Introductory Organic Chemistry Laboratory (CHM 361)



Introductory Organic Chemistry Laboratory (CHM 361): Spring 2008

Credit: 3 hours Prerequisite or Co-requisite: CHM 356

Instructor: Dr. John L. Hubbard, Science 484, 696-3136, hubbard@marshall.edu

Office Hours (subject to change): TR 12-2; W 2-4; or by appointment

Required text: Pavia et al., Introduction to Organic Laboratory Techniques: A Microscale Approach, 4th ed.

Other required items: eye protection, bound laboratory notebook, paper towels, lock

Recommended: laboratory coat or apron

Mandatory Safety Training: Go to . It must be completed and the safety quiz must be passed before working in the laboratory is permitted (i.e., before 1/21). [NOTE: This is not required if it was done during fall semester 2007.]

COURSE SCHEDULE

1/15 Introduction, Safety, Calculations, Notebook, Check-In. Read pp 542-580.

1/17 Safety Quiz. Techniques, Instrumentation.

Exp 1 Introduction to Microscale Laboratory. Lab Exercises 1A, 2.

Exp 3A Crystallization. T 8-11. Q (p 32) 1-3.

1/22 Exp 14A Oil of Cloves (part 1). T 5-7, 12, 18, 25. Q (p 116) 1-3. Read pp 108-116.

1/24 Exp 14A (part 2). Exp 45 Benzocaine (part 10. T 8-11. Q (p 373) 2-5. Read pp 367-373.

1/29 Exp 45 (part 2).

1/31 Exp 28 Nitration of Methyl Benzoate. T 11. Q (p 232) 1-3, 5.

2/5 Exp 25A 4-Methylcyclohexene (part 1). T 5, 6, 12, 13, 14, 25. Q (p 216-217) 1-3, 5.

2/7 Exp 25A (part 2). Exp 66 An Oxidation Puzzle (part 1). T 12, 25.

2/12 Exp 66 (part 2). Prepare equipment for Exp 38A.

2/14 Exp 38A Triphenylmethanol (part 1). T 4, 5, 7. Q (p 327) 1, 2, 5.

2/19 Exp 38A (part 2). Begin Exp 36A Preparation of Benzoin by Thiamine Catalysis.

2/21 Exp 35B Reduction of Camphor to Isoborneol. T 6-9, 12. Q (p 301) 1-3.

2/26 MIDTERM EXAM. Exp 36A Preparation of Benzoin by Thiamine Catalysis. T 6-9, 11, 12.

Q (pp 308-309) 1, 4. [Note: same techniques apply to Exp 36B and 36C.]

2/28 Exp 36B Benzil.

3/4 Exp 36C Benzilic Acid. Q (p 314) 1, 2.

3/6 Exp 44C 1,4-Diphenyl-1,3-butadiene. T 8. Q (p 366) 1, 2, 4.

3/11 Exp 42 Preparation of an α,β-Unsaturated Ketone via Michael and Aldol Condensation

Reactions (part 1). T 7, 8, 11, 12. Q (p 347) 1-4.

3/13 Exp 42 (part 2).

3/18 Lecture I Identification of Organic Compounds (ID of OC). Read pp 448-494, 971-975.

Neutral Unknown (begin).

3/20 Lecture II ID of OC. Neutral Unknown (continue).

4/1, 3 Lecture III ID of OC. Neutral Unknown (continue).

4/8, 10, 15 General Unknown I.

4/17, 22, 24 General Unknown II.

4/29 Catchup. Cleanup. Check-Out if ready.

5/1 Last Report Due. Cleanup. Check-Out.

5/8 FINAL EXAM (12:45-2:45 pm)

Completion of all Experiments and Exams is Required; Attendance is Required. For policy concerning excused absences, see the online catalog, p 121 at ; however, bear in mind that excessive absences of any type are difficult to accommodate in a laboratory course.

Electronic Devices: Cellular telephones and other electronic devices must be turned off during class. This means from 2:00 pm until you have finished work and left the laboratory for the day.

Calculators: Use of electronic calculators during quizzes or exams is not permitted.

Disability: Accommodations may be granted for certain learning disabilities if the required notice is received via campus mail from either the HELP Center (Myers Hall) or Sandra Clements (PH 117). It is the responsibility of the student to request this notice and to meet with the instructor in advance to make any necessary arrangements.

Course Performance: Except in highly unusual circumstances, no make-up of experiments or quizzes is permitted. Missed quizzes or experiments are considered “lowest”. The lowest quiz and report scores will be dropped so that an unavoidable absence will not jeopardize one’s grade.

Computation of final numerical grades: Products/Reports 25%, Quizzes 25%, Mid-term Exam 20%, Final Exam 25%, Instructor Evaluation 5%. Instructor Evaluation is diminished by the following:

1. Excessive breakage of glassware; loss of or damage to equipment.

2. Improper maintenance of work areas.

3. Leaving hotplate on.

4. Violation of safety rules (repeated violations are grounds for expulsion).

5. Improper keeping of notebook.

6. Repeated and obvious lack of preparedness, including consistent poor performance on quizzes/exams.

Final letter grades of A, B, C, or D will be assigned for numerical percentages 90-100, 80-89, 70-79, or 60-69, respectively.

Notebooks are subject to inspection at any time. Lab reports (with products, if applicable) are submitted by 2:00 pm the second period after completion of the experiment (last day for experiment indicated in the course schedule): late reports are not accepted.

Quizzes are indeterminate in number and unannounced. They will occur in the first ten minutes of the laboratory period. Questions may concern any material previously covered as well as the subject of the day.

Suggestions

1. Success requires adequate preparation before arriving in the laboratory. Read all pertinent material.

2. Fatigue, lack of nourishment, or illness lead to difficulties. Get adequate rest the previous night and eat lunch before coming to the laboratory. Do not attempt laboratory work if symptoms such as nausea or fever are exhibited.

3. To avoid mishaps, be deliberate. Efficiency and productivity are best achieved without undue haste. Think before acting.

4. Mastery of chemistry and techniques so that one is able to do more than just follow a recipe step by step is necessary for a satisfactory laboratory experience. Laboratory work is art as well as science.

Learning Objectives: (1) Know the safety rules and procedures followed in the laboratory. (2) Know the location of all safety equipment in the laboratory room and be able to operate it if necessary. (3) Learn the proper manner of keeping a laboratory notebook. (4) Learn the techniques necessary for carrying out organic reactions. (5) Know the reactions performed in the various experiments and be able to write complete equations for these and similar reactions. (6) Understand the process for identification of unknown compounds.

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