MABROUK-Chem218

Organic Chemistry Laboratory II, Chem 218

Summer 2009

Dr. Suzanne Theresa Mabrouk

General Information

Class Schedule:
- T, W, and R 10 am - 12 pm Experiment in Rooms 410 and 412
- F 10 am - 12 pm Quiz and Laboratory Lecture in Room 302
Office Number: Byrd Hall room 401
Office Hours: If you have difficulty with course concepts or have any questions, please feel free to drop by for help. If my office hours do not coincide with your free time, then schedule an appointment. 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 having the opportunity to interject questions. This method makes better use of everyone's time.
- M, W, Th 1-2 pm
- F 11 am - 12 pm
Phone Number: 953-7788
Email Address: mabrouks@citadel.edu
If you need help at night, the best way to reach me is via email.

General Course Information

Required Text:
- Experimental Organic Chemistry: A Miniscale & Microscale Approach by Gilbert & Martin, 4th ed.

Course Prerequisites:
- Chem 151, 152, 161, 162, 207 and 217
- Each student should know how to work safely in the chemistry lab. Each student should recall the various organic lab techniques taught in Chem 217 (simple and fractional distillation, extraction, recrystallization, and melting point) and the chemistry taught in Chem 207.
Co-requisite: Chem 208

Course Content: Using techniques from Chem 217 and reactions from Chem 207 and 208, students will gain experience in the synthesis of various functionalized organic compounds. The preparation and isolation of all compounds will be verified using bp, chemical tests, GC, IR, mp, and refractometry, where applicable. Following the completion of this course, each student will be at ease in the organic laboratory, in order to synthesize and to characterize organic compounds.

Course Objective: By the end of this lab course, students will be able:
1. to synthesize organic compounds and
2. to characterize these same compounds via chemical tests and other analyses.

Laboratory Lectures
- All lectures have been posted to Blackboard (Bb). 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 on Thursdays so that the notes can be annotated during the lecture.
Electronic devices: PDAs and laptop computers are allowed in the classroom for note taking. Cell phones must be set on vibrate. Only calculators may be used during a quiz. The calculator may ne be pre-programmed with formulas. No other electronic devices may be used or in view during a quiz.

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!

Quizzes: There will be four total quizzes, the lowest of which will be dropped at the end of the course. The quizzes will occur as indicated on the lab schedule. They will address the main and any side reactions, mechanism(s), chemical test reactions, and the techniques employed on the two experiments conducted recently. Students should understand why they perform each step in a procedure. Make-up quizzess will only be given to students who have missed the lab or quiz for a legitimate reason (family emergency or personal illness). The quiz average will constitute 60% of the final course grade.

Final Exam: There is no final exam in this course.

Data Sheets: Students, working in pairs, will submit one data sheet for the pair the day after completing the experiment. Students will write these sheets independently of other classmates. Data sheets will not be accepted late. At the end of the semester, the lowest data sheet will be dropped. The average of the remaining data sheets will constitute 40% of the final course grade.

Lab Duty: Each lab day, each student will sign-up for a specific duty (listed on side wall near entrance) in the lab room. This task must be performed following completion of the experiment and before leaving lab. The student must then have that task and their lab bench checked by the professor before leaving lab. Until the professor approves the work, the student may not leave lab. After receiving approval from the professor, the student must then sign the log book, indicating that the student has left the premises.

Final Course Grade: Since people have a bad day periodically, one quiz and one data sheet will be dropped at the end of the course.
- Use the following equation to determine your final course grade.
  - Final Course Grade = (Quiz Avg)(0.60) + (Lab Report Avg)(0.40)
- Quiz average (minus two lowest): 60%
- Lab Report average (minus two lowest): 40%
Scale for Final Course Grades: All lab grades are awarded based on the following fixed scale.
- 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.

Laboratory Attendance and Etiquette (labconduct.htm)

Attendance at each lab is mandatory, as described in the college catalog p. 25. Failure to be present in lab without a reasonable excuse will result in a grade of 0 on that day's quiz and the associated lab report. A missed lab can only be made up at the instructors approval, where the student has a legitimate excuse (family emergency or personal illness).
- 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.
Students should not speak while the professor or a classmate is speaking.
Students should speak respectfuilly to the professor and all classmates.
When a student has a question, the student should raise their 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.
Food, drink, smoking, and tobacco are prohibited in Byrd Hall.
The use of profane language is unacceptable in the presence of this professor.

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 218 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 Bb 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 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 Etiquette

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.
Students must 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.
Students must print and sign their 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.
Students are prohibited from discussing the quiz with any Chem 218 student who has not already taken the quiz. Discussions include any information pertaining to a quiz that a student would not have before taking it. These discussions include the difficulty level and the content.
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
July 6	Syllabus and Lab Lectures for Week
July 7	Nitration of Methyl Benzoate and Hydroxide Test for Nitro Compounds.	Pavia, D.; Kriz, G. S.; Lampman, G. M.; and Engel, R. G. Introduction to Organic Laboratory Techniques: A Small Scale Approach; Saunders: Philadelphia, 1998; pp. 297-300. Section 25.15 (pp. 879-880). Sections 2.5-2.7, 2.15, and Chapter 3. MSDS of nitric and sulfuric acids.
July 8	Preparation of Opaque Soap	Handout MSDS of sodium hydroxide.
July 9	Bromination of Acetanilide	Schatz, P. F. J. Chem. Educ. 1996, 73, 267. Sections 2.5-2.7, 2.15, and Chapter 3. MSDS of glacial acetic acid and hydrobromic acid.
July 10	Quiz and Lab Lectures for following week
July 14	Parallel Combinatorial Synthesis of Azo Dyes.	Gung, B. W.; Taylor, R. T. J. Chem. Educ. 2004, 81, 1630-1632. Sections 2.5-2.6, 2.9-2.11, and 2.17. MSDS of 4-aminobenzenesulfonic acid (sulfanilic acid), salicylic acid, sodium nitrite, hydrochloric acid, and sodium hydroxide.
July 15	Reduction of 9-Fluorenone	pp. 569-71. MSDS of 9-fluorenone, methanol, sodium borohydride, & sulfuric acid.
July 16	Aldehydes and Ketones: Semicarbazones, Iodoform, and Tollens' Test.	p. 844 and pp. 848-49. MSDS of acetone, ammonia, benzaldehyde, iodine, silver nitrate, sodium hydroxide.
July 17	Quiz and Lab Lectures for following week
July 21	Synthesis of trans-p-Anisalacetophenone and Baeyer Test	pp. 601-4. Sections 2.9-2.11, 2.17, & 24.8B. MSDS of acetophenone, p-anisaldehyde, ethanol, & sodium hydroxide.
July 22	Preparation of Benzocaine	pp. 651-6. Sections 2.9-2.11, 2.17, & 2.22. MSDS of p-aminobenzoic acid, ethanol, & sulfuric acid.
July 23	Preparation of Aspirin and pH and Sodium Bicarbonate Test for Carboxylic Acids.	Pavia, D.; Kriz, G. S.; Lampman, G. M.; and Engel, R. G. Introduction to Organic Laboratory Techniques: A Small Scale Approach; Saunders: Philadelphia, 1998; pp. 46-56 & pp. 514-515. Sections 2.5-2.6, 2.9-2.11, 2.17, and Chapter 3. MSDS of salicylic acid, sulfuric acid, and acetic anhydride
July 24	Quiz and Lab Lectures for following week
July 28	Preparation of Acetanilide	pp. 691-2 & 695-6 & handout. Sections 2.9-2.11, 2.17, & 2.26. MSDS of acetic anhydride, aniline, & hydrochloric acid.
July 29	Classification Tests of Carbohydrates (hydrolyzed sucrose, sucrose, glucose, fructose, honey, splenda, aspartame)	pp. 778-80. Sections 2.9 & 2.17. MSDS of ammonia, silver nitrate, & sodium hydroxide.
July 30	Completion of Opaque Soap.	Handout MSDS of sodium hydroxide.
July 31	Last Quiz, Evaluations, and Check-out.

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 Bb.
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 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.