Download EASTERN ARIZONA COLLEGE General Organic Chemistry I

EASTERN ARIZONA COLLEGE
General Organic Chemistry I
Course Design
2015-2016
Course Information
Division
Science
Course Number
CHM 235 (SUN# CHM 2235)
Title
General Organic Chemistry I
Credits
4
Developed by
Phil McBride
Lecture/Lab Ratio
3 Lecture/3 Lab
Transfer Status
ASU
NAU
CHM 233 (3) & CHM CHM 235L --and-237 (1)
CHM 235
Activity Course
No
CIP Code
40.0500
Assessment Mode
Pre/Post Test (62 Questions/130 Points)
Semester Taught
Fall
GE Category
Lab Science
Separate Lab
Yes
Awareness Course
No
Intensive Writing Course
No
UA
CHEM 243A --and-CHEM 241A
Prerequisites
CHM 152
Educational Value
Students will gain an understanding of the role that organic chemistry plays in their lives, and the role that
organic chemistry plays in the agricultural and medical fields. Students learn how to identify problems and
work as a team to solve those problems. Students learn how to predict reactions and devise methods to
synthesize organic compounds. Students learn to work as part of a cooperative team.
Students learn the composition and reactivity of several chemicals that they will encounter in various
scientific fields. The students learn about hazardous waste and safety precautions that must be followed
when dealing with organic chemicals.
Description
General principles of organic chemistry with emphasis on reactivity and synthesis. Topics include
bonding, structure and properties of organic compounds, stereochemistry, overview of organic reactions,
kinetics and thermodynamics, structure, synthesis, and reaction of alkenes, alkynes, and alkyl halides,
nucleophilic substitution and elimination reactions, structure determination using Mass Spectrometry,
Infrared Spectroscopy, and Nuclear Magnetic Resonance Spectroscopy, aromaticity, and electrophilic
aromatic substitution reactions.
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General Organic Chemistry I
Supplies
Laboratory Notebook: Comp Book 5x5 Ruled
Scientific Calculator
Competencies and Performance Standards
1.
Review the principles of atomic and molecular structure, bonding, and acid-base
chemistry.
Learning objectives
What you will learn as you master the competency:
a.
Draw and interpret Lewis, condensed, and line-angle structural formulas. Show which
atoms bear formal charges.
b.
Draw resonance forms and use them to predict stabilities.
c.
Calculate empirical and molecular formulas from elemental compositions.
d.
Predict relative acidities and basicities based on structure, bonding, and resonance of
conjugate acid-base pairs.
e.
Identify nucleophiles (Lewis bases) and electrophiles (Lewis acids), and write equations
for Lewis acid-base reactions.
Performance Standards
Competence will be demonstrated:
o
through completion of a weekly laboratory report.
o
through successful completion of periodic written examinations.
Criteria - Performance will be satisfactory when:
2.
o
learner completes assigned homework.
o
learner participates in class activities.
o
learner completes stipulated laboratory activities.
Visualize the structure and properties of Organic Molecules.
Learning objectives
What you will learn as you master the competency:
a.
Draw the structure of a single bond, a double bond, and a triple bond.
b.
Predict the hybridization and geometry of the atoms in a molecule.
c.
Draw a good three-dimensional representation of a given molecule.
d.
Identify constitutional isomers and stereoisomers.
e.
Identify polar and nonpolar molecules and predict which ones can engage in hydrogen
bonding.
f.
Predict general trends in the boiling points and solubilities of compounds, based on their
size, polarity, and hydrogen-bonding ability.
g.
Identify the general classes of hydrocarbons and draw structural formulas for examples.
h.
Identify the classes of compounds containing oxygen or nitrogen, and draw structural
formulas for examples.
Performance Standards
Competence will be demonstrated:
o
through completion of a weekly laboratory report.
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General Organic Chemistry I
o
through successful completion of periodic written examinations.
Criteria - Performance will be satisfactory when:
3.
o
learner completes assigned homework.
o
learner participates in class activities.
o
learner completes stipulated laboratory activities.
Acquaint self with the structure and stereochemistry of Alkanes.
Learning objectives
What you will learn as you master the competency:
a.
Explain and predict trends in physical properties of alkanes.
b.
Correctly name alkanes, cycloalkanes, and bicyclic alkanes.
c.
Draw the structure and give the molecular formula, when given the name of an alkane.
d.
Compare the energies of alkane conformations and predict the most stable
conformation.
e.
Compare the energies of cycloalkanes and explain ring strain.
f.
Identify and draw cis and trans stereoisomers of cycloalkanes.
g.
Draw accurate cyclohexane conformations, and predict the most stable conformations of
substituted cyclohexanes.
Performance Standards
Competence will be demonstrated:
o
through completion of a weekly laboratory report.
o
through successful completion of periodic written examinations.
Criteria - Performance will be satisfactory when:
4.
o
learner completes assigned homework.
o
learner participates in class activities.
o
learner completes stipulated laboratory activities.
Develop an understanding of the kinetics and thermodynamics involved in chemical
reactions.
Learning objectives
What you will learn as you master the competency:
a.
Explain the mechanism and energetics of the free-radical halogenation of alkanes.
b.
Predict the products of halogenation of an alkane, based on the selectivity of
halogenation.
c.
Calculate free-energy changes from equilibrium constants.
d.
Calculate enthalpy changes from bond-dissociation energies.
e.
Determine the order of a reaction, and suggest a possible mechanism based on its rate
equation.
f.
Use energy diagrams to discuss transition states, activation energies, intermediates, and
the rate-determining step of a reaction.
g.
Explain how to use isotope effects to determine whether a C-H bond is being broken in
the rate-determining step of a reaction.
h.
Use the Hammond postulate to predict whether a transition state will be reactant-like or
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General Organic Chemistry I
product-like.
i.
Describe the structures of carbocations, carbanions, free radicals, and carbenes and the
structural features that stabilize them. Explain which are electrophilic and which are
nucleophilic.
Performance Standards
Competence will be demonstrated:
o
through completion of a weekly laboratory report.
o
through successful completion of periodic written examinations.
Criteria - Performance will be satisfactory when:
5.
o
learner completes assigned homework.
o
learner participates in class activities.
o
learner completes stipulated laboratory activities.
Visualize the three-dimensional structure of molecules in order to discriminate between
molecules with subtle stereochemical differences.
Learning objectives
What you will learn as you master the competency:
a.
Classify molecules as chiral or achiral, and identify mirror planes of symmetry.
b.
Identify chiral carbon atoms and name them using the (R) and (S) nomenclature.
c.
Calculate specific rotations from polarimetry data.
d.
Draw all stereoisomers of a given structure.
e.
Identify enantiomers, diastereomers, and meso compounds.
f.
Draw correct Fischer projections of chiral carbon atoms.
g.
Predict the stereochemistry of products of reactions such as substitutions and
eliminations on optically active compounds.
h.
Predict the differences in products of stereospecific reactions of diastereomers.
Performance Standards
Competence will be demonstrated:
o
through completion of a weekly laboratory report.
o
through successful completion of periodic written examinations.
Criteria - Performance will be satisfactory when:
6.
o
learner completes assigned homework.
o
learner participates in class activities.
o
learner completes stipulated laboratory activities.
Develop an understanding of the physical properties and reactions of alkyl halides.
Learning objectives
What you will learn as you master the competency:
a.
Predict and explain the rearrangement of cations in first-order reactions.
b.
Predict which substitutions or eliminations will be faster, based on differences in
substrate, base/nucleophile, leaving group, or solvent.
c.
Predict whether a reaction will be first order or second order.
d.
Predict predominance of substitution or elimination, when possible.
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e.
Use the Saytzeff rule to predict major and minor elimination products.
f.
Use retrosynthetic analysis to solve multistep synthesis problems with alkyl halides as
reagents, intermediates, or products.
Performance Standards
Competence will be demonstrated:
o
through completion of a weekly laboratory report.
o
through successful completion of periodic written examinations.
Criteria - Performance will be satisfactory when:
7.
o
learner completes assigned homework.
o
learner participates in class activities.
o
learner completes stipulated laboratory activities.
Construct an understanding of the physical properties and synthesis of alkenes.
Learning objectives
What you will learn as you master the competency:
a.
Draw and name all alkenes with a given molecular formula.
b.
Use the E-Z and cis-trans systems to name geometric isomers.
c.
Use heats of hydrogenation to compare stabilities of alkenes.
d.
Predict relative stabilities of alkenes and cycloalkenes, based on structure and
stereochemistry.
e.
Predict the products of dehydrohalogenation of alkyl halides, dehalogenation of
dibromides, and dehydration of alcohols, including major and minor products.
f.
Propose logical mechanisms for dehydrohalogenation, dehalogenation, and dehydration
reactions.
g.
Predict and explain the stereochemistry of E2 eliminations to form alkenes.
h.
Propose effective single-step and multistep syntheses of alkenes.
Performance Standards
Competence will be demonstrated:
o
through completion of a weekly laboratory report.
o
through successful completion of periodic written examinations.
Criteria - Performance will be satisfactory when:
8.
o
learner completes assigned homework.
o
learner participates in class activities.
o
learner completes stipulated laboratory activities.
Develop an understanding of the reactions of alkenes.
Learning objectives
What you will learn as you master the competency:
a.
Predict the products of additions, oxidations, reductions, and cleavages of alkenes,
including (a) Orientation of reaction (regiochemistry) (b) Stereochemistry.
b.
Propose logical mechanisms to explain the observed products of alkene reactions,
including regiochemistry and stereochemistry.
c.
Use alkenes as starting materials and intermediates in devising one-step and multistep
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syntheses.
d.
Choose the better method and explain its advantages when more than one method is
usable for a chemical transformation.
e.
Use clues provided by products of reactions such as ozonolysis to determine the
structure of an unknown alkene.
Performance Standards
Competence will be demonstrated:
o
through completion of a weekly laboratory report.
o
through successful completion of periodic written examinations.
Criteria - Performance will be satisfactory when:
9.
o
learner completes assigned homework.
o
learner participates in class activities.
o
learner completes stipulated laboratory activities.
Develop an understanding of the physical properties, synthesis, and reactions of alkynes
Learning objectives
What you will learn as you master the competency:
a.
Name alkynes and draw the structure from their names.
b.
Explain why alkynes are more acidic than alkanes and alkenes. Show how to generate
nucleophilic acetylide ions and heavy-metal acetylides.
c.
Propose effective single-step and multistep syntheses of alkynes.
d.
Predict the products of additions, oxidations, reductions, and cleavages of alkynes,
including orientation of reaction (regiochemistry) and stereochemistry.
e.
Use alkynes as starting materials and intermediates in one-step and multistep
syntheses.
f.
Show how the reduction of an alkyne leads to an alkene or alkene derivative with the
desired stereochemistry.
Performance Standards
Competence will be demonstrated:
o
through completion of a weekly laboratory report.
o
through successful completion of periodic written examinations.
Criteria - Performance will be satisfactory when:
10.
o
learner completes assigned homework.
o
learner participates in class activities.
o
learner completes stipulated laboratory activities.
Determine the structure of organic compounds with the use of Infrared (IR) Spectroscopy
and Mass Spectrometry (MS).
Learning objectives
What you will learn as you master the competency:
a.
Given an IR spectrum, identify the reliable characteristic peaks.
b.
Explain why some characteristic peaks are usually strong or weak and why some may
be absent.
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General Organic Chemistry I
c.
Predict the stretching frequencies of common functional groups.
d.
Identify functional groups from IR spectra.
e.
Identify conjugated and strained C=O bonds and conjugated and aromatic C=C bonds
from their absorptions in the IR spectrum.
f.
Determine molecular weights from mass spectra.
g.
Use mass spectra to recognize the presence of Br, C1, I, N, and S atoms, when
possible.
h.
Predict the major ions from fragmentation of alkanes, alkenes, and alcohols.
i.
Use the fragmentation pattern to determine whether a proposed structure is consistent
with the mass spectrum.
Performance Standards
Competence will be demonstrated:
o
through completion of a weekly laboratory report.
o
through successful completion of periodic written examinations.
Criteria - Performance will be satisfactory when:
11.
o
learner completes assigned homework.
o
learner participates in class activities.
o
learner completes stipulated laboratory activities.
Determine the structure of organic compounds with the use of Nuclear Magnetic
Resonance Spectroscopy (NMR).
Learning objectives
What you will learn as you master the competency:
a.
Given a structure, determine which protons are equivalent and which are nonequivalent;
predict the number of signals and their approximate chemical shifts.
b.
Use the integral trace to determine the relative numbers of different types of protons.
c.
Predict which protons in a structure will be magnetically coupled, and predict the number
of peaks.
d.
Use proton spin-spin splitting patterns to determine the structure of alkyl and other
groups.
e.
Draw the general features of the NMR spectrum of a given compound.
f.
Predict the approximate chemical shifts of carbon atoms in a given compound.
g.
Combine information from NMR, IR, and MS spectra to determine the structures of
organic compounds.
Performance Standards
Competence will be demonstrated:
o
through completion of a weekly laboratory report.
o
through successful completion of periodic written examinations.
o
Criteria - Performance will be satisfactory when:
o
learner completes assigned homework.
o
learner participates in class activities.
o
learner completes stipulated laboratory activities.
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12.
Consider the unique properties of conjugated systems and methods used to detect them
(UV spectroscopy)
Learning objectives
What you will learn as you master the competency:
a.
Show how to construct the molecular orbitals of ethylene, butadiene, and the allylic
system.
b.
Show the electronic configurations of ethylene, butadiene, and the allyl cation, radical,
anion.
c.
Recognize reactions that are enhanced by resonance stabilization of the intermediates.
d.
Develop mechanisms to explain the enhanced rates of observed products.
e.
Predict the products of Diels-Alder reactions.
Performance Standards
Competence will be demonstrated:
o
through completion of a weekly laboratory report.
o
through successful completion of periodic written examinations.
Criteria - Performance will be satisfactory when:
13.
o
learner completes assigned homework.
o
learner participates in class activities.
o
learner completes stipulated laboratory activities.
Visualize the structure and properties of aromatic compounds.
Learning objectives
What you will learn as you master the competency:
a.
Construct the molecular orbitals of a cyclic system of p orbitals similar to benzene and
cyclobutadiene.
b.
Use the polygon rule to draw the energy diagram for a cyclic system of p orbitals, and fill
in the electrons to show whether a given compound or ion is aromatic or antiaromatic.
c.
Use Huckel's rule to predict whether a given annulene, heterocycle, or ion will be
aromatic, antiaromatic, or nonaromatic.
d.
Name aromatic compounds and draw their structures from the names.
e.
Use IR, NMR, UV, and mass spectra to determine the structures of aromatic
compounds.
f.
Given an aromatic compound, predict the important features of its spectra.
Performance Standards
Competence will be demonstrated:
o
through completion of a weekly laboratory report.
o
through successful completion of periodic written examinations.
Criteria - Performance will be satisfactory when:
o
learner completes assigned homework.
o
learner participates in class activities.
o
learner completes stipulated laboratory activities.
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14.
Demonstrate the reactions of aromatic compounds.
Learning objectives
What you will learn as you master the competency:
a.
Predict products and give mechanisms for the common electrophilic aromatic
substitutions: halogenation, nitration, sulfonation, and Friedel-Crafts alkylation and
acylation.
b.
Draw resonance structures for the sigma complexes resulting from electrophilic attack
on substituted aromatic rings.
c.
Predict the position(s) of electrophilic aromatic substitution on molecules containing
substituents on one or more aromatic rings.
d.
Design syntheses that use the influence of substituents to generate the correct isomers
of multisubstituted aromatic compounds.
e.
Predict the products of Birch reduction, hydrogenation, and chlorination of aromatic
compounds.
Performance Standards
Competence will be demonstrated:
o
through completion of a weekly laboratory report.
o
through successful completion of periodic written examinations.
Criteria - Performance will be satisfactory when:
o
learner completes assigned homework.
o
learner participates in class activities.
o
learner completes stipulated laboratory activities.
Types of Instruction
Classroom Lecture
Discussion
Cooperative Learning Activities
Multi-Media Presentations
Laboratory Activities
Grading Information
Grading Rationale
Exams will be given after every 2 or 3 chapters in the textbook. Laboratory activities will be held each
week. Laboratory notebooks will be turned in and graded each week. A post test will be given at the end
of the semester.
Category Weights
Pre-test:
0%
Homework:
15%
Laboratory activities:
25%
Exams:
50%
Post Test:
10%
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General Organic Chemistry I
Grading Scale
A
90-100%
B
80-89%
C
65-79%
D
50-64%
F
0-59%
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General Organic Chemistry I