pp. 395-401 and 852-3. Sections 2.9, 2.10, and 2.17. MSDS of meso-stilbene dibromide, potassium hydroxide, triethylene glycol, & ethanol.
November 30	Separation of Spinach Pigments by TLC. Quiz.	pp. 175-182. Section 2.21. J. Chem. Educ. 1962, 39, 246-51 in blackboard.citadel.edu. MSDS of petroleum ether, acetone, ethanol, & sodium sulfate.
December 7	Quiz, Check-out, & Evaluations.

Lab Practices

To prevent food poisoning from chemicals in the lab, food, drink, tobacco, smoking, and gum are all prohibited in the organic lab.
To prevent eye loss, students must wear goggles at all times while working in the organic chemistry lab. Any student caught working without adequate eye protection will be required to wash their eyes at the eyewash station.
Sandals or slippers may not be worn in the lab, as they do not protect the feet from broken glass or spills.
Long hair must be pulled back and secured behind the head.
To prevent spilling chemicals onto the legs, students should wear adequate protection. Trousers are best. If shorts or skirts are worn, then an apron will help protect the thigh region.
Students must learn the hazards of the chemicals listed in the third column of the Lab Schedule above so that they handle the chemicals appropriately; this information will be tested on quizzes as well. The MSDS information can be found on WebCT.
Students will alert the lab professor of broken glassware, mercury spills, and any accidents that happen.
Students will adhere to general safety precautions and those specific ones given for each experiment to minimize risk.
Any student endangering the life of a classmate or the professor will be removed from the lab.
To minimize exposure to harmful chemicals, students will recap bottles following usage.
Students should not hold the head directly above any solvent or solution, since many vapors are harmful.
Huffing and sniffing are prohibited in the laboratory. Wafting is the appropriate technique and should only be done when indicated by the professor.
When a procedure indicates to conduct an experiment or a portion of the experiment in the hood, the student should do so for safety reasons.
Students will dump all chemicals in the appropriate waste bottle in the hood.
Students will clean their bench space after each expertiment, leaving it empty of all glassware and other paraphenalia.
No chemicals may be weighed directly on the pan of the balance. Chemicals should either be weighed in weigh trays or glassware, as appropriate.
Organic liquids should be weighed directly into glassware, as they will destroy weigh trays.
Students will return all of their issued equipment to their locked drawer before leaving the laboratory each day.
Students will return all borrowed equipment to the appropriate location in the toom before leaving each day.
No chemicals or equipment may leave the laboratory.

This page was created by Dr. Suzanne T. Mabrouk (mabrouks@citadel.edu) on 8/98 (last updated: 8/21/09).