HIBBING COMMUNITY COLLEGE
COURSE OUTLINE
COURSE TITLE & NUMBER: Organic Chemistry 2: CHEM 2720
CREDITS: 5 (4 Lec/1 Lab)
PREREQUISITES: CHEM 2710: Organic Chemistry 1
CATALOG DESCRIPTION:
Organic Chemistry 2: CHEM 2720 is a continuation of Organic Chemistry 1. The
chemistry of carbon compounds emphasizing the theories and mechanisms which
account for their physical and chemical properties is again studied. Techniques of
purification, separation, and synthesis are practiced in the laboratory. Organic
Chemistry 2 is meant for students planning to major in biology, chemistry, chemical
engineering, pharmacy, and certain medical fields.
OUTLINE OF MAJOR CONTENT AREAS:
I.
II.
III.
IV.
Conjugated unsaturated systems
A.
Allyic substitution and the allyl radical
B.
Alkadienes and polyunsaturated hydrocarbons
C.
The stability of conjugated dienes
D.
The Diels-Alder reaction
Spectroscopic methods
A.
IR spectra
B.
NMR spectra
Aromatic compounds
A.
Structure and properties of benzene
B.
Nomenclature
C.
Huckel's Rule
D.
Other aromatic compounds
E.
Electrophilic aromatic substitution reactions
1.
Halogenation
2.
Nitration
3.
Sulfonation
4.
Friedel-Crafts alkylations
5.
Friedel-Crafts acylation
Aldehydes and ketones
A.
Nomenclature
B.
Physical properties
C.
Synthesis of aldehydes
1.
Oxidation of primary alcohols
CHEM2720
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V.
VI.
2.
Reduction of acyl chlorides, esters, and nitriles
3.
Ozonolysis of alkenes
D.
Synthesis of ketones
1.
Oxidation of secondary alcohols
2.
Friedel-Crafts acylation
3.
Ozonolysis of alkenes
4.
Reaction with lithium dialkylcuprates
E.
Reactions of aldehydes and ketones
1.
Addition of organometallic compounds
2.
Addition of hydride ion
3.
Addition of hydrogen cyanide
4.
Addition of ylides
5.
Addition of alcohols
6.
Addition of derivatives of ammonia
7.
Aldol condensations
Carboxylic acids
A.
Nomenclature
B.
Physical properties
C.
Synthesis
1.
Oxidation of aldehydes and primary alcohols
2.
Oxidation of alkenes
3.
Oxidation of alkylbenzenes
4.
Oxidation of methyl ketones
5.
Carbonation of Grignard reagents
6.
Hydrolysis of nitriles
D.
Reactions
1.
Salt formation
2.
Reduction
3.
Conversion to acyl chlorides
4.
Conversion to acid anhydrides
5.
Conversion to esters
6.
Conversion to lactones
7.
Conversion to amides and imides
8.
Conversion to lactams
9.
α - halogenation
10.
Decarboxylation
E.
Acyl chlorides
F.
Acid anhydrides
Esters
A.
Nomenclature
B.
Physical properties
C.
Synthesis
1.
Esterification
2.
From acid chloride or anhydrides
D.
Reactions
1.
Hydrolysis
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VII.
VIII.
IX.
X.
XI.
2.
Transesterification
3.
Conversion to amides
4.
Reaction with Grignard reagents
5.
Reduction
Amides
A.
Nomenclature
B.
Physical properties
C.
Synthesis
D.
Reactions
1.
Hydrolysis
2.
Conversion to nitriles
3.
Conversion to imides
β - dicarbonyl compounds
Amines
A.
Nomenclature
B.
Physical properties
C.
Synthesis
1.
Gabriel synthesis
2.
By Reduction of alkyl azides
3.
By Amination of alkyl halides
4.
By reduction of nitrorenes
5.
By reductive amination
6.
By reduction of amides, nitriles and ozimes
7.
Through the Hofmann and Curtis rearrangements
D. Reactions
1.
As Bases
2.
Diazotization
3.
Conversion to sulfonamides
4.
Conversion to amides
5.
Hofmann and Cope eliminations
Phenols
A.
Nomenclature
B.
Physical properties
C.
Synthesis
1.
Via arenediazonium salts
2.
Dow process
3.
From sodium benzenesulfonates
4.
Via cumene hydroperoxide
D. Reactions
1.
As acids
2.
Williamson synthesis
3.
Acylation
4.
Electrophilic aromatic substitution
Aryl halides
A.
Nomenclature
B.
Physical properties
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C.
D.
Synthesis
1.
By electrophilic aromatic substitution
2.
Via arenediazonium salts
Reactions
1.
Electrophilic aromatic substitution
2.
Nucleophilc aromatic substitution
COURSE GOALS/OBJECTIVES/OUTCOMES:
The student will
1.
recognize reactions that are enhanced by resonance stabilization of the
intermediates.
2.
predict the products of Diels-Alder reactions.
3.
identify the key features of IR and NMR spectra.
4.
describe the physical properties of aromatic compounds, aldehydes, ketones,
carboxylic acids, esters, amides and amines.
5.
describe synthesis routes for aromatic compounds, aldehydes, ketones,
carboxylic acids, esters, amides, and amines.
6.
describe the chemical reactions of aromatic compounds, aldehydes, ketones,
carboxylic acids, esters, amides, and amines.
7.
use the IUPAC system to name aromatic compounds, aldehydes, ketones,
carboxylic acids, esters, amides, and amines.
8.
obtain IR spectra of laboratory samples.
9.
identify unknown organic compounds in the laboratory using basic chemical
procedures.
HCC COMPETENCIES MET:
Thinking Creatively & Critically
STUDENT ASSESSMENT SHALL TAKE PLACE USING INSTRUMENTS
SELECTED/DEVELOPED BY THE COURSE INSTRUCTOR.
SPECIAL INFORMATION: (SPECIAL FEES, DIRECTIVES ON HAZARDOUS
MATERIALS, ETC.)
Hazardous chemicals will routinely be used in laboratory. Students will be
supplied with pertinent information relating to these materials at the appropriate
time.
AASC APPROVAL DATE: December 19, 2012
REVIEW DATE:
December 2017
CHEM2720:so
121912
CHEM2720
4
Hibbing Community College, a technical & community college, is
an equal opportunity educator & employer