07/29/14
X
DATE
REQUIRED COURSE
ELECTIVE COURSE
DIVISION
NEW COURSE
REVISION
X
LAKE LAND COLLEGE
Course Information Form
COURSE NUMBER
CHM 244
TITLE
SEM CR HRS 4.00
LT HRS
4.00
Organic Chemistry II
LAB HRS
0.00
SOE HRS
ECH
(Assigned by Administration)
COURSE PCS#
Prerequisites: CHM 243
Catalog Description (40 Word Limit): Course is the second semester of a two-semester sequence.
Topics include an intensive look at reaction mechanisms involving carbonyls, aromatics, and other πsystems. To be taken concurrently with CHM 254.
List the Major Course Segments (Units)
Contact Lt Hrs
Organic Synthesis
Aromaticity and π-systems—Orbital Interactions
Nucleophilic Addition to Polar π-Bonds
Nucleophilic Addition-Elimination Reactions
Electrophilic Aromatic Substitution
Diels-Alder Reaction
Free Radical Reactions
EVALUATION:
Textbook:
Quizzes
Lab Work
x
Exams
Projects
9
5
12
12
12
5
5
x
Oral Pres.
Comp Final
x
Title: Organic Chemistry: Principles and Mechanisms
Author: Joel Karty
Publisher: Norton
Volume/Edition:
1st
Copyright Date:
2014
Contact Lab Hrs
Papers
Other
Major Course Segment
Hours
Learning Outcomes
Student will be able to:
Organic Synthesis
Beginning concepts
Intermediate topics
9
Apply organic reactions and concepts toward the synthesis of
compounds. Learn the art of retrosynthesis and the use of
protecting groups to avoid synthetic traps. Manipulate
functional groups through the use of oxidation and reduction
sequences.
Aromaticity and π-Systems
5
Learn how use multiple center MO’s to predict and recognize
aromatic character in cyclic compounds. Apply aromatic
concepts to the structure of DNA.
Nucleophilic Addition to Polar πBonds
Addition of strong Nucleophiles
Addition of Weak Nucleophiles
12
Master the various types of carbonyl reactions that follow the
nucleophilic addition mechanistic pathway. These include
hydride reductions, organometallic additions, Wittig reactions,
conjugate addition reactions. Also investigated will be the
formation and hydrolysis of acetals, imines, enamines, and
nitriles, the Wollf-Kishner reductions, aldol addtions, aldol
condensations, and the Robinson annulation. Apply these
concepts to the ring opening and closing of
monosaccaharides.
Nucleophilic Addition-Elimination
Reactions
Strong Nucleophiles
Weak Nucleophiles
12
Develop an understanding of carbonyl reactions that proceed
through the nucleophilic addition-elimination pathway.
Reactions include ester saponification, acyl substitution of acid
derivatives, hydrolysis of acid derivatives, Gabriel synthesis,
haloform reactions, hydride reductions, organometallic
reactions, aminolysis of acid derivatives, synthesis of acid
halides, HVZ reaction, Baeyer-Villiger oxidations, Claisen
Condensations, maloinc ester syntheses, and acetoacetic
ester syntheses. Apply these concepts to amino acid
sequencing and the synthesis of peptides.
Electrophilic Aromatic Substitution
12
Understand basics of SEAr on unsubstituted benzene rings.
These reactions will then be tied into larger synthetic schemes
The application of these reactions to mono- and disubstituted
benzenes will also be developed. Students will also learn
about the SNAr pathways and how they differ from the SEAr
pathway..
Diels-Alder (Pericyclic) Reactions
5
Understand mechanism of the Diels-Alder and other simple
pericyclic reactions. Students should be able to predict
stereochemistry and regionchemistry of the adducts formed.
The use of these reactions in synthesis will also be covered.
Free Radical Reactions
5
Gain and understanding of radical based reaction
mechanisms, with a specific focus on halogenation of alkanes,
free radical addition of HBr, and dissolving metal reductions.
Course Outcomes: At the successful completion of this course, students will be able to:

Continue to develop a mechanistic understanding of Organic Chemistry.

Develop an understanding of π-systems and what it means to be aromatic.

Gain an extensive knowledge of π-system reactions, including carbonyl, aromatic, and
conjugated system chemistry.

Learn how radicals can be involved in chemical processes and how they participate from a
mechanistic viewpoint.

Continue to apply concepts to the understanding of biomolecule structure and function.

Learn to connect concepts in a logical manner through the use and application of organic
synthesis.