COURSE OUTLINE

GENERAL INFORMATION

Textbook: Organic Chemistry, Carey, 4th Edition (McGraw-Hill, 2000).

Laboratory Text: Experimental Organic Chemistry, Gilbert & Martin, 2nd Edition Saunders College Publishing (1998)

Supplements: 1. Study guide and solutions manual for Carey

2. Laboratory notebook

3. Molecular models (optional)

4. Safety glasses

Attendance:

The maximum allowable absences are twice the number of class meetings per week (lecture or lab). Students adding courses after classes

begin are responsible for work covered from the first day of class. All classes missed are counted as absences.

Grades

There will be five lecture tests to determine student competency. The final exam will be a retest of an unsatisfactory test outcome, at the option of the student. The average of Laboratory performance and notebook comprise 25% of the grade.

A: 90-100, B: 80-89, C: 70-79, D: 60-69, F below 60

Course Objectives:

Study guides will be provided, which will give the objectives and proficiencies to be tested on each test.

Department Chair Statement:

The science department chair, coordinators, and faculty are here to help you. If you are having any problems in your classes, please contact the people who can help you. If we don’t know you are having problems, we can’t help you. (Dr. Perry Carter 822-3443, Department Chair, Dr. Gerry Lopez, Airport Coordinator 822-3788, Dr. Bert Knesel, Beltline Coordinator 738-7660).

Disabilities Statement:

Students with disabilities requiring in-class accommodations should call the Counseling/Disabilities Resource Center at 738-7636.

LABORATORY NOTEBOOK FORMAT

Refer to section 1.2 (pages 4-14) of your laboratory textbook.

Early in the semester, use the investigative format as given below.

For dehydrohalogenation (10.2) and preparation of 1-bromobutane (14.4) use the preparative format as given below.

Start each experiment on a new page. Write in ink (do not erase; cross out mistakes) and write only on the front side of a page. Write the date of the experiment and cite the section of the textbook used. Do not tear out pages in the notebook. Simply X out any pages that are to be ignored. Tape gas chromatographs and IR spectra into notebook.

Investigative Format

1. Title

2. Introduction (as described in your text)

3. Table of chemicals used (Headings: name, molecular formula/MW, density, melting point or boiling point, solubility in water)

4. Experimental procedure (synopsis in step form)

5. Observations (the heart of your notebook, be prolific) (includes data and sensory observations, e.g. color change, foaming, knocked over flask)

6. Calculations

7. Discussion of results

Preparative Format

1. Title, introduction

2. Balanced chemical equation (not mechanism)

3. Chemical equation(s) for important side reaction(s)

4. Table of chemicals (reactants, products, catalysts, solvents) (same headings as above)

5. Experimental procedure (synopsis in step form)

6. Observations (Record the actual amount, both weight and mmoles, of reagents used)

7. Calculation of theoretical and percent yields

8. Discussion of results

Properties for the “Table of Chemicals” can be obtained from the CRC Handbook of Chemistry and Physics, which is in the MTC library. The Merck Index will also have many of the chemicals used.

You may also use the Internet to obtain these properties. This is often the easiest way since this resource recognizes any of the correct names for a compound. The Internet address is: http://chemfinder.com.

CHM 211 Laboratory Schedule

Week Experiment

First Introduction, Chapter 1, Bench Assignments, Safety, Notebooks, % Yield

Second Recrystallization procedures, Sec 2.17, 3.2. Recrystallization of impure acetanilie (p 98-99). Add 20 ml of water initially to dissolve crude acetanilide. Omit paragraphs 2 & 3 on p 99. No filter aid needed.

Third Melting point determinations, Sec 2.7 & 3.3. Use Thiele tube and burner to obtain melting points.

Fourth Distillation theory (sec 4.1-4.4) (2.13-2.16)

Fractional Distillation of a Binary Mixture (p 129)

Use 25 ml of ethyl acetate and 15 ml of n-butyl acetate in a 100 ml round bottom flask. Stop distillation when overhead temperature reaches 123⁰C.

Fifth 6.4 – Gas Chromatography: Instruction and Analysis of Distillation cuts.

Sixth 8.2 – Infrared Spectroscopy: Instruction and Demonstration

Seventh 6.2: Handout – Thin Layer Chromatography of Analgesic Drugs

Eighth 8.3 & Ch 13 in Carey – NMR (Nuclear Magnetic Resonance Spectroscopy): Instruction and Interpretation of Spectra

Ninth 10.2A – Dehydrohalogenation of 2 – bromo-2-methylbutane with potassium

Tenth hyrodxide, (pp 314-315). Add 5.6 g KOH in 25 mL 1-propanol. Column packing not necessary. Reflux for 1 hr. GC and BR2 test. No Baeyer test or IR spectrum.

Eleventh 9.3 – Bromination: Selectivity (pp 303-4) Use only one set of test tubes.

Twenty minutes at room temperature, then light bulb. No IR spectra.

Twelfth 14.4 – Preparation of 1-bromobutane (pp 429-430) (Sec 2.21 Extraction)

Thirteenth Use 26.0g NaBr, 20.0mL of 1-butanol and 40 mL of 8M H₂SO₄. Use your magnetic stirrer. Skip simple distillation. Instead add 20 ml of water to the reaction mixture and separate the phases using the separatory funnel. Then do the washings of the organic phase as follows. First wash with 10 ml of water, then 10 ml conc. H₂SO₄, then 10 ml 1 M NaOH, then 10ml of sat’d salt solution. Use boiling stones, not magnetic stirrer for distillation. Analysis: %Yield, gc, IR of product.

Fourteenth Finish any uncompleted work and clean up equipment.

COURSE OUTLINE

MIDLANDS TECHNICAL COLLEGE

GENERAL INFORMATION

The maximum allowable absences are twice the number of class meetings per week (lecture or lab). Students adding courses after classes

begin are responsible for work covered from the first day of class. All classes missed are counted as absences.

Preparative Format