CHEM 2323 – Organic Chemistry II
Course Description:
Continuation of CHEM 2223 utilizing mechanistic interpretations of reaction of aliphatic and aromatic hydrocarbons,
alcohols, ethers, aldehydes, ketones, acids and amines.
Prerequisites:
CHEM 2223
Required Text:
Organic Chemistry (2 nd Edition), Janice Gorzynski Smith, McGraw Hill 2008
Instructional Objectives:
It is the objective of this class that students acquire understanding of these parts of Organic Chemistry:
1.
The chemistry and wide reactivity of alcohols, ethers, and epoxide compounds.
2.
The important oxidation and reduction reactions of organic compounds.
3.
The electronics and reactivities of conjugated diene compounds.
4.
The structures, stabilities, redox properties, and reactivities of aromatic compounds.
5.
The chemistries of carbonyl compounds, amine compounds, and carboxylic acid derivatives, particularly the
expression of these chemistries in amino acids, proteins, and carbohydrates.
Instructional Objectives of the Laboratory Component:
The lab part of Organic II is the preparation and identification of organic compounds by small teams of students. Methods
of preparation will be developed and reviewed by students in consultation with professors. Students will collect data on
intermediate and product compounds with laboratory instrumentation. Students will develop experience in data
acquisition and interpretation of spectra, including those of mass spectrometry, FTIR, and NMR.
Assessment:
Evaluation Methods and Criteria:
Students’ progress will be evaluated through homework assignments, exams, laboratory exercises, and laboratory reports.
The final grade will be based on a weighted average of the grades attained on exams, homework, and laboratory performance.
The distribution is as follows:
Three exams
45%
Homework
10%
Final exam
20%
Laboratory
25%
Course Outline:
Week 1: General Introduction to CHEM 2323; review quiz; nucleophilic substitution reactions; SN1, SN2, E1 and E2
reactions and their mechanisms.
Week 2: Alcohols, ethers, epoxides: general features; preparation and reactions of alcohols.
Week 3: Alkenes: unsaturation; preparations; addition reactions; Markovnikov’ s rule; stereochemistry of HX addition;
halogenations; hydroboration-oxidation.
Week 4: Alkynes: preparation of alkynes; addition of HX; hydration; hydroboration reactions; reactions of acetylides.
Week 5: Review and Exam 1
Week 6: Review of alcohols, preparation and reactions; introduction to oxidation and reduction: organic chemistry
definitions.
Week 7: Organic oxidation and reduction, continued: oxidizing agents; hydroxylation oxidative cleavage reactions;
stereospecific epoxidation reactions.
Week 8: Mass spectrometry; infrared spectrometry; NMR spectroscopy: descriptions of the technologies and interpretation
of spectra.
Week 9: Review and Exam 2.
Week 10: Radical reactions: general features; halogenation of alkanes.
Week 11: Conjugation, resonance, and dienes: the effects of electronic structure on chemical reactivity; kinetic and
thermodynamic products; Diels-Alder reaction.
Week 12: Benzene and aromatic compounds: aromaticity; Huckel’ s rule; electrophilic aromatic substitution:
halogenations, nitration; sulfonation.
Week 13: Review and Exam 3.
Week 14: Carboxylic acids and the acidity of the O-H bond; carbonyl chemistry: oxidations and reductions of carbonyls;
organometallic reagents.
Week 15: Aldehydes and Ketones – nucleophilic addition reactions.
Week 16: Student presentations of subjects in biochemistry; review and final exam.
CHEM 2323L LAB ORATORY SYLLAB US: INDEPENDENT TEAM RESEARCH PROJECTS
SYLLABUS
LAB
SUBJECT
Wilcox TEXT
1
Check in; safety; notebooks
Ch 1, 2; front cover
2
3
4
5
6
7
Conversion of alcohols to alkyl halides
Grignard prep’ n of 2-methylhexenes
Grignard prep’ n of 2-methylhexenes
IR spectroscopy of Grignard products
NMR spectroscopy
Cyclohexanone from cyclohexanol; NMR of ketone products
vs alcohol reactant
Introduction and general description of solar energy
conversion, with emphasis of opportunities and challenges.
Assignment: research and prepare summary of solar energy
conversion, bio-mimetic preparation of fuels, description of
photosynthetic reaction centers in plants.
Library research: understanding information-finding tools
available in the library and on-line; understanding how to
search chemistry literature and databases of chemical
information. P resentations by library information specialist.
Ch 18; (A)
Ch 22; (A), (B), (C), (D)
continued
Ch 13
8
9
10
11
12
13
Assignment: literature search of (1) coupling reactions, and
(2) methods of preparing free base-tetraphenylporphyrin
(H 2TP P ).
P reparation and characterization of H 2TP P product.
Group meeting: P resentations by 2- or 3- person teams on
coupling reactions and porphyrin preparation.
Literature search followed by in-lab: nitration and reduction
of H 2TP P to form mono-amino tetraphenylporphyrin, H 2TP P NH 2; preparation and analysis.
Ch 25; (B), (C)