Republic of the Philippines
BICOL UNIVERSITY
Legazpi City
COLLEGE OF SCIENCE
Department of Chemistry
COURSE INFORMATION
I.
Course Code:
Course Title:
Prerequisite:
Term:
School Year:
Instructor:
Website:
E-mail:
CHEM 33
Organic Analysis (Lecture and Laboratory)
CHEM 33
1st Semester
2009-2010
MICHAEL V. MONTEALEGRE
buchem.weebly.com
mvmnt2@yahoo.com
II.
Course Description:
Organic Analysis covers spectroscopic techniques used commonly in the structure
elucidation of organic compounds. Spectroscopic methods include Mass
Spectrometry, Infrared spectroscopy, UV/Vis spectroscopy, and 1H and 13C NMR
Spectroscopy. The course also includes the qualitative organic analysis.
Accompanying lab course complements the lecture with exercises given the
spectra of simple organic compounds.
III.
IV.
Course Duration:
3A
Schedule
3B
Credit Units:
V.
Placement
Lecture
54 hours
Tuesday, Thursday 9:00-10:30 AM
Tuesday, Thursday 1:00-2:30 PM
3 units Lecture
Laboratory
108 hours
Friday 7AM-1PM
Friday 1PM-7PM
2 units Laboratory
BS Chemistry
VI. COURSE OBJECTIVES
At the end of the semester, the students must be able to:
1.
Review important concepts in organic chemistry such as nomenclature, physical and chemical
properties and separation techniques in the laboratory,
2.
Learn the theories and principles of the different spectroscopic techniques (MS, UV/Vis, IR, NMR),
3.
Understand the principles of spectroscopy including instrumentation, spectroscopic processes,
4.
Interpret and analyze spectra of the different techniques for a simple organic compound;
5.
Predict structure of unknown organic compound based on the given properties and spectra.
Content
PRELIMINARIES
VMGO of the University, College
of Science, Department of
Chemistry
REVIEW
I. IUPAC Nomenclature of
different functional groups
II. Physical Properties
III. Chemical Properties
IV. Separation Techniques
ORGANIC QUALITATIVE
ANALYSIS
I. Classification of Organic
Compounds by Solubility
A. Determination of
Solubilities
B. General Solubility Rules
C. Solubility in Organic
Solvents
II. Chemical Tests for
Functional Groups
Specific Objectives
Relate the mission, vision and goals of the
college to the role of chemistry in the
realization of these VMGO
Schedule/
hrs
Activities/Methodologies/
Teaching Strategies
1.5
The student should be able to:
1. Recall basic organic nomenclature
2. Enumerate and describe the physical
properties of organic compounds
3. Identify chemical reactions with visible
changes in the solution
4. Determine separation technique for
mixture of organic compounds
5. Familiarize with the use of ACD
Chemsketch to draw organic compounds
4.5(lec)
18(lab)
The student should be able to:
1. Review solubility trend among the
different functional groups;
2. Classify organic compounds according to
their solubility property;
3. Identify chemical tests for specific
functional groups;
4. Suggest chemical tests appropriate for
specific organic compounds;
5. Propose scheme in identifying simple
organic compounds using chemical tests
and known properties;
6. Identify unknown organic compounds
based on the given properties and results
from chemical tests.
6(lec)
12(lab)
Materials
Evaluation/
Assessment
Technique
VMGO
handout/transparencies
Lecture
Board Work
Problem Sets
Lab activities:
 Exercises:
nomenclature, physical
and chemical properties
 Computer – use of
chemsketch software
Lecture
Board Work
Problem Sets
Lab activities:
 Exercises – Solubility
classification and
chemical tests
 Solubility Test
Classification
 Common Chemical tests
PowerPoint
ACD Chemsketch software
Laptop – each group must
bring one
Handout: Organic
Nomenclature, Physical
and Chemical Properties
Short Quizzes
PowerPoint
Handout-Organic Qualitative
Analysis with problem sets
Short Quizzes
1st Long Exam
Content
MASS SPECTROMETRY
I. Introduction
II. Instrumentation
III. The Molecular Ion
IV. The Ionization Process
V. The Nitrogen Rule
VI. Molecular Formula
Determination
VII. Accurate Mass
VIII. Isotope Ratio Data
A. Common Elements in
Organic Compounds
B. Bromine and Chlorine
IX. Fragmentation Patterns for
Organic Functional Groups
INFRARED SPECTROSCOPY
I. Background Information
A. Electromagnetic Radiation
B. Molecular Vibrations
C. Infrared Spectroscopy
Basics
II. Instrumentation
III. General Approach to IR
Spectrum Analysis
IV. Table of Functional Group
Absorptions
V. Example Spectra for Various
Functional Groups
ULTRAVIOLET/VISIBLE
SPECTROSCOPY
I. Background Information
A. Basics of Ultraviolet Light
Absorption
Specific Objectives
Schedule/
hrs
The student should be able to:
1. Analyze free-radical halogenations at the
mechanistic level;
2. Recognize the different types of hydrogen
and carbon atoms;
3. Predict the halogenations products of
alkanes and cycloalkanes
4. Suggest some methods of preparation of
alkenes and alkynes;
5. Predict the product formed from the
different oxidation reactions of alkenes
and alkynes;
6. Propose structures for alkenes and alkynes
from their oxidative cleavage products;
9 (lec)
12 (lab)
The student should be able to:
1. Predict the products formed by benzene
and its derivatives in substitution
reactions;
2. Write mechanisms for EAS and NAS
reactions of benzene and its derivatives;
3. Predict the oxidation products of
alkylbenzenes; and
4. Suggest synthetic routes for preparing
simple aromatic compounds.
4.5 (lec)
6 (lab)
The student should be able to:
1. Predict the products of the following
reactions of alcohols and alkyl halides:
4.5 (lec)
6 (lab)
Activities/Methodologies/
Teaching Strategies
Lecture
Board Work
Problem Sets
Group homework/project
Materials
Evaluation/
Assessment
Technique
PowerPoint
Handout: Mass Spectrometry
including problem sets
Short Quizzes
Powerpoint
Handout: IR Spectroscopy
with example spectra and
problem sets
Short Quizzes
2nd Long Exam
Powerpoint
Handout: UV/Vis
Spectroscopy; Table of
Short Quizzes
Lab activities:
 Group Work – identify
organic compounds
based on the given
property and mass
spectra
Lecture
Board Work
Problem Sets
Lab activities:
 Group Work – identify
organic compounds
based on the given
property and infrared
spectra
Lecture
Board Work
Problem Sets
Content
B. Measurement and
Presentation of the
Spectrum
C. UV/Vis Spectroscopy
Generalizations
II. Types of Electronic
Transitions
III. Empirical Rules for
Caluclating Uv/Vis
Absorptions
A. Woodward-Fieser Rules
for Dienes
B. Woodward's Rules for
Conjugated Carbonyl
Compounds
C. Mono-Substituted
Benzene Derivatives
D. Di-Substituted Benzene
Derivatives
E. Benzoyl Derivatives
NMR BASICS and 1H RESONANCE
I. Nuclear Spin States
II. Chemical Shift
III. Instrumentation
IV. Solvents for 1H NMR
V. Information Obtained From
NMR Spectroscopy
A. Chemical Equivalence
B. Integration
C. Factors Influencing
Chemical Shift
D. 1H Correlation Chart
E. Spin-Spin Splitting (n + 1
Specific Objectives
2.
Schedule/
hrs
reaction as acids and bases, elimination of
water (dehydration) or HX, and
nucleophilic substitution; and
Determine the necessary reagents and
reaction conditions that bring about the
reactions of alcohols and alkyl halides
The student should be able to:
1. Suggest some methods for the laboratory
preparation of aldehydes and ketones;
2. Predict the products formed in the
reactions of aldehydes and ketones; and
3. Determine the necessary
reagents/reaction conditions that bring
about certain transformations of
aldehydes and ketones to other
compounds.
Activities/Methodologies/
Teaching Strategies
Lab activities:
 Group Work calculating UV/Vis
Adsorption
4.5 (lec)
6 (lab)
Lecture
Board Work
Problem Sets
Lab activities:
 Group Work – identify
organic compounds
based on the given
spectra
Materials
Evaluation/
Assessment
Technique
empirical rules for
calculating UV/Vis
Adsorption
Powerpoint
Handout: 1H NMR
Short Quizzes
Content
Specific Objectives
C RESONANCE
I. Background
II. 13C Correlation Chart
III. 13C NMR Spectroscopy
A. Proton-Coupled 13C
Spectra
B. Proton-Decoupled 13C
Spectra
C. Off-Resonance ProtonDecoupled 13C Spectra
IV. Special Considerations in 13C
NMR Spectroscopy
A. Nuclear Overhauser
Enhancement
B. Problems With
Integration of 13C Spectra
C. Heteronuclear Coupling in
13
C Spectra
The student should be able to:
1. Recognize the sources and use of
carboxylic acids and their functional
derivatives.
2. Correlate the chemical properties of
carboxylic acids and their derivatives with
their molecular structures;
3. Predict the products in the
interconversion reactions of carboxylic
acids and derivatives;
4. Determine the possible route for
interconversion of carboxylic acids and
derivatives; and
5. Suggest some simple methods for the
preparing carboxylic acids and their
derivatives.
Schedule/
hrs
Activities/Methodologies/
Teaching Strategies
Materials
Evaluation/
Assessment
Technique
Rule)
13
I. Determination of molecular
structure from combined
chemical and spectroscopic data
The student should be able to:
1. Determine the structure of the organic
compound using the given information
from different combinations of
spectroscopic data.
4.5 (lec)
6 (lab)
Lecture
Board Work
Problem Sets
Powerpoint
Handout: 13C NMR
Short Quizzes
Problem Sets
3rd Long Exam
(lecture)
Powerpoint
Problem Sets
Problem Sets
3rd Long Exam
(laboratory –
take home)
Lab activities:
 Group Work – identify
organic compounds
based on the given
spectra
6-12 (lab)
Lecture
Board Work
Problem Sets
Lab activities:
 Group Work – identify
organic compounds
based on the given
properties and spectra
VIII. COURSE REQUIREMENTS
Midterm and Final Exam, Short and Long Quizzes, Assignment/Seatworks/Group Homework, Lab Report and Problem Sets.
IX. GRADING SCHEME
LECTURE
Assignment/Seatwork
Short Quiz
Long Exam (3)*
Total
LABORATORY
Lab Work Reports/Problem Sets
Assignment/Seatwork
Long Exam (3)*
Total
10%
15%
75%
100%
45%
10%
45%
100%
*Long Exams for laboratory and lecture are separate.
X. REFERENCES
*all handouts and links for other references and useful software are available at buchem.weebly.com (regularly updated)
Prepared By:
Recommending Approval:
Approval:
MICHAEL V. MONTEALEGRE
Instructor
SAMUEL C. BOBILES
Chairman, Department of Chemistry
AMELIA A. DOROSAN, Ph.D.
Dean, BU College of Science