Syllabus Chem 29A, Organic Chemistry Laboratory

V. Cornel, Reedley College, Fall 2010, #57074

 

Lab TTh 8:00-10:50 pm in PHY-77

Office: PHY-78, phone # 559-638-3641 ext 3449

email: vmcornel@scccd.org  using “CHEM29” or “O-chem”as the subject

Office hours: 10-11am MWF

Course web site: blackboard.reedleycollege.edu

Course corequisite: Chem 28A 

Textbooks:

1.      Svoronos/Sarlo, Organic Chemistry Laboratory Manual, 2nd edition.

2.      McMurray: Organic Chemistry. A Biological Approach. 2nd edition

 

Required Materials:

  1. A lab research notebook or notebook. 
  2. Safety glasses with Z-87 safety code 
  3. A lab coat or apron. 
  4. Box of latex gloves (or latex-free, powder free)

 

Course objectives and outcomes: Students will become familiar with safety procedures and lab equipment for semi-micro organic experiments.  They will be capable of synthesizing and purifying organic compounds, of measuring melting points, refractive index, and optical activity.  They will learn hands-on how to work with a Gas Chromatograph Mass Spectrometer, a Fourier Transform Infrared Spectrophotometer and Nuclear Magenetic Resonance Spectrometer.  Extensive time will be spent on identification of unknown compounds by analyzing their MS, IR and NMR spectra.  Through interactive computer programs the students will receive extensive support in thoroughly understanding the concepts taught in the organic chemistry lecture (Chem 28A).

Homework: Students are expected to come to lab well prepared.  This means that the steps to be taken to properly complete the experiment are written down in the lab notebook ahead of time.  Typically, the theoretical explanations in the lab manual are too brief to fully comprehend the experiment.  Therefore preparation reading McMurray's text on the subject is highly recommended. 

Lab reports: Your lab notebook needs to be complete at all times and could be requested by the university you are transferring to.  The Aim, Method, Reaction Mechanism, Physical Data (melting point, refractive index etc.), Observations, Percent Yield, and Conclusion should all be recorded. Certain questions at the end of each lab also need to be completed using your textbook. I will give assistance, but not the answers to the questions. The lab report (including answers to the questions) or a good photocopy of it needs to be handed in within one week of the class completing the experiment.

This semester three experiments are finalized with a formal lab report using the observations and data collected in the experiment.  The extensive lab reports are a write-up of the experiment, and written in the format of a research paper with an abstract (summary) and references.  The student will need to use resources in the library and the internet to find appropriate theoretical background information.  An electronic copy of the abstract and background needs to be e-mailed to the instructor, and a printed copy of the report must be submitted to the instructor or switchboard by the due dates in the lab schedule. Lab reports will be checked for plagiarism using “Turnitin”.

Lab materials: Expensive grounded glassware and other delicate lab supplies will be made available.  Students will be held responsible for their own desk inventory. 

Attendance: Attendance at all labs is mandatory.  In accordance with Community College policy role will be taken every lab session.  Students will only be allowed to drop one laboratory assignment (and not one that is used for a Formal Report).  You will be dropped if you miss two weeks before the drop date without contacting the instructor. 

Cancelled Classes: If the instructor is absent, and official yellow “class cancellation” notice and instructions will be posted on the door of the classroom. We will try and put a timely announcement on Blackboard and the Reedley College website.

 

Make-up labs If you have to miss a lab you may be able to make arrangements with the instructor or lab technician to complete it (if the chemicals are still available), or complete it the next lab period.  10% will be deducted for the inconvenience of having to do a make-up lab for the student.  A maximum of two make-up labs will be allowed per student.  If you do not complete an experiment (drying, purifying your product or analyzing it) you may be able to make arrangements with the instructor or lab technician to complete it (with no points deducted).

Grading: To determine the final grade in this class the average of the formal reports will count towards 30%, and the individually graded labs towards 70% of your final grade.  In addition, I will also take into account the quality and the yield of the product, the working technique and effort, the amount of assistance the student required and the efforts to reach the experimental goal.  General grade break-off : A 90% and up; B 80-89%; C 70-79%; D 60-69%; F 59% and lower. 

Drop date: The drop date is Friday October 15, 2010.  After this date a letter grade A-F will have to appear on your transcripts.  If you are dropped from the class before Friday September 3, 2010 you avoid receiving a W. 

Lab rules: It is MANDATORY to use a lab coat and safety glasses at any time that you are in the lab.  You are required to have read each experiment, including the Safety Tips before you enter the lab.  The Aim and Method needs to be written out before you enter the lab and will be checked.  You will receive safety instructions on how to perform the experiment.  It is imperative that you not be late in lab, you would be a hazard to others if you miss the safety instructions.  Coming in late means you loose 10% for that lab.  You need to go over the safety instructions with the instructor before you may start the lab. End lab time is set: 10:50 am sharp.  

Copying of experimental data and answers to questions in lab reports is considered fraudulent behavior and will result in a zero grade for the copier and the originator. 

Important: If you have a verified need for an academic accommodation or materials in alternate media (i.e., Braille, large print, electronic text, etc.) per the Americans with Disabilities Act (ADA) or Section 504 of the Rehabilitation Act, please contact me as soon as possible.

 

CHEM29A Fall 2010 T/Th

 

Date

Lab

1  

Aug 17

Read Preface and pages 1-3. Lab safety quiz. Get familiar with MSDS sheets. 

 

Aug 19

Practice Lewis Structures, molecular modeling and chemical bonds

2  

Aug 24

Molecular Orbital lab (handout). Read McMurray Chapter 1.

  

Aug 26

Exp 3.1 C Melting Point Determination. Read Ch. 3 pgs 19-21.

Exp. 3.3 Refractive Index (using digital RI). Read pgs 26-28

3    

Aug 31

Exp. 4.1 parts I and II. Simple Distillations. Read pgs 29-31 thoroughly.

    

Sep 2

Exp. 4.2 Fractional Distillation.

4   

Sep 7

Exp. 6.2 Extraction. Read pgs 54-56

 

Sep 9

Exp. 6.3 Re-crystallization. Read pgs 66-69

5

Sep 14

Exp. 6.5 Isolation of Caffeine from Tea

 

Sep 16

Chapter 2.1 and 2.2 Stereochemistry and Molecular models.

6

Sep 21

Chapter 2: Stereochemistry in more depth: the R/S designation, Fischer projection formulas and meso-compounds. Read McMurray Ch 9 and assigned problems.

 

Sep 23

Exp. 7 Equilibrium constant. Read Ch. 7 pgs 78-79.

7

Sep 28

Exp. 8 Sodium Fusion Test. Read Ch. 8 pg 83

 

Sep 30

Exp. 10.1 Synthesis of Cyclohexane. Read Ch. 10 pgs 123-125.

8

Oct 5

Exp. 10.4 Oxidation of Cyclohexene to Adipic Acid

 

Oct 7

CHEMDRAW exercises – to be used for Formal report

9   

Oct 12

Work on Formal Report 1:  10.4 Oxidation of Cyclohexene   Due Oct 19  

    

Oct 14

Exp. 11 Synthesis and Reactions of Acetylene and the Qualitative Tests of Hydrocarbons and Alkyl Halides. Read Ch. 11 pgs 141-142.

 

Oct 15

Drop Date. Last day to drop class. After this date a grade will be given.

10

Oct 19

Exp. 15.2 Friedel-Crafts Alkylation: A Microscale Synthesis. Read pgs 192-193

 

Oct 21

Exp. 13.1 The Synthesis of t-Butyl Chloride. Read Ch.13 pg 151

11

Oct 26

Exp. 13.2 The Solvolysis of t-Butyl Chloride. Read Ch 13 pgs 154-156.

Exp. 14.2 Qualitative tests for Alcohols. Read Ch 14 pgs 180-183

 

Oct 28

Exp. 14.3 Preparation of Phenacetin from Acetaminophen. Read pgs 185-187.

12

Nov 2

Work on Formal Report 2: 13.1 The Synthesis of t-Butyl Chloride Due Nov 9

 

Nov 4

Introduction to Infrared Spectroscopy. Read Chapter 9.1 pgs 89-92

Analysing samples using the Infrared Spectrometer. Dry glassware for 14.1

13 

Nov 9

Exp 14.1 Alcohols. The Grignard Reaction. Read Ch. 14 pgs 175-177.

 

Nov 11

Exp 14.1 cont.

14 

Nov 16

Work on Formal Report 3:  Grignard Rxn Due Nov 23

 

Nov 18

Introduction to Mass Spectroscopy (handout).

15

Nov 23

Analysing samples using the Gas Chromatography Mass Spectrometer

 

Nov 25-6

Thanksgiving Holiday

16

Nov 30

Introduction to NMR. Read McMurray 12.1-3, 8-11  Lab 9: Q1,2,9

 

Dec 2

Analysis of unknown compounds by combination of MS, IR and NMR.

17

Dec 7

Nomenclature and Functional Group check

 

Dec 9

Analysis of unknown compounds by combination of MS, IR and NMR

 

 

Student Learning Outcomes:

 

1.  read and follow instructions in an organic laboratory manual, safely handling organic chemicals and glassware with ground-glass joints.
   2. determine physical properties of organic compounds such as melting point and refractive index.
   3. synthesize simple organic compounds such as but not limited to cyclohexene, t-butylchloride, alcohols and acids.
   4. analyze organic molecules using a gas chromatograph and infrared spectrometer and interpret the spectra.

5. write three formal laboratory reports in the form of research papers.

 

Lab Content:

Each of the following experiments will take 4-6 hours. Alternative experiments may be substituted.
A. Laboratory safety

B. Physical Properties

C. Distillation

D. Extraction and recrystallization

E. Alkenes and alkynes

F. The sodium fusion test

G. Alkyl halides and the nucleophilic aliphatic substitution

H. Equilibrium constant

I. Alcohols

J. Spectroscopy

K. Stereochemistry