Download Fundamentals of Organic Chemistry

Metropolitan Community College
COURSE OUTLINE FORM
(Page 1 of 6)
Course Title:
Fundamentals of Organic Chemistry
Course Prefix & No.:
LEC:
LAB:
CHEM 2310
5.0
0.0
Credit Hours:
6.0
COURSE DESCRIPTION: CHEM 2310 provides the student with an overview of the importance of organic
molecules and their reactions. Topics include bonding, 3-D structure, and the relationship between structure, and
reaction mechanisms as applied to hydrocarbons, alcohols, aldehydes, ketones, carboxylic acids and amines and their
derivatives. The relationship of these compounds to biochemical is also discussed. Students registering for this course
must also register for CHEM 2310L which is the laboratory component of the course.
COURSE PREREQUISITE (S): College-level reading, writing, and math proficiency and CHEM 1010 (or an equivalent
course) with a grade of C or better within the past four years
COURSE CO-REQUISITE: CHEM 2310L
RATIONALE: The purpose of this course is to provide the student with the basic information necessary to understand
carbon chemistry. This provides the foundation for further studies in the chemistry of biological systems.
REQUIRED TEXTBOOK (S) and/or MATERIALS:
Title:
Introduction to Organic Chemistry
Edition:
2014/05
Author:
Brown & Poon
Publisher:
Wiley & Sons
Materials:
Safety Googles
Attached course outline written by: Bernadette Corbett
Date: Fall, 2001
Bernadette Corbett
Date: Fall, 2014
Reviewed/Revised by:
Effective quarter of course outline: 15/FA
Academic Dean:
_________Date:______
_ Date:
Course Objectives, Topical Unit Outlines, and Unit Objectives must be attached to this form.
ESO Revised 3-13-01
Metropolitan Community College
COURSE OUTLINE FORM
(Page 2 of 6)
TITLE: Fundamentals of Organic Chemistry
PREFIX/NO: CHEM 2310
COURSE OBJECTIVES:
Upon completion of CHEM 2310, the student will be able to:
1. understand and explain the important role carbon compounds play in life systems;
2. explain the role of carbon compounds in our economy and in our dally life;
3. describe covalent bonding as it applies to organic compounds and then relate this bonding to the structure of organic
compounds and how it influences their properties;
4. demonstrate an understanding of acid-base chemistry and how it relates to organic chemistry;
5. describe the difference between constitutional isomerism and stereoisomerism and how they relate to the properties of
organic compounds;
6. describe and identify the various classifications of organic compounds based on functional groups, including structure and
nomenclature;
7. demonstrate an understanding of how a reaction occurs based on the mechanism of the individual types of reaction;
8. apply the above principles to one or more of the principle classes of biochemical molecules (for example, carbohydrates,
lipids, proteins, etc.);
TOPICAL UNIT OUTLINE/UNIT OBJECTIVES:
Unit I
Organic Bonding and Isomerism
On completion of this unit, the student will be able to:
1. describe covalent bonding as it relates to organic chemistry including:
a. hybrid orbitals
b. sigma and pi bonds
c. polar and nonpolar bonds
d. molecular shapes and molecular polarity
2. distinguish between a molecular and structural formula and draw valid structural formulas from molecular formulas;
3. distinguish between different types of isomers including constitutional and stereoisomers;
4. determine the formal charge on organic compounds;
5. demonstrate an understanding of resonance and an ability to draw resonance hybrids of organic compounds;
6. classify the major organic compounds by functional group.
Unit II
Acids and Bases as Applied to Organic Chemistry
On completion of this unit, the student will be able to:
1. Identify acids and based according to Arrhenius, Bronsted-Lowry and Lewis and distinguish between the three
definitions.
2. Describe weak acids and bases according to the Bronsted-Lowry definition and explain their strength in terms of
equilibrium reactions.
3. Explain how acids and bases are used in organic chemistry
ESO Revised 3-13-01
Metropolitan Community College
COURSE OUTLINE FORM
(Page 3 of 6)
Unit III Hydrocarbons
On completion of this unit, the student will be able to:
1.
2.
3.
4.
5.
6.
distinguish between an alkane, alkene, alkyne and an aromatic by structure.
name each type of hydrocarbon by means of the IUPAC system.
describe the physical properties of hydrocarbons and how these relate to biochemical properties.
Use alkanes as model compounds to describe
a. Constitutional isomers
b. Conformational isomers
c. Stereoisomers (cis/trans) as applied to cyclic alkanes
d. An introduction to chemical reactions – combustion and free-radical halogenation
Use alkenes as model compounds to describe
a. Stereoisomers (cis/trans) as applied to double bonds
b. Electrophilic addition reactions.
c. define and describe Markovnikov’s rule.
d. Compare/contrast the reactions of alkenes and alkynes
Use benzene as a model aromatic hydrocarbon to describe
e. describe the structure, resonance model and orbital model form benzene.
f. describe the electrophilic substitution mechanism in aromatic compounds.
g. distinguish between ring-activating and ring-deactivating substituents as well as the different directing groups in
aromatic disubstitution reactions.
Unit IV Stereoisomerism
On completion of this unit, the student will be able to:
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
describe the difference between constitutional isomers and stereoisomers in alkanes
identify chiral molecules
recognize using molecular models the different enantiomers of a compound.
predict from its structure whether a compound can have enantiomers.
describe the physical and chemical properties of enantiomers.
distinguish between enantiomers, diastereomers, and meso compounds.
name configurational isomers by either the R-S or E-Z convention where appropriate.
define a racemic mixture and explain how to resolve it.
relate stereoisomerism to biological compounds.
explain the role of stereoisomers in defining physiological activity.
Unit IV Substitution and Elimination Reactions: Organic Halogen Halides
On completion of this unit, the student will be able to:
1.
2.
3.
4.
5.
6.
define a nucleophile and its role in a chemical reaction;
define a nucleophilic substitution reaction using organic halogen halides as reagents.
give some examples of nucleophilic substitution reactions.
distinguish between an SN1 and SN2 mechanism with respect to nucleophiles, solvents and structure.
predict whether a given reaction goes by either an SN1 or SN2 mechanism.
distinguish between and E1 or E2 reaction mechanism.
ESO Revised 3-13-01
Metropolitan Community College
COURSE OUTLINE FORM
(Page 4 of 6)
Unit V
Alcohols, Ethers, Thiols and Phenols
On completion of this unit, the student will be able to:
1.
2.
3.
4.
5.
6.
7.
8.
9.
Name alcohols by the IUPAC system.
Relate the physical properties of alcohols to hydrogen bonding.
Describe acidity and basicity as it relates to alcohols and phenols by using the Bronsted-Lowery definition and pKa
values.
Explain the relative acidity of alcohols by means of either the resonance or inductive effect.
Predict the products of alcohols in the following reactions: dehydrations and oxidations.
Compare alcohols to thiols in terms of reactivity
Describe the physiological significance of thiols
Identify ethers and describe their properties as compared to alcohols
Identify phenols and identify their properties, particularly acidity, as compared to alcohols
Unit VI Aldehydes and Ketones
On completion of this unit, the student will be able to:
1.
2.
3.
4.
5.
6.
7.
8.
Unit VII
distinguish between and aldehyde and ketone.
name aldehydes and ketones both by common names and the IUPAC system.
describe the characteristics of the carbonyl group and how these characteristics allow for nucleophilic addition
reactions.
predict the products of the nucleophilic addition reactions in aldehydes and ketones particularly the addition of water
to form hydrates and alcohols to form hemiacetals and acetals;
describe Keto-Enol tautomerism in aldehydes and ketones.
describe the formation of the enolate anion using the acidic properties of -hydrogens.
predict the products of aldol condensation reactions.
relate the structure and properties of alcohols, aldehydes and ketones to carbohydrates.
Carboxylic Acids and Carboxylic Acid Derivatives
On completion of this unit, the student will be able to:
1.
2.
3.
4.
5.
6.
7.
recognize and name carboxylic acids both by common and IUPAC names.
describe the physical properties of carboxylic acids, especially with respect to their intermolecular interactions.
describe the acidity or carboxylic acids with particular emphasis as compared to mineral acids.
describe resonance and inductive effects as they relate to the acidity of carboxylic acids.
describe the formation of carboxylic acids by oxidation of alcohols.
describe the formation of the derivatives of carboxylic acids and the relativity reactivity of these derivatives. In
particular:
a. the reaction of acids with thionyl chloride to form acid chlorides
b. the reaction of acids with acid chlorides to form anhydrides
c. the reaction of acids with alcohols to form esters (Fischer esterification).
d. The base promoted hydrolysis of fatty acid esters to form soap (saponification)
relate the structure and properties of carboxylic acids and esters to lipids.
ESO Revised 3-13-01
Metropolitan Community College
COURSE OUTLINE FORM
(Page 5 of 6)
Unit VIII Amines and Related Nitrogen Compounds
On completion of this unit, the student will be able to:
1.
2.
3.
4.
5.
6.
Classify amines according to structure
provide accurate names for amines
describe the physical properties for amines with particular emphasis on intermolecular interactions.
describe the basicity of amines with particular emphasis on a comparison with inorganic bases
describe the reactions of amines as nucleophiles.
Describe the reaction of amines with carboxylic acids to form amides, particular in relation to the formation of
peptide bonds/
COURSE REQUIREMENTS/EVALUATION:
A minimum of four tests will be administered over the course of the course. Each test will be worth 100 points. Along
with the grade points accumulated for the tests, homework assignments and quizzes may be assigned at the discretion of
the instructor. Each student will also complete a comprehensive final exam that is created to correlate with the exams
used by the American Chemical Society to assess student mastery of organic chemistry. The final Grade for the course
will be computed as:
Test/Quiz grades = 50%
Homework = 10%
Lab grade = 20%
Final exam = 20%
COURSE OBJECTIVES/ASSESSMENT MEASURES
COURSE OBJECTIVES
1. understand and explain the important role
compounds play in life systems;
ASSESSMENT MEASURES
carbon
Participate in discussions and be able to provide
specific examples of carbon compounds that play
a role in physiology
2. explain the role of carbon compounds in our economy and
in our dally life;
Participate in discussion and be able to provide and/or
recognize specific examples of carbon compounds
that are used in everyday life and explain their
value to our economy or to our daily life.
3. Describe covalent bonding as it applies to organic
compounds and then relate this bonding to the structure
of organic compounds
classroom testing and homework assignments will
assess basic knowledge;
A minimum average score of 70% is required for each
type of assignment.
ESO Revised 3-13-01
Metropolitan Community College
COURSE OUTLINE FORM
(Page 6 of 6)
4. demonstrate an understanding of acid-base chemistry and
how it relates to organic chemistry
classroom testing and homework assignments will
assess basic knowledge;
A minimum average score of 70% is required for each
type of assignment.
5. describe the difference between constitutional isomerism
and stereoisomerism and how they relate to the
properties of organic compounds
classroom testing and homework assignments will
assess basic knowledge;
A minimum average score of 70% is required for each
type of assignment.
6. describe and identify the various classifications of organic
compounds based on functional groups, including
structure, nomenclature and reaction chemistry
classroom testing and homework assignments will
assess basic knowledge;
A minimum average score of 70% is required for each
type of assignment.
7. demonstrate an understanding of how a reaction occurs
based on the mechanism of the individual types of
reaction
classroom testing and homework assignments will
assess basic knowledge;
A minimum average score of 70% is required for each
type of assignment.
8. Apply the above principles to one or more of the principle
biochemical molecules (for example, carbohydrates,
lipids, proteins, etc.)
classroom testing and homework assignments will
assess basic knowledge;
A minimum average score of 70% is required for each
type of assignment.
ESO Revised 3-13-01