6/11/14 DATE x REQUIRED COURSE
ELECTIVE COURSE x
DIVISION
NEW COURSE
REVISION
COURSE NUMBER CHM 253 TITLE Organic Chemistry Laboratory 1
SEM CR HRS 1.00 LT HRS 0.00 LAB HRS 3.00 SOE HRS
COURSE PCS#
ECH
(Assigned by Administration)
Prerequisites: CHM 151
Catalog Description (40 Word Limit): Laboratory course introduces synthesis and the basic techniques for the separation, isolation, purification and identification of organic compounds. To be taken concurrently with CHM 243.
List the Major Course Objectives (Units) Contact Lt Hrs Contact Lab Hrs
Equipment and Safety Introduction
Separation Techniques Based on Physical Properties
Reaction and product purification
Distillation
Nucleophilic Substitution
Elimination
Addition
Borohydride Reduction
Spectroscopy
Rearrangements
Quizzes x Exams x Oral Pres. Papers
3
3
3
9
3
3
6
3
6
6
Lab Work x Projects Comp Final
Textbook : Title : Operational Organic Chemistry
Author : John W. Lehman
Publisher : Pearson / Prentice Hall
Volume/Edition
Copyright Date
:
:
4th
2009 x Other

LAB CONTENT
Listed below are the experiments completed in this course.
Students are required to maintain a laboratory notebook in which they must include:
1. Pre-lab assignments including quantities of reactants required, the theoretical yield of product, reactions, mechanisms, and procedures.
2. Observations Raw Data and Calculations
3. Results
4. Conclusions related to the problem and an explanation of how one arrived at these conclusions.
EXPERIMENTS: Some of these experiments require more than one three hour lab period and are continued the following week.
1. Separating and identifying the components of Panacetin . Students learn the techniques of extraction, roto-evaporation, and melting point determination. Equipment used: electronic balance, separatory funnel, Buchner funnel, filter flaskround bottom flask, Erlenmeyer flask, filter paper, rotary evaporator, melting point apparatus.
2. Synthesis of salicylic acid from wintergreen oil.
Students complete a short organic reaction, and then learn the technique of re-crystallization. Equipment used: heating mantle and variac, round bottom flask, reflux condenser, graduated cylinder, electronic balance, pH paper, Buchner funnel, filter flask, melting point apparatus.
3. Preparaton, purification and analysis of Banana Oil.
Students utilize the Fisher
Esterification to prepare banana oil. They are then introduced to the technique of distillation.
Equipment used: graduated cylinder, electronic balance, round bottom flask, reflux condensers, thermometer adaptor, thermometer, 3-way adaptor, vacuum adapter, heating mantle, and variac.
4. Preparation of methylcyclohexenes.
Students are exposed to elimination reactions. The products are identified by monitoring the key functional group transformation using IR spectroscopy. Equipment used: graduated cylinder, electronic balance, round bottom flask, reflux condenser, three way adapter, vacuum adapter, variac, heating mantle, thermometer adapter, thermometer, separatory funnel, pipets, IR spectrometer.
5. Preparation of n-bromobutane or 2-bromobutane.
Students are exposed to both S n
1 and
S n
2 reactions through this experiment. A comparison of yields and reaction times is made.
Products are verified using IR spectroscopy. Equipment used: graduated cylinder, electronic balance, round bottom flask, reflux condenser, three way adapter, thermometer adapter, thermometer, vacuum adapter, pipets, variac, heating mantle, separatory funnel, NMR and IR spectrometers.

6. Identify an unknown product from a rearrangement.
Students carry out a Pinacol rearrangement (unaware that it will occur). Spectral data will be used to identify the unexpected product. Equipment used: electronic balance, graduated cylinder, round bottom flask, three way adapter, separatory funnel, Erlenmeyer flask, NMR spectrometer, IR spectrometer.
7. Bromine addition to cinnamic acid.
Exposure to addition reactions is gained. Product is identified by proton NMR and IR. Stereochemistry of addition is identified using melting point data. Equipment used: graduated cylinder, electronic balance, round bottom flask, Claisen adapter, addition funnel, magnetic stir bar, Erlenmeyer flask, Buchner funnel, filter flask, melting point apparatus, IR spectrometer, NMR spectrometer.
8. NMR and IR Spectroscopy.
Students identify two unknowns: 1. Using traditional derivative synthesis (qualitative analysis) and 2. Using NMR and IR spectroscopy. Equipment used: test tubes, pipets, TLC plates, Hirsch funnel, vacuum flask, NMR spectrometer, IR spectrometer, melting point apparatus.
9. Microwave Assisted Reactions.
Students re-do the preparation of banana oil using a
microwave to gain an appreciation for the technique. They will also carry out the hydration of
an alkene to produce a ketone. Confirmation of success is based on IR and NMR spectral
data. Equipment used: Electronic balance, pipets, microwave reaction tube, magnetic stir bar,
microwave reactor, separatory funnel, Erlenmeyer flask, NMR and IR spectrometers

Major Course Objectives
Equipment and Safety
Panacetin Separation
Solubility
Acid Base Properties
Melting Point
Salicylic Acid Preparation
Recrystallization
Melting Point
Distillation
Nucleophilic Substitution
Elimination
Rearrangements
Addition
Spectroscopy
Microwave Reactions
Hours
3
3
3
6
3
3
3
3
12
6
Learning Outcomes
Student will be able to:
Identify various types of equipment and glassware used in an organic laboratory. Assemble and operate equipment for carrying out experimental techniques. Understand lab safety
Separate organic materials based on solubility in organic solvents and acid base properties of molecules. Purify separated components. Obtain melting points.
Learn how to carry out and monitor a reflux. Separate and purify the product.
Learn to purify a product through the use of distillation.
Compare the techniques of fractional and simple distillation.
Understand the pros and cons of each method.
Recognize the differences between primary and secondary starting materials. Purify product by distillation. Identify progress of reactions by using IR spectroscopy.
Understand how Le Chateliers Principle affects equilibrium.
Monitor reaction progress through IR spectroscopy.
Expand on earlier elimination knowledge by understanding E1 vs E2 pathways and the propensity for molecular rearrangements to occur.
Learn how to add sensitive reagents through an addition funnel. Monitor the reaction using IR spectroscopy.
Learn the art of spectral interpretation as it applies to mass spectrometry, UV-Vis, IR, and NMR. Learn how to operate
NMR and IR spectrometers. Use NMR and IR to identify the structure of several unknowns. Compare results to those obtained through traditional qualitative analysis methods.
Carry out an esterification and an alkyne hydration in a microwave. Learn about the advantages of microwave synthesis.

Course Outcomes: At the successful completion of this course, students will be able to:

Learn basic lab techniques such as reflux, distillation, recrystallization, extraction, and separation of organic molecules.
 Learn to keep a detailed “research style” lab notebook.

Learn how to report lab results to a group.

Learn how to monitor a reaction, isolate a product, and characterize the product.

Gain a fundamental understanding of modern organic spectroscopic techniques (NMR, IR, mass spectrometry) through both the interpretation and acquisition of spectra.