CHM 2211C: Organic Chemistry II
4 cr.
Section: 286138
Fall
Term 2008
SITE: North Campus D-207 Lecture/D204 Lab
DAY/TIME: Lecture: Monday 7:00-10:00 p.m. D-207
Additional
Lecture Wednesday 7:00-10:00 p.m. D-TBA
(Dry Labs)
Wet Labs Wednesday 7:00-10:00 p.m. D-204 (6 TO 8)
Pretesting:
Monday and Wednesday 6:00-7:00 p.m. D203
or D-TBA
Pretesting: Monday and Wednesday 10:00-10:30 p.m. D203
or D-TBA
FCCJ Course Description:
This course, a continuation of
Organic Chemistry I includes mechanisms of organic reactions, carbohydrates and
macromolecules. Six contact hours: three lecture hours, three laboratory hours.
A.A.
Prerequisites: CHM 2210C with a grade of
“C” or better.
Required
Textbooks:
Lecture Text,
Laboratory Text, Supplies, and Materials:
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Organic Chemistry, 6th Edition John
E. McMurry - ISBN-10: 0534389996 ISBN-13: 9780534389994 1376 Pages Casebound ©
2004 Published Price New: $? Used Price: $? CHM 2210C covers Chapters 1-12 CHM 2211C covers Chapter 13-24 Optional Chapters: Chapters 25-31 |
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Table of Contents |
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Structure and Bonding. CHM 2211C Organic
Chemistry II (Topics not covered in CHM 2210 Spring 2008J 9. Stereochemistry. 13. Structure
Determination: Nuclear Magnetic Resonance Spectroscopy 14. Conjugated Dienes and
Ultraviolet Spectroscopy. 17. Alcohols and Phenols. Optional Chapters |
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Laboratory Text: TBA or Weekly Printouts
Optional: Study Guide &
Student Solutions Manual
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This comprehensive manual provides
answers and explanations for all in-text and end-of-chapter exercises. It
also includes summaries of name reactions, functional-group synthesis and
reactions, lists of reagents and abbreviations, and articles on topics
ranging from infrared absorption frequencies to Nobel Prize winners in
chemistry. This edition includes expanded in-text problems, summary quizzes
for approximately every three chapters, more detailed explanations in solutions,
and chapter outlines ISBN:
0-534-40934-2. |
Goggles
or Visorgogs or use the ones in the cabinet
Instructor: John
T. Taylor About Me Resume
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Office:
D-270 Office
Phone: 904-766-6763 (leave messages) Cell Phone:
904-614-0531 Link
to site: http://www.fccj.us/OfficeF08.htm
for
current office hours The instructor is available for additional office
hours by appointment. Appointments
must be made at least two days in advance, except for extreme emergencies. Office hours are subject to change email: johtaylo@fccj.edu |
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E-Mail assignments to both
addresses below Subjects of emails must describe briefly
the assignments being submitted and begin with the # 2211: i.e. 2211:
First Email or 2211: your subject |
Email Requirement:
Each student should
send the instructor an email during the first week from both your FCCJ email
account and/or an outside email account for your primary contact, and the other
as a backup contact. Be certain you put in subject box:
2211: first email (only the students who did not have me for 2210)
Tell me
about yourself. Why are you taking this course? When did you
complete CHM 2046C, where, with which instructor, and your grade. What
is your highest math course completed? Where do you live? What are your
telephone numbers? What is your external email address which can serve as a
backup to FCCJ assigned email.
Always begin the subject
of each email with 2211:
Subject-less
emails will be deleted or subjects without the number code may be deleted.
Attachments will only be opened if the number code is in the subject line. This
prevents viruses and spam.
ATTENDANCE:
Students are expected to attend class and will be
responsible for all material presented. The student must sign the attendance
roster to earn credit for attendance.
Each on campus class attended will be worth one point,
New students will fill out a data card similar to your instructor one the last
page of this syllabus worth one point of the two points for the first day’s
attendance.
Free
Time Chart: Find me 10 hours per week of the 168 total: List them
Description: http://www.hccfl.edu/faculty/john_taylor/cgs1555/spring04/syllabus/freetime.htm
Free Time First Lab Exercise:
Chemistry takes a lot of time to study. Each student should identify at least 10
hours or more per week of free time that she/he will commit towards his/her
study of chemistry. The following are
suggested strategies for scheduling your study times. Make an hour by hour seven day matrix 8
columns (hour and each day of the week) by 24 lines (representing each hour).
See Master Student Web Site above. A
blank matrix has been attached to this syllabus for you to complete.
Starting
with wake-up and end with sleeping:
1.
Schedule fixed blocks of time first. These include work, class time, eating,
and sleeping.
2.
Include time for travel and errands
3.
Schedule time for fun.
4.
Set realistic goals.
5.
Allow flexibility in your schedule.
6.
Study at least two hours for every hour in class plus an extra two for computer
assignments in the open lab and an extra two with a cooperative group member
for homework comparison and checking.
7.
Avoid scheduling marathon study sessions.
8.
Set clear starting and stopping times.
9.
Plan for the Unplanned!
Study
Groups/Phone Network/Lab Partner:
On the first day of class each new student
will complete a Data Card, Interview a peer, and introduce (if time permits)
that peer to the class. From these exercises and the learning styles inventory,
study groups, a phone network, and lab partners need to be established. Study
areas, as well as the classroom, should be used for study group and lunch and
learn sessions. Some portions of the office times may meet in the library
computer learning lab. Each week volunteers will be appreciated to assist in
the group operation of the class. The first personal assistant volunteer will
prepare a matrix with each student’s free study time so that study groups may
begin to be formed the second week of school. The phone network will be
established so that in case of emergencies by the instructor each student will
be responsible to call two other students in the network to alert the student
of the emergency so that information may be distributed prior to the next
scheduled class. Emergencies will usually also include a group email on the
morning/afternoon of the class meeting.
E-Instruction (option):
During a scheduled class (150 minutes), after going through the lecture
on the assigned chapters via many modalities of teaching including Internet web
sites, the instructor will utilize either the last 10 minutes or the first 10
minutes of class to go through the power point for the assigned chapter as a
review.
However, multiple choice questions will be inserted into the online
power points which will require all students to answer via the instructor’s e-Instruction system (keypads). Each
correct response will be worth one point, while an incorrect response will
count zero points. e-Instruction system will be worth no more than 50
points (out of 100 possible) for the term (5% total if used Fall Term 2008) otherwise
the 5 % will be included in the Modular Exams
Students are expected to get
50% correct on each day’s e-Instruction
questions. During the term, the instructor may pretest a section of the
multiple choice for the course using the e-Instruction
system where the responses will count 1 point each of the 10 to 20 points
assigned to multiple choice for that Module.
Daily
Pretest Exam Pages (optional):
Pretest consisting of exam
pages may be administered before (6:00-7:00) class, sometimes during, and/or
after every class which is not a scheduled exam day. These pretest quizzes may not be made up outside of any other
class time, unless directed by the instructor to complete the pretest in the
test center during an assigned period of time.
Scored
pretest exam pages are NOT recorded in the instructor’s grade book or on
Blackboard, but must be attached to the Exam Grading Outline the
day of the exam to receive the pretest grade. This pretest packet is submitted
as a separate packet. Students must write the scores on both the cover sheet of
the pretest packet and on the front page of each exam.
The student
will skip the section of the chapter exam that is pre-tested. The Pretest scores sometimes may be recorded
on the attendance sheet, but only for your instructor’s sense of current levels
of class achievement. If you loose the graded pretests, you will have to do the
section over on the exam.
The instructor
only records Exam totals in his grade book and on Blackboard. Multiple Choice and the Textbook Short Answer Suggested Exam for that
chapter are usually only tested on exam day and are usually never pre-tested or
post-tested. (The MC may be tested via
e-Instruction)
Do Not Staple the Chapter Exams together as they are
graded separately, listed on Blackboard separately, and returned separately
after the exam day. Please staple carefully as directed. Mixing the chapter
papers on Exam day may result in a lower grade.
1. Pretest
exam pages are actual
pages of the exams. They are not open book. They are not open notes. They are
not collaboration with your neighbor.
2. The
pretests may NOT be used during the exam!
3. You
must do the pretests in class. You may NOT take the pretests home.
Samples of each
section (pretest) of each exam may sometimes be found on the grading outline on
the web site. On the sample tests are suggestions for paper and pencil homework
in the textbook. The grading outline may be found at:
http://www.fccj.us/chm2211/2211grdF08.htm
Pre-testing
is a privilege not a right!
Our classroom D-207 has a scheduled
class (CHM 2045) in the room before our class from 5:30-6:50 p.m.on Monday and Wednesday. Pretesting
will begin at 6:00 to 6:30 p.m. each class day and must be completed before
class begins at 7:00. The location of the pretesting
will be announced since the classroom is being used. Students who are late to
class (after 7:00 p.m.), will not be allowed to pretest until after class.
Student should plan to stay late if they can not arrive early. Many times the pretest
will not be administered till the last 5-25 minutes of class so that student
may complete the item after class has concluded.
Post-Testing:
The instructor may post test sections of the
modular exams that a majority of the students on designated days did not
succeed. Multiple choice, Suggested Short Answer Text Exams and vocabulary
sections may not be post-tested. The
designated last day for post testing is Saturday December 6 at a time to be
announced. The post test is a free attempt. Scoring lower on the post test than
on the modular exam section will not penalize the student. The post test will
be ignored and the exam section score will count. Improving on the post test
will replace that section’s score on the modular exam and the improvement will
raise the score of the modular test. A student scores 5 out of 10, post test
and scores 10 out of 10, The student’s grade is
improved by the net five points. . The student will resubmit his/her exam with
the graded post test stapled on top for an adjustment in the modular exam
score. If the
student does not have her/his exam, then post testing will NOT be possible.
MAKE-UP POLICY:
Make-up exams are usually not
given. In the event of an unavoidable absence on exam day (jury duty,
hospitalization, incarceration, and death in the immediate family), you will be
allowed make-up tests only upon the instructor’s approval..
You must contact the instructor, no later than, the week of the exam in order to
discuss what arrangements might be made. This may be done with a quick email. A message must be left on the instructor's e-mail
(johtaylo@fccj.edu ) if the instructor cannot be reached. If a makeup
is allowed, it must be completed prior to return of the exam papers completed
by the students attending the scheduled exam. Missed exams will otherwise count
as 0 points. Papers are returned usually after one or two weekends after the
exam.
Students who take the test on the assigned day are guaranteed to receive their graded exam on or before the next exam day, otherwise the student will be assigned a 100% grade for the un-graded paper. Students not taking the exam on the assigned exam day may not receive their grade until days or weeks after the class papers are returned.
A-16 Exam Schedule North Campus:
Exam #1 (Chapters 10, 15, 16) Wednesday (TBA either weeks 3 or 4)
Exam #2 (Chapters 17, 18) Wednesday TBA (either weeks 6 or 7)
Exam #3 (Chapters 19, 20, 21) Wednesday TBA (either weeks 12 or
13)
Exam #4 (Chapters 22, 23, 24, portions of 25, 26, 27 ) Wednesday week 16
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Major Learning Outcomes
(Goals): This course is designed as the second
semester of a two semester sequence of Organic Chemistry. CHM 2211C has been modified and streamlined
to accomplish the following major learning outcomes in 45-60 total hours of
class and instruction. Students entering the class should have had CHM 2210C
with a passing grade and a working knowledge of bonding concepts and chemical
kinetics from General Chemistry and have a knowledge of structure, reactions
and mechanisms of Alkanes, Alkenes, and Alkynes. |
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Chemistry 2211 Organic
Chemistry II General Learning Objectives
Students who complete Organic Chemistry II
(CHEM 2211) are expected to demonstrate knowledge of the following general
learning objectives.
- Students should have specific knowledge of the concepts of organic chemistry.
- Students should be able to cite applications of the concepts of organic chemistry.
- Students should be able to work chemistry problems that involve synthetic and mechanistic pathways.
- Students should have organic chemistry laboratory skills.
- Students should have computer and internet skills
Chemistry 2211 Organic
Chemistry II Specific Learning Objectives
Students who complete Organic Chemistry I
(CHEM 22110) are expected to demonstrate knowledge of the following
content-based learning objectives. The
learning objectives are arranged by major content area.
X. Stereochemistry (Chapter 9) (from 2210C
Review)
Students
must know or be able to do the following:
·
Define, identify,
and draw enantiomers.
·
Define chiral and achiral.
·
Distinguish
between chiral and achiral
objects.
·
Assign centers
within a molecule as chiral or achiral.
·
Define the terms
- plane polarized light, optically active, polarimeter,
levorotatory, and dextrorotatory.
·
Sketch a
representation of a polarimeter.
·
Describe how enantiomers respond to plane polarized light.
·
Define specific
rotation.
·
Describe
Pasteur's discovery of enantiomers.
·
Compare and
contrast the physical properties of a pair of enantiomers.
·
Apply Cahn-Ingold-Prelog sequence rules to chiral
centers.
·
Assign R and S
configurations to enantiomers.
·
Define, identify,
and draw diastereomers.
·
Compare and
contrast the physical properties of diastereomers to
those of enantiomers.
·
Define, identify,
and draw a meso compound.
·
Use the formula 2n
to determine the maximum number of stereoisomers.
·
Define racemic mixture.
·
Describe how a racemic mixture can be resolved.
·
Compare and
contrast the physical properties of enantiomers, a meso compound, and a racemic
mixture of the two enantiomers.
·
Draw Fischer
projections.
·
Predict the
stereochemistry of the product in the addition of HBr
to alkenes.
·
Predict the
stereochemistry of the product in the addition of Br2 to alkenes.
·
Predict the
stereochemistry of the product in the addition of HBr
to a chiral alkene.
·
Discuss chirality in other atoms such as nitrogen.
·
Be familiar with
the difference in biological properties (such as different odors or tastes)
that a pair of enantiomers may have.
· Be familiar with the difference in biological properties that a pair of stereoisomers may have.
XI. Akyl
Halides (Chapter 10) (from 2210C Review)
Students
must know or be able to do the following:
·
Define alkyl
halides and be familiar with some examples.
·
Use IUPAC nomenclature
rules to name alkyl halides.
·
Describe the electrophilic behavior exhibited by alkyl halides.
·
Know and apply
the preparation of alkyl halides via radical halogenation
of alkanes - reaction and mechanism.
·
Predict and
explain the observed reactivity order of alkane hydrogens toward radical chlorination/bromination.
·
Calculate the
predicted product ratios from the monochlorination of
an alkane.
·
Know and apply an
allylic bromination with
NBS - reaction and mechanism.
·
Explain why bromination with NBS occurs exclusively at an allylic position.
·
Know the
stability order of various radicals including vinylic,
allylic, methyl, primary, secondary, and tertiary.
·
Define
delocalized.
·
Draw resonance
structures for allyl radicals.
·
Know and apply
the reaction of the products of an allylic bromination with KOH to undergo a dehydrohalogenation
to form a diene - reaction only.
·
Know and apply
the reaction of alcohols with HX to form alkyl halides - reaction only.
·
Compare the
reactivity of primary, secondary, and tertiary alcohols with HX.
·
Know and apply
the reaction of primary and secondary alcohols with SOCl2 and PBr3
to form alkyl halides - reaction only.
·
Describe how Grignard reagents are formed.
·
Describe the
electronic and basic nature of the Grignard reagent.
·
Know and apply
the reaction of a Grignard reagent with water-
reaction only.
·
Know and apply
the preparation of a Gilman reagent - reaction only.
·
Know and apply
the reaction of Gilman reagent with an alkyl halide- reaction only.
·
Define oxidation
and what occurs during an organic oxidation reaction.
·
Define reduction
and what occurs during an organic reduction reaction.
·
Rank compounds
according to their oxidation level.
XII.
Reactions of Alkyl Halides:
Nucleophilic
Substitutions and Eliminations (Chapter 11)
Students must know or be able to do the
following:
·
Define and write
a general mechanism for a sustitution and an
elimination reacion of an alkyl halide.
·
Be familiar with
the discovery of the Walden Inversion.
·
Know and apply
the key ideas relating to SN1 and SN2 reactions including
their stereochemistry and kinetics.
·
Know and apply
the reactions and mechanisms of SN1 and SN2 reactions.
·
Define substrate.
·
Know and apply
the characteristics of SN1 and SN2 reactions including
substrate reactivity, nucleophile reactivity, leaving
group reactivity, and solvent reactivity.
·
Describe the
characteristics that affect nucleophilicity.
·
Compare and
contrast the dielectric polarizations of protic and aprotic solvents.
·
Be able to site
examples of protic and aprotic
solvents.
·
Define and apply Zaitsev’s rule.
·
Know and apply
the key ideas relating to E1 and E2 reactions including their stereochemistry
and kinetics.
·
Know and apply
the reactions and mechanisms of E1 and E2 reactions.
·
Define periplanar and syn periplanar, and anti periplanar.
·
Describe how cyclohexane conformation affects reactivity in elimination
reactions.
·
Describe the
deuterium isotope effect in relation to providing support of an E2 mechanism.
·
Predict whether
an SN1, SN2, E1, or E2 will occur based on reaction
characteristics such as substrate, nucleophile, and
solvent.
·
Describe
reactions in which substitution mechanisms are utilized (such as acetylide ion alkylations and
conversion of alcohols into alkyl halides).
Students must know or be able to do the
following:
·
Define and
identify conjugated dienes.
·
Be familiar with
the methods available for the preparation of conjugated dienes.
·
Be able to
discuss and explain the stability of conjugated dienes.
·
Be able to
describe conjugated dienes from a molecular orbital
standpoint.
·
Discuss the
structure and bonding in conjugated dienes.
·
Know and apply electrophilic addition reactions to conjugated dienes- reaction and mechanism.
·
Explain and apply
kinetic versus thermodynamic control of reactions.
·
Be familiar with
polymers formed from conjugated dienes.
·
Know and apply
the Diels-Alder reaction- reaction and mechanism.
·
Be able to
discuss the dienophile and diene
portions of a Diels-Alder reaction.
·
Be able to
discuss the stereochemistry of the product in a Diels-Alder
reaction.
II. Benzene and Aromaticity (Chapter 15)
Students
must know or be able to do the following:
·
Define aromaticity and identify aromatic organic molecules.
·
Be familiar with
the sources of aromatic hydrocarbons.
·
Know the
structure and common names for selected aromatic molecules.
·
Be able to name
aromatic compounds using the IUPAC rules for nomeclature.
·
Discuss the
structure and stability of benzene and other common aromatic molecules.
·
Describe benzene
from a molecular orbital standpoint.
·
Explain and apply
the 4n +2 rule for predicting aromaticity.
·
Be familiar with
aromatic ions and anti-aromatic molecules.
·
Be able to apply
the concepts of aromaticity to aromatic heterocylces and polycyclic molecules.
· Be able to understand and interpret the Infrared and Nuclear Magnetic Resonance spectra of aromatic molecules.
III. Chemistry of
Benzene: Electrophilic Aromatic Sustitution
(Chapter 16)
Students
must know or be able to do the following:
· Write a general mechanism for electrophilic aromatic substitution.
· Know and apply the halogenation of aromatic rings- reaction and mechanism.
· Know and apply the nitration of aromatic rings- reaction and mechanism.
· Know and apply the sulfonation of aromatic rings- reaction and mechanism.
· Know and apply the Friedel-Crafts alkylation and acylation of aromatic rings- reactions and mechanisms.
· Predict how a substituent on a ring impacts on further substitution of that ring, including orientation and rate of reaction
· Define and explain the difference between inductive and resonance effects.
· Be able to decide if resonace or inductive effects are dominant in an electrophilic aromatic substitution.
· Predict whether a substituent is an activator or deactivator in electrophilic aromatic substitution.
· Predict whether a substitutent is an ortho-/para- or meta- director in electrophilic aromatic substitution.
· Draw resonance structures to predict and explain how an existing substituent impacts on further electrophilic aromatic substitution.
· Predict and explain the directing effects of disubstituted aromatic rings towards further substitution.
· Know and apply the nucleophilic aromatic substitution reaction of aromatic compounds- reaction and mechanism.
· Be familiar with the structure, generation and reactions of benzyne.
· Know and apply the oxidation of alkyl side chains of aromatic compounds.
· Know and apply the bromination of alkyl side chains of aromatic compounds.
· Know and apply the reduction of aromatic compounds.
· Be able to carry out the synthesis of polysubstituted aromatic molecules.
IV. Alcohols and
Phenols (Chapter 17)
Students
must know or be able to do the following:
·
Define and
identify an alcohol and a phenol.
·
Be familiar with
the industrial preparation of alcohols and phenols.
·
Be able to name
an alcohol using the IUPAC rules for nomenclature.
·
Be familiar with
the structures and common names of selected alcohols.
·
Be able to name
phenols.
·
Be familiar with
the physical properties of alcohols and phenols including: hydrogen bonding,
acidity and basicity.
·
Be familiar with
the reduction of carbonyl compounds (including carboxylic acids and their
derivatives) to produce alcohols.
·
Be familiar with
the addition of Grignard reagents to carbonyl
compounds (including carboxylic acids and their derivatives) to produce
alcohols.
·
Be familiar with
the limitations of the addition of Grignard reagents
to carbonyl compounds.
·
Know and apply
the dehydration of alcohols to afford alkenes- reaction and mechanism.
·
Know and apply
the conversion of alcohols into alkyl halides- reactions and mechanisms.
·
Know and apply
the conversion of alcohols into tosylates- reaction
and mechanisms.
·
Know and apply
the oxidation of alcohols to afford carbonyl compounds- reactions and
mechanisms.
·
Know and apply
the protection and deprotection of alcohols-
reactions and mechanisms.
·
Be familiar with
the industrial methods for the preparation of and uses of phenols.
·
Be familiar with
the oxidation of phenols to afford quinones.
· Be able to understand and interpret the Infrared, Mass Spectroscopy and Nuclear Magnetic Resonance spectra of alcohols and phenols.
V. Ethers, Epoxides, Thiols, and Sulfides (Chapter 18)
Students
must know or be able to do the following:
·
Define and
identify an ether and an epoxide.
·
Be familiar with
the structures and trivial names of common ethers.
·
Be familiar with
the structure, properties, and sources of ethers.
·
Know and apply
the Williamson Ether Synthesis- reaction and mechanism.
·
Know and apply
the alkoxymercuration of alkenes for the preparation
of ethers- reaction and mechanism.
·
Know and apply
the acidic cleavage of ethers-reaction and mechanism.
·
Be familiar with
the Claisen rearrangement.
·
Be familiar with
and able to use the methods available for the preparation of epoxides.
·
Be familiar with
and able to use the ring opening reaction of epoxides
under both acidic and basic conditions- reactions and mechanisms.
·
Be able to
describe and identify a crown ether including their uses and names)
·
Be able to
understand and interpret the Infrared, Mass Spectroscopy and Nuclear Magnetic
Resonance spectra of ethers.
·
Be able to
identify a thiol and a sulfide.
·
Be familiar with
the synthesis of thiols and sulfides.
· Be familiar with the preparation of sulfoxides and sulfones from sulfides.
VI.
Aldehydes and Ketones: Nucleophilic Addition Reactions (Chap 19)
Students must know or be able to do the following:
·
Define and identify an aldehydes
and a ketones.
·
Be familiar with the industrial preparation of aldehydes
and ketones.
·
Be able to name aldehydes and ketones using the IUPAC rules of nomenclature.
·
Be able to identify the structure and trivial names of common aldehydes and ketones.
·
Know and apply the methods available for the preparation of aldehydes and ketones.
·
Know and apply the oxidation of aldehydes and ketones.
·
Know and apply the nucleophilic addition to aldehydes and ketones-reaction
and mechanism.
·
Be able to discuss and explain the relative reactivity of aldehydes and ketones.
·
Know and apply the nucleophilic addition of
water to aldehydes and ketones
under acidic and basic conditions-reaction and mechanism.
·
Know and apply the nucleophilic addition of
HCN to an aldehyde and ketone-reaction
and mechanism.
·
Know and apply the nucleophilic addition of Grignards to an aldehyde and ketone-reaction and mechanism.
·
Know and apply the nucleophilic addition of
amines to form Imines and Enamines- reaction and
mechanism.
·
Know and apply the Wolff-Kishner Reaction-
reaction and mechanism.
·
Know and apply the nucleophilic addition of
alcohols to aldehydes and ketones
to form acetals- reaction and mechanism.
·
Know and apply the Wittig reaction- reaction
and mechanism.
·
Be familiar with the Cannizzaro reaction.
·
Be able to discuss and apply the conjugate addition reaction of
-unsaturated aldehydes and ketones- reaction and mechanism.
·
Be able to understand and interpret the Infrared, Mass Spectroscopy and
Nuclear Magnetic Resonance spectra of aldehydes and ketones.
VII.
Carboxylic Acids (Chapter 20)
Students must know or be able to do the following:
·
Define and identify
a carboxylic acid.
·
Name carboxylic
acids using the IUPAC rules for nomenclature.
·
Be able to
identify the structure and trivial name of common carboxylic acids.
·
Be familiar with
the structure and physical properties of carboxylic acids.
·
Be able to discuss
the dissociation of carboxylic acids including the impact of substitutents on acidity.
·
Know and be able
to discuss substitutent effects in substituted
benzoic acids.
·
Be familiar with
and able to apply the methods available for the preparation of carboxylic
acids.
·
Be familiar with
and able to apply the reduction of carboxylic acids.
·
Be able to
understand and interpret the Infrared and Nuclear Magnetic Resonance spectra of
carboxylic acids.
VIII.
Carboxylic Acid
Derivatives and
Nucleophilic Acyl Substitution Reactions(Chap 21)
Students
must know or be able to do the following:
·
Define and
identify carboxylic acid derivatives (esters, anhydrides, amides, acid halides,
and nitriles).
·
Name carboxylic
acid derivatives using the IUPAC rules for nomenclature.
·
Be able to
identify the structure and trivial name of common carboxylic acid derivatives.
·
Be able to
discuss and apply the nucleophilic acyl substitution reaction.
·
Know and explain
the relative reactivity of carboxylic acid derivatives.
·
Know and apply
the conversion of carboxylic acids into acid halides, acid anhydrides, and
esters- reactions and mechanisms.
·
Know and apply
the conversion of carboxylic acid halides into carboxylic acids, esters and
amides- reactions and mechanisms.
·
Know and apply
the reduction of acid halides to afford alcohols- reaction and mechanism.
·
Know and apply
the reaction of acid halides with Grignard reagents
to afford alcohols- reaction and mechanism.
·
Know and apply
the reaction of acid halides with organocopper
reagents to afford ketones- reaction and mechanism.
·
Know and apply
the reaction of acid halides with alcohols and amines to afford esters and
amides, respectively- reactions and mechanisms.
·
Know and apply
the conversion of esters into carboxylic acids (acid and basic conditions) and
amide- reactions and mechanisms.
·
Know and apply
the reduction of esters to afford alcohols- reaction and mechanism.
·
Know and apply
the reaction of esters with Grignard reagents to
afford alcohols- reaction and mechanism.
·
Know and apply
the conversion of amides into carboxylic acids (acidic and basic conditions)- reactions and mechanisms.
·
Know and apply
the reduction of amides to afford amines-reaction and mechanism.
·
Know and apply
the methods available for the preparation of nitriles-
reactions and mechanisms.
·
Know and apply
the conversion of nitriles into carboxylic acids
(acidic and basic conditions)- reaction and mechanism.
·
Know and apply
the conversion of nitriles into amines and aldehydes-reactions and mechanisms.
·
Know and apply
the reaction of nitriles with organometallic
reagents to afford ketones- reactions and mechanisms.
·
Have a general
understanding of polymers including polyamides and polyesters.
·
Be able to
understand and interpret the Infrared, Mass Spectroscopy, and Nuclear Magnetic Resonance spectra
of carboxylic derivatives.
IX.
Carbonyl Alpha-Substitution Reactions. (Chapter 22)
Students
must know or be able to do the following:
·
Define and
identify an enol and enolate
and identify the conditions under which they form.
·
Understand and
apply the keto-enol tautomerism
of carbonyl compounds.
·
Explain and apply
the alpha-substitution of enols-reaction and
mechanism.
·
Know and apply
the alpha halogenation reaction of aldehydes and ketones (under
acidic conditions)- reaction and mechanism.
·
Know and apply
the Hell-Volhard-Zelinski reaction- reaction and
mechanism.
·
Predict and
discuss the relative acidity of carbonyl compounds.
·
Know and explain
the reactivity of enolate ions.
·
Know and apply
the halogenation of an enolate-
reaction and mechanism.
·
Know and apply
the alkylation reaction of enolate
ions- reaction and mechanism.
·
Know and apply
the Malonic ester synthesis- reaction and mechanism.
·
Know and apply
the Acetoacetic ester synthesis- recation
and mechanism.
·
Be able to
discuss and apply the direct alkylation of ketones, esters, aldehydes, and nitriles, (including the preparation of lithium diisopropyl diamide).
X.
Carbonyl Condensation Reactions. (Chapter 23)
Students
must know or be able to do the following:
·
Identify an aldol reaction product.
·
Predict the
structure for aldol reaction products
·
Write a mechanism
for an aldol reaction under both acidic and basic
conditions.
·
Know and apply
the dehyrdration reaction of an aldol
product (under both acidic and basic conditions)-
reaction and mechanism.
·
Be able to use
the aldol condensation as a synthetic tool.
·
Identify the
limitations of mixed aldol reactions.
·
Know and apply
the intermolecular aldol reaction- reaction and
mechanism.
·
Know and apply
the Claisen condensation- reaction and mechanism.
·
Identify the
limitations of mixed Claisen condesation
reactions.
·
Know and apply
the intermolecular Claisen condensation (Dieckmann) reaction- reaction and mechanism.
·
Know and apply
the Michael reaction- reaction and mechanism.
·
Identify Michael
"donors" and "acceptors".
·
Be familiar with
the Stork enamine reaction.
·
Know and apply
the Robinson annulation- reaction and mechanism.
· Be familiar with biological condensation reactions.
XI.
Amines (Chapter 24)
Students must know or be able to do the following:
·
Define and
identify an amine.
·
Name amines using
the IUPAC rules for nomenclature.
·
Discuss the
structure, bonding, and physical properties of amines.
·
Discuss the basicity of amines.
·
Know and apply
the methods available for the synthesis of amines including: reduction of nitriles, amides, and nitro compounds.
·
Know and apply
the reductive amination of aldehydes
and ketones- reaction and mechanism.
·
Know and apply
the Hofmann and Curtius rearrangements- reaction and
mechanism.
·
Know and apply
the Gabriel synthesis of amines- reaction and mechanism.
·
Be able to
understand and interpret the Infrared, Mass Spectroscopy and Nuclear Magnetic
Resonance spectra of amines.
Laboratory
(If North Campus obtains the
chemicals and equipment-but most we will not be able to do until the future)
Students who
have completed Organic Chemistry Laboratory I and II (CHEM 2210 and 2211) are
expected to demonstrate the following laboratory skills and abilities.
Students must know and be able to perform
the following procedures:
·
Know and
apply safety rules and regulations pertinent to the organic laboratory.
·
Know the
location and operation of safety equipment in the laboratory.
·
Know and
apply the rules for safe disposal of liquid and solid wastes.
·
Know and
apply the use of balances for massing solids.
·
Know and
apply the use and manipulation of separatory funnels
and conical vials for
extraction purposes.
·
Know and
apply the use of pipets for transferring liquids.
·
Know and
apply the use of anhydrous inorganic salts to dry organic solutions.
·
Be
familiar with the preparation of samples for melting points.
·
Know and
apply the determination and analysis of melting points.
·
Know and
apply the recrystallization procedure for
purification of solids.
·
Know and
apply the use of distillation for the separation / purification of liquids.
·
Be
familiar with the operation and manipulation of a gas chromatograph for the
separation and quantification of organic compounds.
·
Know and
apply the use of column chromatography for the separation of a mixture of
organic compounds.
·
Know and
apply the use of thin layer chromatography for the separation of a mixture of
organic compounds.
·
Be able
to calculate Rf
values.
·
Be
familiar with the operation of a centrifuge for the physical separation of a
solid from a liquid.
·
Know and
apply the use of polarimetry to investigate the
optical purity of a sample.
·
Know and
apply the use of molecular modeling software for the determination of energy
levels of various conformations of organic molecules and the determination of
the lowest energy conformation of an organic molecule.
·
Know and
apply the calculation of theoretical yields and percent yields for a given
experiment.
·
Be
familiar with the theory involved in the use of Infrared Spectroscopy, Mass
Spectroscopy, and Nuclear Magnetic Resonance.
·
Know and
apply the use of Infrared Spectroscopy, Mass Spectroscopy, and Nuclear Magnetic
Resonance spectral data for identification and determination of the structure
of an organic molecule.
·
Know and
apply Excel for the graphing and presentation of spectroscopic data.
·
Be
familiar with the three major classes of biomolecules
and how their structure relates to organic chemistry.
·
Be able
to write a lab report following the American Chemical Society guidelines for
the experiments carried out in lab.
·
Be able
to cite references using ACS standardized format.
·
Keep a
laboratory notebook that contains the appropriate data / information for labs
performed.
·
Be able
to complete worksheets that deal with the experiments performed in the lab.
·
Be able
to carry out synthetic organic reactions that correspond to material covered in
lecture. Be able to collect analytical
data including melting point, boiling point, Infrared spectral data, Nuclear
Magnetic Resonance data, etc. for these reactions. These syntheses may include but are not
limited to any of the following reaction types:
·
Bromination of an alkane
·
Dehydrobromination of
an alkyl halide
·
Free
radical halolgenation of an alkane
·
Nucleophilic substituion
·
Diels Alder reaction
·
Electrophilic
aromatic substitution
·
Reduction
of a ketone with sodium borohydride
·
Oxidation
of an alcohol
·
Wittig reaction
·
Reaction
of a Grignard reagent with CO2
·
Fisher esterification
·
Aldol condensation /
dehydration
·
Preparation
of an alcohol by addition of a Grignard reagent to an
ester
·
Photochemical
reaction
·
Saponification
·
Synthesis
of a heterocycle imine
FCCJ CHM 221C Course
Outline Model:
COURSE TOPICS CONTACT HOURS
__PER
TOPIC__
I.
Organometallic
Compounds 2
A. Structure and
Nomenclature
B. Preparations
C. Reactions and
Properties
D. Uses
II.
Aldehydes
and Ketones 6
A. Structure and
Nomenclature
B. Preparations
C. Reactions and
Properties
D. Uses
III.
Carboxyllic
Acids 4
A. Structure and
Nomenclature
B. Preparations
C. Reactions and
Properties
D. Uses
IV.
Carboxyllic
Acid Derivatives 5
A. Structure and
Nomenclature
B. Preparations
C. Reactions and
Properties
D. Uses
V.
Enolate
Anions and Similar Structures 6
A. Aldol
Reaction
B. Claisen
& Dieckmann reactions
C. Micheal
additions
D. Related synthetic
applications
VI.
The Structure of Aromatic
Compounds 4
A. Nomencalture
B. Structure
C. Spectroscopic
properties
VII. Aromatic
Compounds 6
A. Electrophillic
Aromatic Substitution
B. Substituent
Effects
C. Nucleophillic
Aromatic Substitution
D. Related synthetic applications
VIII. Amines 4
A. Structure and
Nomenclature
B. Preparations
C. Reactions and
Properties
D. Uses
IX.
Conjugated Systems 4
A. Structure
B. Spectroscopic
properties
C. The Diels
Alder Reaction
D. Pericyclic
reactions, The Claisen and Cope Rearrangements
E. Related synthetic applications
X. Special
Topics 4
Our Learning Community:
Quiz monitors,
attendance monitor, personal assistants, test preparers, camera
persons/editors, study guide word processor assistant, Chemistry WebMasters, as well as study groups are forms of
cooperative learning environments where the student needs to learn how to
function in teams. Each
student MUST take charge of his/her commitment to learning in order to achieve
success in not only this course but also in college.
Power Points from the 6th
edition of the textbook may be found at:
http://www.fccj.us/cham2210/PowerPoint/2210pptmenu.html
The 6th edition Student Companion Web Site:
On the web
site are sample chapter multiple choice exams and more questions label Organic
interactive. Student are expected to complete both for each of the chapters
Grading Scale:
|
Overall Percentages |
Grade |
|
100 – 90 % |
A* |
|
89 – 80 % |
B* |
|
79 – 65 % |
C* |
|
64 – 50 % |
D* |
|
< 50 % |
F |
*Lab is an essential part of this class. If you acquire less than 60% in lab, you will
automatically receive a letter grade of ‘F’ in this course. If you make less
than 70% in lab you may not earn a grade above ‘D’
Grade Review:
See Grading Sheet (distributed separately) for a point by point summary
of the course. It also serves as a Course outline, indicating sections of the
text being covered on each exam.
Grading
Outline: http://www.fccj.us/chm2211/2211grdF08.htm
Tentative Point Grade Summary:
______ (030) Attendance
_______(820) Chapter
Exams/eLearning (Chapters 10-24)
_______(150) Lab
Assignments [12x10]
_______(1000) Grand Total
Tentative (point)
Instructor’s Right to Change or Modify Grading Procedures:
This instructor reserves the right to make changes in
this syllabus whenever he feels it is appropriate to do so. The instructor
reserves the right to modify or change the grading progress as the course
proceeds. Any additional course assignments will substitute for deleted
items. Some may also be modified if not
deleted. The instructor will not add
major examinations as a modification and maintain the above general category
point distributions.
Other
Pertinent Information (Supplemental Notes):
Students with Disabilities: Qualified students with documented disabilities are eligible for
physical and academic accommodations under the American Disabilities Act and
Section 504 of the Rehabilitation Act of 1973.
Students requesting accommodations should contact Student Development
Services at 264-7220 (voice) or 264-3371 (TTY) and this professor during the first week of class.
Withdrawal Policy:
Students will be allowed to withdraw from this class any time during the
semester through Monday, November 3 for an A-16 schedule and will receive a grade of “W”.
Students failing to attend class for the first two consecutive weeks are
subject to withdrawal by the instructor according to FCCJ policy. These ‘no shows’ must be reported to
Admissions and Records by the end of two weeks Tuesday January 22
Academic Misconduct:
Academic misconduct or dishonesty such as cheating and plagiarism is not permitted. Suspected cases will be reported to the Dean of Liberal Arts and may result in failure of an assignment or exclusion from the class. Also, the instructor reserves the right to reassign work to students if the instructor senses the work submitted is not the work of the student. (No questions asked-The instructor may tell the student to resubmit the work to earn the daily quiz grade or examination grade or may sign a zero if second request is made).
Classroom Etiquette:
Students are expected to conduct themselves as
adults in the classroom showing respect to their classmates. Only persons
registered for this class are permitted in the laboratory. As a courtesy to the instructor and your
fellow classmates, cellular
telephones and pagers should be cut off before entering the classroom or
laboratory. Likewise, the instructor sometimes forgets to shut his down
at the beginning of class, so hopefully someone sitting close to the front may
remind the instructor with a hand gesture for him to check his phone,
Children in the Classroom
Policy: It is the goal of FCCJ to provide a safe and
effective learning environment for all students. Any action, which interferes with this goal,
will not be permitted. Children must not
be left unattended at any time on campus.
If an emergency arises which requires a student to bring an underage
child (defined as any child under the
age of sixteen who is not a FCCJ student enrolled in a credit class) to campus,
the child must be under the direct supervision of an adult at all times. Parents and guardians of children considered
disruptive or unsupervised will be asked to remove the children from the campus
immediately.
Bringing children to the classroom is not
permissible under most circumstances.
However, if an emergency arises which necessitates bringing a child to class, the student must receive the prior consent of the
faculty member involved. Children who
are ill may not be brought to class regardless of the circumstances. Due to the nature of the equipment, the
subject matter involved, and the level of supervision necessary, underage
children will not be allowed in college laboratories or in the
Children enrolled in non-credit classes must be under the direct supervision of an adult at all times. Likewise, children attending campus events must be supervised at all times. Any child under the age of 16 must be under the direct supervision of his/her parent, legal guardian, or other responsible adult when in the college library unless the child is part of a call AND the supervising teacher or paraprofessional is present
Studying: In order to do well in this course, it is
essential to study and work problems.
The following is a list of study suggestions
1)
Read the text chapters before the material is covered in class.
2)
Take good notes and review them daily.
3)
Work all assigned homework problems.
Do not get behind!!!!!!
4)
Work the practice exams that will be made available without looking
at the answer key.
5)
Work problems in ACS study guide.
6)
Use the interactive CD-Rom for studying.
‘Muddy
Water’ Issues:
Each day, students may use 3x5 file cards
(as provided by the instructor the first week) to list the day’s muddiest water
issue or send the instructor an email immediately after class. What was confusing? What don’t you understand? What problems at the end of the chapter
overwhelm you? As you leave the
classroom, you will submit a card with your name and the issue or issues. If you are absolutely on target, no problem
then no card submitted a card indicates to the instructor you are on course on
time and understand the learning concepts. At the end of each on-line
group/individual quiz/homework may be a place to journal your discovery
statements, the muddy water issues, and check list of vocabulary words that you
do not understand.
The
(904) 766-6718
The
The Center is open Mon-Thur 8 a.m.-10:00 p.m. Friday and Saturday 8:00 a.m.-3:00 p.m.
The
Additional
Chemistry Web Sites:
Chemdex is a large chemistry directory created by Dr. Mark
Winter at the Department of Chemistry,
Links
for chemists and Virtual Library chemistry may be found at:
http://www.liv.ac.uk/chemistry/links
Chemistry
Web Guide: http://science.searchbeat.com/chemistry.htm
Galaxy:
Chemistry: http://wwww.galaxy.com/galaxy/Science/Chemistry.html
The
NIST Chemistry WebBook (database of physical data and
spectra):
Online Multiple
Choice:
The student
will complete the online multiple choice for the text book and send the results
to the instructor for up to 20 points per chapter. The student must completely
fill-in the blanks with names and both emails to receive credit:
Brooks-Cole McMurray 6th
Edition Web Quiz
Assignment Name: Chapter 10:
Alkyl Halides
|
Summary of Results
|
||||||||||||||||
To email the results to your instructor(s),
complete this form:
Required field
|
||||||||||||||||
Web
Link:
Instructor
Requested Information:
During the
first week of class, the student will fill out a 4x6 file card. The instructor
has provided a sample below with his personal data and his block scheduled
time. The completion of this card is worth
(2 points)
toward the student's final grade
Data Card (4x6 file
card): Front Side (Personal Data)
--------------------------------------------------------------------------------------
Name: John Taylor CHM 22110C
Office: D-270
Address:
Telephone: 904-766-6763
(office)
Cell: 904-614-0531 Home:
904-992-2052
E-MAIL : johtaylo@fccj.edu
Employment: FCCJ since 8/21/06
Full time chemistry faculty
Major:
Instructional Technologies Minor:
Chemical Education
Long Term
Goal: Educational Software Developer
Prerequisite: MAC
1105 equivalent Algebra completed: yes
Chemistry
Background: CHM 2046C: yes A
Physics
Background: High School Physics completed: no
Software/Computer
Literacy: WP, Word, Excel, HTML, Javascript
Home Computer: yes Internet ISP: yes or have access
Why are you
taking this course? Required for chemistry major
--------------------------------------------------------------------------------------
Data Card (4x6 file card):
Back Side (Scheduled Time Blocks)
Class/Work Schedule Summary:
Number Section Room Time Days
CHM 1020 283919 A-171 3:00-4:15 p.m.
MW
CHM
1025C 286714 D-207 9:00-12:00 p.m. R
Lab
D-204 9:00-12:00 p.m. T
ESC 1000 270079 D-207 12:00-1:15 p.m. MW
CHM 2046C 284690 D-207 1:00-4:00 p.m. R
Lab
D-204 1:00-4:00 p.m. T
CHM 2211C 286138 D-207 7:00-10:00 p.m. M
Lab D-204 7:00-10:00 p.m. W
Class/Office Matrix Schedule (Where is Your
Instructor?):
My Schedule Matrix: I have 10
hours of office hours, Office/Pretest
means I am in the course’s classroom, while Office means my office D-270.
You must find 10 hours in you weekly matrix for studying chemistry. Please make
your own!
|
Time |
Monday |
Tuesday |
Wednesday |
Thursday |
Friday |
|
7:30 |
|
At Home |
|
At Home |
|
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8:00 |
At Home |
On the Road |
At Home |
On the Road |
Community |
|
8:45 |
Course |
On the Road |
Course |
On the Road |
Service |
|
9:00 |
Preptime |
CHM 1025C |
Preptime |
CHM 1025C |
Projects |
|
9:30 |
Preptime |
Lecture 9-10 D-TBA |
Preptime |
Lecture 9-12 |
Off Campus or |
|
10:00 |
Preptime |
Lab 10-12 |
Preptime |
D207 |
Corporate |
|
10:30 |
On the Road |
D-204 |
On the Road |
Lecture |
Computer |
|
11:00 |
On the Road |
Lab |
On the Road |
D207 |
Training |
|
11:30 |
Pretest/Office A0171 |
Lab |
Pretest/Office A0171 |
Lecture |
Off Campus or |
|
12:00 |
ESC 1000 |
Office/Pretest D204/D270 |
ESC 1000 |
Office/Pretest D207/D270 |
Special |
|
12:30 |
A0171 Earth Science |
Office/Pretest D211 |
A-171 Earth Science |
Office/Pretest D211 |
Help |
|
1:00 |
Sect# 283919 |
CHM 2046C |
Sect# 283919 |
CHM 2046C |
Pre-testing |
|
1:15 |
Pretest/Office A-171 |
Lecture D-211 |
Pretest/Office A0171 |
Lecture D-211/204 |
Sessions |
|
1:30 |
Office: D-270 |
Sect# 284690 |
Office: D-270 |
Sect# 284690 |
as |
|
2:00 |
Office D-270 |
CHM 2046C |
Office D-270 |
CHM 2046C |
announced |
|
2:30 |
Office/Pretest A-171 |
CHM 2046C |
Office/Pretest A-171 |
Lab D 204 |
via |
|
3:00 |
CHM 1020 |
Lecture |
CHM 1020 |
CHM 2046C |
email |
|
3:30 |
Lecture A-171 |
D-211 |
Lecture A-171 |
Lab |
On Campus |
|
4:00 |
Sect#283919 |
Office/Pretest D-211 |
Sect#283919 |
Office/Pretest D-211/204 |
|
|
4:15 |
Office/Pretest A-171 |
Office D-270 |
Office/Pretest A-171 |
Office D-270 |
|
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4:30 |
|
On the Road |
|
On the Road |
|
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5:30 |
|
On the Road |
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On the Road |
|
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6:00 |
2211 Pretesting |
|
2211 Pretesting |
|
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6:30 |
Pretesting
D-203A |
CHM 2046C |
Pretesting
D203A |
CHM 2046C |
|
|
7:00 |
CHM 2211C |
Independent Study |
CHM 2211C |
Independent Study |
|
|
7:15 |
Sect#286138 |
See Above |
Lecture |
See Above |
|
|
7:30 |
D-207 |
|
Sect#286138 |
|
|
|
8:00 |
CHM 2210C |
|
Lab/Lecture |
|
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8:30 |
Lecture |
|
Lab Room |
|
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9:00 |
D-207 |
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D-204 |
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9:30 |
Lecture |
|
Lab |
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10:00 |
Office D-270 |
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Office D-270 |
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10:15 |
On the Road |
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On the Road |
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10:30 |
On the Road |
|
On the Road |
|
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Student’s Class/Work Matrix Schedule:
Where can you find 10 hours per week minimum to study?
Name:
___________________________ CHM 2046C Fall Term 2008
|
Time |
Monday |
Tuesday |
Wednesday |
Thursday |
Friday |
Saturday |
Sunday |
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7:30 |
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8:00 |
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Submit this form the second class period