Syllabus for CHEMISTRY 2020 at
ORGANIC CHEMISTRY II (4)
Description: A study of the nomenclature, properties, preparation, and
reactions of dienes, aldehydes, ketones, carboxylic acids and derivatives,
amines, and aromatic compounds. Three lecture hours and three laboratory
hours per week.
Prerequisite: CHEM 2010 with a grade of C or better
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, reactions, and synthesis of organic compounds.
Instructor: Dr. James P. Neilan
email:
phone: 230-3357
office: J-101K
(Office hours will be posted outside the door by the second week of the semester)
Required Materials:
Textbooks: Organic Chemistry 1st Edition by Janice Gorzynski Smith (McGraw Hill)
Molecular
Models: (Available at cost from the
storeroom)
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
Scientific Calculator.
Student Guide and Solution Manual: On reserve in the Library and available from the Bookstore
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 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:
OUTCOME STATEMENTS
1.
Describe the
free-radical halogenation of alkanes
2.
Describe the
mechanism of hydrogen abstraction by radicals.
3.
Describe the
mechanism of radical addition to alkenes.
4.
Discuss
orientation and reactivity as they relate to free-radical substitution in
alkenes.
5.
Describe allylic
rearrangements.
6.
Discuss the
concept of resonance.
7.
Relate the
stability of the allyl radical to resonance hybrid structures.
8.
Describe the
bromination of alkenes by NBS.
9.
Describe the
orbitals involved in allyl radical formation.
10.
Discuss and
illustrate hyperconjugation in alkyl radicals and alkyl cations.
11.
Understand the
nomenclature of dienes.
12.
Understand the
term conjugated.
13.
Determine the
order of stability of related dienes.
14.
Describe methods
of preparing dienes.
15.
Describe the
bonding in conjugated dienes using principles of valence bond
and molecular orbital theory.
16.
Distinguish
between 1,2 and 1,4 addition of electrophiles to dienes
17.
Use resonance
forms to predict the products of addition of electrophiles to dienes.
18.
Discuss the concept
of thermodynamic vs. kinetic control of reaction products.
19.
Discuss the
Diels-Alder reaction and the concept of pericyclic
reactions
20.
Distinguish
between endo and exo
stereochemistry.
21.
Define the role
of a dienophile in the Diels Alder reaction..
22.
Understand the
effect of inductive effects on the reactivity of dienophiles
23.
Understand the
concept of s-trans and s-cis conformations of dienes.
24.
Describe the
mechanism for the formation of polymers from dienes.
25.
Describe the
electronic transitions involved in ultraviolet (electronic) spectroscopy
26.
Use Beer's Law to
determine the concentration of a solute in solution.
27.
Understand the
relationship between structure and electronic spectra.
28.
Understand the
concept of aromaticity
29.
Give the common
and IUPAC names for aromatic compounds
30.
Understand the
terms ortho, para,
and meta as they apply to aromatic compounds..
31.
Understand the
mechanism of electrophilic substitution reactions of aromatic compounds.
32.
Discuss the
concept of directing groups in electrophilic substitution reactions of aromatic
compounds.
33.
Use the concept
of resonance to predict the product of an electrophilic substitution reaction
of an aromatic compound.
34.
Describe the
structure of aromatic compounds in terms of molecular orbital theory.
35.
Understand the Huckle rule for predicting aromaticity or anti-aromaticity.
36.
Discuss the
aromaticity of heterocyclic compounds.
37.
Recognize
substitution patterns of aromatic compounds from the infra-red spectra.
38.
Recognize the
characteristic UV absorptions of aromatic compounds
39.
Discuss the NMR
chemical shifts characteristic of aromatic compounds
40.
Recognize
activating and deactivating groups for aromatic electrophilic substitution
reactions.
41.
Predict the
directing effect of substituents in aromatic electrophilic substitution
reactions.
42.
Describe
inductive and resonance effects in substitution reactions of aromatic
compounds.
43.
Write reaction
products for the reaction of aromatic compounds with electrophiles.
44.
Understand the
mechanism of Friedel Craft alkylation of aromatic
compounds.
45.
Discuss the
concept of hydride and alkyl group shifts in alkylation reactions.
46.
Understand the
mechanism of Friedel Craft acylation
of aromatic compounds
47.
Describe the
Wolf-Kishner reaction.
48.
Describe the Clemmensen reduction.
49.
Use additive effects
to predict products of substitution reactions of di-substituted
aromatic compounds.
50.
Understand the
concept of nucleophilic substitution of aromatic compounds.
51.
Understand the
concepts of benzyne intermediates in
elimination/addition mechanisms of aromatic compounds.
52.
Write reactions
for the side chain oxidation of aromatic compounds.
53.
Discuss the
mechanism for the halogenation of aromatic side chains.
54.
Develop synthetic
strategies for the synthesis of trisubstituted
aromatic compounds.
55.
Understand the concept
of retrosynthetic strategy for planning
multistep synthesis
56.
Understand the
nomenclature of carboxylic acids.
57.
Explain the
effect of substituents on the acid strength of carboxylic acids.
58.
Discuss the
substituent effects on the acid properties of carboxylic acids.
59.
Identify the
different classes of carboxylic acid derivatives.
60.
Discuss the
nomenclature of acyl halides, anhydrides, esters and amides.
61.
Predict the
relative reactivity of carboxylic acid derivatives.
62.
Write the general
mechanism for nucleophilic acyl substitution reactions.
63.
Write reactions
for the preparation of carboxylic acid derivatives (acid halides, anhydrides,
esters, and amides)
64.
Understand the
concept of protecting groups in synthetic strategies.
65.
Understand the
nomenclature of aldehydes and ketones.
66.
Write reactions
for the oxidation of aldehydes to carboxylic acids.
67.
Understand the
use of DIBAH for the preparation of aldehydes.
68.
Discuss the use
of organocuprates in the preparation of ketones.
69.
Understand
reaction mechanisms for the nucleophilic addition reactions of aldehydes and
ketones.
70.
Discuss
reactivity patterns of aldehydes and ketones.
71.
Discuss methods
for the reduction of aldehydes and ketones.
72.
Understand the
use of Fischer projections for carbohydrates.
73.
Understand the
reaction of Grignard reagents with aldehydes, ketones, and esters.
74.
Understand the
use of acetals as protecting groups for carbonyl compounds.
75.
Understand
reaction mechanisms for imine and eneamine formation.
76.
Describe and
understand the mechanism of the Wittig reaction.
77.
Describe and
understand the mechanism of the Cannizarro reaction.
78.
Discuss 1,4 addition of nucleophiles to alpha-beta unsaturated
carbonyl compounds.
79.
Describe the IR
and NMR spectra of carbonyl compounds.
80.
Write reactions
for the preparation of carboxylic acids, including the carboxylation of
Grignard reagents.
81.
Write the reaction
for the reduction of carboxylic acids with LAH.
82.
Discuss the
dehydration of amides to produce nitriles.
83.
Understand the
reaction mechanism for the hydrolysis of nitriles.
84.
Discuss the
reactions of nitriles to form ketones, amines, and amides.
85.
Understand the IR
and NMR spectra of carboxylic acids and carboxylic acid derivatives..
86.
Understand the
reaction mechanism for nucleophilic acyl substitution reactions.
87.
Discuss the
structure of lactones and lactams.
88.
Discuss the role
of acyl phosphates and thioesters in biological systems.
89.
Understand the
process of step-growth polymerization.
90.
Understand the
reaction mechanism for the enolization of a ketone or aldehyde.
91.
Understand the
reaction mechanism for the alpha halogenation of a ketone or aldehyde.
92.
Discuss the Hell-Vollhard-Zelinskii Reaction.
93.
Describe the
formation of enolates in terms of acid - base chemistry.
94.
Discuss the use
of LDA in the formation of enolates.
95.
Describe the
chemistry of enolates with electrophiles.
96.
Understand C vs.
O alkylation of enolates.
97.
Describe the
haloform reaction.
98.
Understand the
mechanism of the malonic ester synthesis.
99.
Understand the
mechanism of the acetoacetic ester synthesis.
100.
Describe the
direct alkylation of enolates.
101.
Understand the
mechanism of the aldol reaction.
102.
Understand the mechanism
of the Claisen and Dieckmann condensation reactions.
103.
Understand the
mechanism of the Michael reaction.
104.
Understand the
mechanism of the Stork eneamine reaction.
105.
Describe the
Robinson annulation method for the synthesis of cyclic molecules.
106.
Understand the
nomenclature of amines
107.
Describe the
concept of pyramidal inversion and the consequences for chirality in
amines.
108.
Describe the
properties of amines.
109.
Write reactions
for the synthesis of amines.
110.
Describe the
Gabriel synthesis of primary amines.
111.
Describe the
reductive amination of carbonyl compounds.
112.
Understand the
mechanisms of the Hoffman and Curtius rearrangements.
113.
Describe the
Hoffman elimination
114.
Understand the
terms Hoffman product and Zaitsev
product.
115.
Understand the
directing effect of the amine group in aromatic electrophilic substitution
reactions.
116.
Describe a diazonium salt and its use in the Sandmeyer
reaction.
117.
Describe the
diazo coupling reaction to form azo dyes.
118.
Understand the
concept of phase transfer catalysis.
119.
Understand the IR
and NMR spectra of amines.
120.
Identify unknown
compounds using IR, NMR and MS spectral data.
121.
Develop synthetic
strategies using the reactions covered in the syllabus
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, assignments, 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:
|
Lecture: (Exams, Quizzes and Assignments) |
50 % |
|
Laboratory reports (25%) and Laboratory Final (5%): |
30 % |
|
Comprehensive Final examination: |
20 % |
Completion of the final exam is a requirement of this course. 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.
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 Vice President of Academic Affairs 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 one exam is missed for a valid reason, the final exam will be weighted to compensate for the missed exam. Any other missed exams will result in a grade of zero (0) for that exam.
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.
Cheating: Cheating on a test or exam will incur a grade of zero (0) on that test or exam.
Recommended Problems: These problems and exercises may be handed in for grading upon the direction of your instructor. 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.
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, 4/13/2008, J. Neilan)