Syllabus for CHEMISTRY 2010 at
ORGANIC CHEMISTRY I (4)
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, structu
office: J
– 101C
email:
parris.powers@volstate.edu
phone: 230-3703
Required Materials:
Textbooks: Organic Chemistry 1st Edition by Janice Gorzynski Smith (MdGraw Hill)
Lab Notebook: A bound notebook with carbonless alternating white and yellow pages. Available from the bookstore
Supplemental Materials:
The Organic Chem
Lab Survival Manual by James Zubrick
Molecular Models: (Available
at cost from the storeroom)
Scientific Calculator.
Student Guide and Solution
Manual: On
reserve in the Library and available from the Bookstore
ACD ChemSketch 10.0
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 principles of nuclear
magnetic resonance spectroscopy.
51. Define the concept of ‘chemical shifts’
52. Understand the nature of ‘spin-spin
spitting’
53. Determine molecular structural features by
interpretation of 1H
and 13C NMR.
54. Understand the concepts of heat of
reaction, energy of activation, and
reaction diagrams
55. Discuss the characteristics of addition
reactions, elimination
reactions and substitution reactions.
56. Understand homolytic and heterolytic bond
breaking
57. Understand the use of bond dissociation
energies in estimating heats of
reaction.
58. Understand the concepts of enthalpy and
entropy
59. Calculate equilibrium constants from free
energy changes.
60. Understand the factors influencing rates of
reaction.
61. Describe the structure of the methyl
radical.
62. Discuss the concepts of transition state
and reaction intermediates.
63. Describe the characteristics of single step
and multi-step reactions.
64. Describe the classification and
nomenclature of alkyl halides.
65. Describe the physical properties of alkyl
halides.
66. Write equations for the preparation of
alkyl halides.
67. Describe nucleophilic aliphatic
substitution.
68. Discuss the properties of nucleophiles and
leaving groups.
69. Understand the trends influencing
nucleophilicity of the halides.
70. Describe first-order and second-order
kinetics.
71. Discuss the SN2 reaction: mechanism and
kinetics.
72. Describe the SN2 reaction: stereochemistry
and reactivity.
73. Discuss the SN1 reaction: mechanism,
kinetics, and stereochemistry.
74. Discuss protic and aprotic solvents.
75. Discuss the effects of solvents on the
rates of SN1 and
SN2 reactions
76. Describe the significance of the
rate-determining step on reaction
mechanisms.
77. Discuss the
78. Discuss the formation and structure of
carbocations.
79. Explain the relative stabilities of
carbocations.
80. Explain the rearrangement of carbocations.
81. Describe and illustrate nucleophilic
substitution in allylic and
vinylic substrates
82. Write equations for the preparation of
alkenes by dehydrohalogenation
of alkyl halides.
83. Discuss the kinetics of
dehydrohalogenation.
84. Compare and contrast the E1 mechanism and
the E2 mechanism.
85. Describe experimental evidence for the E1
and E2 mechanisms.
86. Discuss Zaitsev’s
Rule
87. Understand the orbital consequences of
‘anti-periplanar
orientation’ in the transition state of E2 eliminations
88. Compare the factors that favor elimination
versus substitution
reactions.
89. Describe the structure of alcohols and
ethers.
90. Describe the classification of alcohols.
91. Give common names and IUPAC
nomenclature of
alcohols.
92. Discuss physical properties of alcohols.
93. Describe the preparation of alcohols.
94. Describe the dehydration of alcohols with
acids
95. Describe the dehydration of alcohols with
other dehydrating agents..
96. Describe alcohols as acids and bases.
97. Understand the structure and nomenclature
of ethers and epoxides.
98. Describe the physical properties of ethers.
99. Write equations for the preparation of
ethers.
100. Describe the Williamson synthesis of ethers
101. Write equations for the reactions of ethers
with acids.
102. Describe the IR
of alcohols and ethers.
103. Describe the reaction of epoxides with
nucleophiles under acid and base
catalysis.
104. Discuss the structure of alkenes and the
carbon-carbon double bond.
105. Be able to name alkenes by the IUPAC system.
106. Be able to give common names for the lower
alkenes.
107. Describe the physical properties of
alkenes.
108. Write equations for addition reactions
involving the carbon-carbon
double bond.
109. Relate heat of hydrogenation to alkene
stability.
110. Describe and discuss addition reactions in
general.
111. Discuss the mechanism of rearrangements in
electrophilic addition
reactions.
112. Describe the mechanism of addition of
halogens to alkenes.
113. Describe Markovnikov's rule as it relates
to the addition of electrophiles
to alkenes.
114. Describe the hydration of alkenes by oxymercuration.
115. Describe the conversion of alkenes to
alcohols by hydroboration.
116. Describe the formation of 1,2-diols.
117. Describe the determination of structure by
ozonolysis.
118. Discuss the strucuture
of alkynes
119. Understand the nomenclature of alkynes
120. Describe the addition of halogens to
alkynes.
121. Describe the reaction of electrophiles with
alkynes.
122. Explain the concepts of oxidation and
reduction as it applies to
organic molecules
123. Recognize oxidizing and reducing agents
124. Understand the hydrogenation of alkenes and
alkynes
125. Determine the ‘degrees of unsaturation’ of
a compound from its
molecular formula.
126. Discuss the stereochemical
consequences of
the reduction of alkynes to alkenes.
127. Understand the terms ‘syn’
vs ‘anti’ addition.
128. Describe the epoxidation
of alkenes with peracids.
129. Describe syn
and anti dihydroxylation
of alkenes
130. Describe the oxidation of alcohols with
oxidation agents.
131. Discuss oxidation of alcohols with
132. Understand oxidative cleavage of alkenes
and alkynes
133. Determine structures of alkenes and alkynes
from ozonolysis data.
134. Understand the key features of the Sharpless
oxidation.
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.
ADA
statement: In compliance with the Americans with
Disabilities Act,
students are encouraged to register with the Office of Student
Disability
Services for assistance with accommodations. It is the
student's
responsibility to self identify with the Office of Disability Services
in order
to receive accommodations. Disability Services is located in
C206B.
Only those students with official documentation from the Office of
Disability
Services will receive services.
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, 5/23/2008, P Powers)