Syllabus for CHEMISTRY 2010 at
ORGANIC CHEMISTRY I
DESCRIPTION: A study of the preparations, properties,
nomenclature and
reactions of aliphatic compounds including alkanes, alkenes, cycloalkanes, cycloalkenes,
and alcohols. PREREQUISITE: CHEM 1120
with a grade of C or better. Three lecture,
three
laboratory hours per week.
GENERAL
INFORMATION: Organic Chemistry
is a transferable college level sequence
which is required in many science programs including pre-medicine,
pre-dentistry, pre-engineering, pre-pharmacy, and pre-veterinary
medicine. Consequently, it is a
comprehensive survey of the field of
organic chemistry with considerable stress placed on the classes,
structures,
nomenclature, and reactions of organic compounds.
INSTRUCTOR: James P. Neilan
office:J – 101K
email: james.neilan@volstate.edu
phone: 230-3357
Required Materials:
Textbooks: Organic Chemistry 1st or 2nd Edition by Janice Gorzynski Smith (McGraw Hill) with Molecular Models (First Edition of Smith can be used in place of the second edition)
Lab Notebook: A bound notebook with carbonless alternating blue and yellow headings. Available from the bookstore
The Organic Chem Lab Survival Manual by James Zubrick
Supplemental Materials:
Scientific
Calculator.
Student Guide and Solution
Manual: On
reserve in the Library and available from the Bookstore
ACD
ChemSketch 8.0 Freeware (can be downloaded from http://www.acdlabs.com/download/chemsk.html
)
Prohibited items:
Include any electronic or other
noise- or
light-emitting device that can distract or disturb its owners or
others, such
as beepers, cell phones, palm pilots, laptop computers, games, and the
like. Cellular telephones are not to be used during class for any
purpose, including making or receiving calls, photographs, or text
messages, or
playing games. Students cannot wear
headphones or ear
buds in class. The instructor may exclude
any student
from the class in which a disturbance occurs. The
student is responsible for any missed material and class assignments
made
during his/her absence.
PRIMARY EDUCATIONAL GOALS: The primary
goal of this
course is to communicate a basic understanding of the nomenclature,
structure,
properties, and reactions of organic compounds; to gain knowledge and
insight
into the relationship between organic chemistry and related
disciplines; and to
learn the appropriate techniques for the preparation, isolation, and
physical
and chemical characterization of organic compounds.
PRIMARY EDUCATIONAL OUTCOMES: Students
successfully
completing this course will have demonstrated an acceptable level
of
understanding of the basic nomenclature, structure, properties,
and
reactions of organic compounds; and techniques required in the
preparation and
isolation of organic compounds. These
students will
have acquired an adequate background for the pursuit of additional
coursework
in chemistry and biochemistry.
OTHER GOALS: This course will advance continued improvement
of
communication skills; application of the scientific method; and
deductive
reasoning, particularly in the interpretation of laboratory data as it
relates
to basic theory and broad underlying principles.
OUTCOME STATEMENTS: Upon successful
completion of
this course, the student will have demonstrated an acceptable ability
to:
1.
Define
organic
chemistry.
2.
Define
molecular
formula and empirical formula
3.
Describe
quantitative elemental analysis of carbon, hydrogen, and halogens.
4.
Do
calculations
involving empirical formulas, molecular weight, and molecular formula
determination
5.
Describe
covalent
and ionic bonds
6.
Draw
Lewis Dot
structures of molecules and ions
7.
Understand
formal
charges
8.
Understand
the
concept of resonance forms
9.
Discuss
the roles
of resonance and unshared electron pairs as they relate to carbocation
stability.
10.
Predict
the shape
of molecules
11.
Understand
the
drawing conventions for organic molecules
12.
Recognize
isomerism and draw structural isomers from molecular formulas.
13.
Discuss
atomic
orbitals.
14.
Understand
electron configurations.
15.
Discuss
sp, sp2,
and sp3 hybridization.
16.
Predict
bond
polarities from electronegativities.
17.
Relate
structure
to physical properties such as melting point, boiling point, and
solubility.
18.
Understand
the
definition of acids and bases (Lewis vs
Bronsted-Lowry)
19.
Understand
the
factors influencing acid strength
20.
Write
the
reaction between an acid and base
21.
Describe
common
functional groups.
22.
Predict
the
relative strength of intermolecular forces and the effect on physical
properties of compounds
23.
Describe
the
structure of alkanes
24.
Give
common names
and IUPAC nomenclature for the alkanes
25.
Discuss
the
significance of free rotation about the carbon-carbon single bond.
26.
Discuss
the
concepts of conformations and torsional strain.
27.
Understand
the
terms ‘staggered, eclipsed, and gauche’
28.
Predict
the
relative stability of alkane conformers
29.
Discuss
the
structure of cycloalkanes
30.
Describe
the
chair and boat conformations of cyclohexane
31.
Understand
the
concept of equatorial and axial positions on cyclohexane rings.
32.
Describe
combustion of alkanes
33.
Define
stereochemistry and stereoisomerism
34.
Understand
constitutional isomerism and stereoisomerism
35.
Understand
the
concept of chirality.
36.
Understand
the
structural relationship of enantiomers.
37.
Discuss
enantiomers and optical activity.
38.
Be
able to
determine the stereogenic configuration of chiral centers according to
the
Cahn, Ingold, Prelog
convention.
39.
Define
and
recognize diastereomers.
40.
Define
and
recognize meso structures.
41.
Be
able to
specify configurations in compounds with more than one chiral center.
42.
Describe
the
reactions of chiral molecules.
43.
Calculate
optical
purity from polarimetry data.
44.
Understand
the
concepts of racemic vs enantiomerically
enriched mixtures.
45.
Understand
the
concept of asymmetric synthesis.
46.
Understand
the
principles of mass spectrometry
47.
Determine
structural features from the fragmentation pattern of mass spectra
48.
Understand
the
principles of infrared (IR) spectroscopy
49.
Determine
the
functional groups present in a molecule from the infrared spectrum
50.
Understand
the
concepts of heat of reaction, energy of activation, and reaction
diagrams
51.
Discuss
the
characteristics of addition reactions, elimination reactions and
substitution
reactions.
52.
Understand
homolytic and heterolytic bond breaking
53.
Understand
the
use of bond dissociation energies in estimating heats of reaction.
54.
Understand
the
concepts of enthalpy and entropy
55.
Calculate
equilibrium constants from free energy changes.
56.
Understand
the
factors influencing rates of reaction.
57.
Describe
the
structure of the methyl radical.
58.
Discuss
the concepts
of transition state and reaction intermediates.
59.
Describe
the
characteristics of single step and multi-step reactions.
60.
Describe
the
classification and nomenclature of alkyl halides.
61.
Describe
the
physical properties of alkyl halides.
62.
Write
equations
for the preparation of alkyl halides.
63.
Describe
nucleophilic aliphatic substitution.
64.
Discuss
the
properties of nucleophiles and leaving groups.
65.
Understand
the
trends influencing nucleophilicity of the halides.
66.
Describe
first-order and second-order kinetics.
67.
Discuss
the SN2
reaction: mechanism and kinetics.
68.
Describe
the SN2
reaction: stereochemistry and reactivity.
69.
Discuss
the SN1
reaction: mechanism, kinetics, and stereochemistry.
70.
Discuss
protic
and aprotic solvents.
71.
75.Discuss
the effects
of solvents on the rates of SN1 and SN2
reactions
72.
Describe
the
significance of the rate-determining step on reaction mechanisms.
73.
Discuss
the
74.
Discuss
the
formation and structure of carbocations.
75.
Explain
the
relative stabilities of carbocations.
76.
Explain
the
rearrangement of carbocations.
77.
Describe
and
illustrate nucleophilic substitution in allylic and vinylic substrates
78.
Write
equations
for the preparation of alkenes by dehydrohalogenation of alkyl halides.
79.
Discuss
the
kinetics of dehydrohalogenation.
80.
Compare
and
contrast the E1 mechanism and the E2 mechanism.
81.
Describe
experimental evidence for the E1 and E2 mechanisms.
82.
Discuss
Zaitsev’s Rule
83.
Understand
the
orbital consequences of ‘anti-periplanar
orientation’
in the transition state of E2 eliminations
84.
Compare
the
factors that favor elimination versus substitution reactions.
85.
Describe
the
structure of alcohols and ethers.
86.
Describe
the
classification of alcohols.
87.
Give
common names
and IUPAC nomenclature of alcohols.
88.
Discuss
physical
properties of alcohols.
89.
Describe
the
preparation of alcohols.
90.
Describe
the
dehydration of alcohols with acids
91.
Describe
the
dehydration of alcohols with other dehydrating agents..
92.
Describe
alcohols
as acids and bases.
93.
Understand
the
structure and nomenclature of ethers and epoxides.
94.
Describe
the
physical properties of ethers.
95.
Write
equations
for the preparation of ethers.
96.
Describe
the
Williamson synthesis of ethers
97.
Write
equations
for the reactions of ethers with acids.
98.
Describe
the IR of alcohols and ethers.
99.
Describe
the
reaction of epoxides with nucleophiles under acid and base catalysis.
100.
Discuss
the
structure of alkenes and the carbon-carbon double bond.
101.
Be
able to name
alkenes by the IUPAC system.
102.
Be
able to give
common names for the lower alkenes.
103.
Describe
the
physical properties of alkenes.
104.
Write
equations
for addition reactions involving the carbon-carbon double bond.
105.
Relate
heat of
hydrogenation to alkene stability.
106.
Describe
and
discuss addition reactions in general.
107.
Discuss
the
mechanism of rearrangements in electrophilic addition reactions.
108.
Describe
the
mechanism of addition of halogens to alkenes.
109.
Describe
Markovnikov's rule as it relates to the addition of electrophiles to
alkenes.
110.
Describe
the
hydration of alkenes by oxymercuration.
111.
Describe
the
conversion of alkenes to alcohols by hydroboration.
112.
Describe
the
formation of 1,2-diols.
113.
Describe
the
determination of structure by ozonolysis.
114.
Discuss
the strucuture of alkynes
115.
Understand
the
nomenclature of alkynes
116.
Describe
the
addition of halogens to alkynes.
117.
Describe
the
reaction of electrophiles with alkynes.
118.
Explain
the
concepts of oxidation and reduction as it applies to organic molecules
119.
Recognize
oxidizing and reducing agents
120.
Understand
the
hydrogenation of alkenes and alkynes
121.
Determine
the
‘degrees of unsaturation’ of a compound from its molecular formula.
122.
Discuss
the stereochemical consequences of the
reduction of alkynes to
alkenes.
123.
Understand
the
terms ‘syn’ vs
‘anti’
addition.
124.
Describe
the epoxidation of alkenes with peracids.
125.
Describe
syn and anti dihydroxylation
of
alkenes
126.
Describe
the
oxidation of alcohols with oxidation agents.
127.
Discuss
oxidation
of alcohols with
128.
Understand
oxidative cleavage of alkenes and alkynes
129.
Determine
structures of alkenes and alkynes from ozonolysis data.
130. Understand the key features of the Sharpless oxidation.
131.
Describe
the
free-radical halogenation of alkanes
132.
Describe
the mechanism
of hydrogen abstraction by radicals.
133.
Describe
the
mechanism of radical addition to alkenes.
134.
Discuss
orientation and reactivity as they relate to free-radical substitution
in
alkenes.
135.
Describe
allylic
rearrangements.
136.
Relate
the
stability of the allyl radical to resonance hybrid structures.
137.
Describe
the
bromination of alkenes by NBS.
138.
Describe
the
orbitals involved in allyl radical formation.
ASSESSMENT: The achievement of the primary goals of
this course
will be determined by the ongoing assessment of the stated outcomes. Student perception of the course goals and
outcomes will
be provided by evaluation of the course and the instructors of the
course by
means of faculty evaluation questionnaires.
Written and oral
communication
skills, ability to utilize the scientific method, and think deductively
will be
assessed by written examinations containing discussion questions and
the
interpretation of experimental data as it relates to basic theory and
fundamental principles.
Mastery of specific
outcomes will
be determined by lecture examinations, laboratory performance, and
laboratory
notebooks. Lecture examinations consist of various types of questions
which
measure the student's memory, comprehension, and application of basic
facts,
concepts, and principles. Laboratory notebooks and experimental results
will be
evaluated to assess the student's ability to perform appropriate
organic
laboratory techniques (microscale and traditional); and to understand
principles from laboratory experiments.
Grades: The
grades in
all chemistry courses are based on the following scale:
|
A |
90 - 100 |
|
|
B |
80 - 89 |
Above Average |
|
C |
70 - 79 |
Average |
|
D |
60 - 69 |
Below Average |
|
F |
0 - 59 |
Failing |
The student's grade in this chemistry course will be determined
according to the
following weighting scheme:
|
Exams, Quizzes,
and assignments: |
50 % |
|
Laboratory
reports and Laboratory Final: |
30 % |
|
Comprehensive
Final examination: |
20 % |
One requirement of the
course is
that every student takes the final examination. Failure to take
the final
examination will result in a grade of F for the course. In the case
where a
final examination is missed and the instructor has been notified in
advance, it
may be possible (at the discretion of the instructor) for the student
to
receive a grade of I. However, a grade of I must be converted to
another letter
grade by completing work prior to the end of the seventh week of the
succeeding
semester, otherwise the I will be automatically converted to a
grade of
F. Students will not be allowed to register for chemistry courses
on an
Audit basis.
Attendance:
Attendance at all
lecture and laboratory meetings is expected. Persistent unexcused
absences
exceeding 30% of the lecture meetings may result upon approval of the
instructor and with approval of the Dean of Instruction in the
Administrative
Withdrawal of the student from that class. See the College Catalog for
the last
day to withdraw from the course or the College without penalty, and for
a
further explanation of the Administrative Withdrawal Policy.
Make-up Exams: There
are no makeup exams. If an exam is missed, the final exam
will be
weighed to take the place of the missing exam. Subsequent missed
exams
will be assigned a zero
Make-up Labs:
There are no
makeup labs. However, you will have the opportunity to drop your
lowest
lab score. You can use this to drop your lowest grade or to
replace a lab
you were not able to attend. Any other missed labs will result in
a grade
of zero (0) for that lab.
Deficiencies: A
student who has an
average of D or F on work completed and evaluated up to
mid-semester will
receive a deficiency slip by mail indicating the need for improvement
if a
course grade of C or better is to be achieved. If a student receives a
deficiency slip, he/she should explore with the instructor the wisdom
of
dropping or continuing in the course.
Cheating:
Cheating on a test
or exam will incur a grade of zero on that test or exam.
Recommended
Problems: These problems and
exercises are not to be handed in for grading, but it is not unusual
for
questions or problems similar to those assigned to appear on tests or
examinations.
Other Regulations: A
student is bound
by all rules and regulations appearing in the Student Handbook.
AMERICANS WITH
DISABILITIES ACT
STATEMENT: It is the
student’s
responsibility to self-identify with the Office of Disability Services
to
receive accommodations and services in accordance with The Americans
with
Disabilities Act (ADA). Only those students with appropriate
documentation
and who are registered with the Office of Disability Services will
receive
accommodations. For further information, contact the Office of
Disability
Services at (615) 230-3472, TDD
(615)-230-3488, or
visit the office which is located in Room 108 Wood Campus Center.
Equal
Opportunity Statement: Volunteer State
Community College is an equal opportunity Affirmative Action
Educational
Institution. No person shall be excluded from participation in,
be denied
the benefit of, or be subjected to discrimination under any program or
activity
of the College because of race, color, national origin, age, or
handicap.
The College also complies with the Age Discrimination in Employment Act
of
1967, as amended and with the
(Updated,
8/08/2008, J. Neilan)