Organic Chemistry II

CHEM 242 - Section 1 Fall 2014

Class Time:
Section 1:

Monday and Wednesday 8:10 - 10:00 AM

Class Room:

H-2

Instructor Name: Dr. D. T. Whitaker

Office Location: S-16F
Phone Number: (313) 845-9724
Instructor e-mail: whitaker@hfcc.edu
Course e-mail: dtwchm242@gmail.com
Office Hours:

Mon, Wed 10:00 11:30 am; 1:30 4:30 pm

Tue 12:10 1:00 pm

MoodleRooms: 1) go to www.hfcc.edu
2) click on MoodleRooms
3) MoodleRooms login is the same as Webadvisor

Course Description, Materials, and Policies

Course:
CHEM 242 (Organic Chemistry II)
Prerequisite:
Chem 241 with a grade of C or better.
Course Description:
A continuation of Chemistry 241 with emphasis on acid-base chemistry, spectroscopy, and retrosynthetic analysis.
Reaction mechanisms and physical properties of the following functional groups will be explored: carbonyl chemistry
(aldehydes, ketones, and carboxylic acid derivatives); carboxylic acids; amines; carbohydrates; lipids; amino acids,
proteins; and nucleotides. This course should meet the requirements for science majors and premedical, pre-dental,
pre-pharmacy, and chemical engineering students. Four hours of lecture per week without lab.

There is no text for this course. Extensive use of lecture materials at MoodleRooms will
be employed.
Required:

On-line access for the Online Web-Based Learning (OWL) website

(http://owl.cengage.com/)

IMPORTANT NOTE: When you register for OWL, register for the
following text (DO NOT BUY THE TEXT): W. H. Brown, C. S. Foote, B. L. Iverson,
E. V. Anslyn Organic Chemistry, 5th Ed. New York: Brooks/Cole, 2009. Do NOT register for the
enhanced edition.
You may use the same OWL from Chem 241 if you took it here. Otherwise follow these
instructions for purchasing OWL online:
1) go to http://owl.cengage.com/
2) slide down the Organic Chemistry menu to Buy an access code
3) choose the following book: Organic Chemistry, 5th Edition Brown, Foote,
4)
5)
6)
7)

Iverson, Anslyn.
choose your option (do NOT buy the eBook), 6 months or 24 months
checkout and pay
OWL will send you an access code with instructions for installing OWL access
When you register for the course you should register for the book indicated in line
3 at Henry Ford Community College

OWL Resources:
Students are provided with quick start guides for using the MarvinSketch drawing
tool, and getting started using OWL at: http://owl.cengage.com/ . Students should
go to this site during the first week to familiarize themselves with OWL.
Suggested resource:
The following website from Michigan State University provides useful practice
problems which serve to supplement those found at MoodleRooms and the practice
exams:

http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/Questions/probl
ems.htm
Required e-mail:
Students should use their HFCC e-mails for all course correspondence. You can get to your
HFCC e-mail account by going to www.hfcc.edu Then click on current students and the
Groupwise web access. Please DO NOT use the MoodleRooms e-mail for

correspondence! Use my Gmail e-mail or hfcc.edu address (above). Use YOUR HFCC
Groupwise Novell e-mail address or establish a new e-mail address for this course. Have
your username for your new e-mail match as closely as possible to your MoodleRooms
username.
Logging onto School Computers:
Your tuition has given you access to the school computers. Check the media center schedule
and login procedures at www.hfcc.edu
Course Objectives

Students who successfully complete the assignments of this course should be

able to:
1.
Demonstrate various levels of proficiency with predicting the mechanisms
of reactions of various classes of organic molecules including, but not limited to
ethers, aldehydes, ketones, carboxylic acids, carboxylic acid derivatives (acid
halides, anhydrides, esters, amides, nitriles), other acid derivatives
(sulfonamides, imides, phosphoric anhydrides and esters, chromic anhydrides),
amines, aromatics and other conjugated systems.
2.
*Demonstrate the use of critical thinking skills in the analysis of chemical
reactions.
3.
Recognize and give examples of the importance of searching for patterns
when one is studying the sciences and carrying out investigations and/or
experiments.
4.
Demonstrate the ability to name complicated organic and biochemical
molecules.
5.
Be able to devise a synthesis for relatively elaborate organic compounds
(using retrosynthetic analysis).*
6.
Demonstrate the ability to predict the physical properties of molecules
based on an understanding of functional groups.
7.
Demonstrate the ability to predict reactions between molecules base on
an understanding of functional groups and bonding.
8.
Describe how chemical reactions mediate biological processes.
9.
Demonstrate competence with identification of functional groups and
organic reactions of biomolecules.
10.
Demonstrate familiarity with traditional library resources and electronic
media and use criteria with which to judge the reliability of various resources.
11.
Demonstrate proficiency with communication using e-mail.
12.
Demonstrate proficiency with course management software such as
Blackboard or UCompass.
13.
Demonstrate the ability to function in a team setting.

Policies
Attendance:

This is a subject where attendance takes care of itself. Organic

Chemistry is a course that continually builds on itself. If you dont understand the
material from todays lecture then you are pretty much wasting your own time trying
to understand tomorrows. If you fall behind in lecture or in studying, you are
almost certainly going to do poorly. It is also my personal experience that only
exceptionally gifted students can miss more than 10% of the lectures and still
receive a good grade in this class. So, attendance will not be counted as a grade
per se, but it will strongly affect how well you do at the end of the semester.

Attendance: Students are expected to attend every lecture session, for the full, allotted
time. Students who have conflicts that preclude regular, prompt, and complete
attendance should not register for the class.
NA Policy: Henry Ford College requires students to actively participate in their learning
with regular and sustained interaction. Since student success depends on active
engagement, students who have NOT attended an entire class session by the College's
Never Attended deadline will not be permitted into the class even if they are already
enrolled in the class. Online students will be considered as "Never Attended" if they
have not logged on or if they have only logged on without actively engaging in
academically-related activities. All of the above students will be assigned a "Never
Attended" grade on their record. September 10 is the Never Attended deadline record
day for the fall 2014 term.
DROP POLICY:
1. A student may withdraw from a class during the first week (for full refund).
2. A student may initiate a drop/withdraw at the registrars office. Nov 5 is the last day to
drop fall 2014 semester classes. The grade W will appear on the transcript.
3. At the instructor discretion the instructor may submit a grade of DR at the end of
the semester to any student who specifically asks for a drop and who does not take the
final exam.
4. Students who drop the course in the registrar's office on or before the official drop
date are automatically assigned a grade of W.
We recommend that students remaining in the class after the official drop date
receive a letter grade.

Missed Lecture Policy:

Organic Chemistry is a subject that keeps building on the knowledge of the previous lecture.
Missing lecture is a very bad idea. In order to ensure that no students fall behind, I am
strongly suggesting that each student who has to miss a lecture for any reason should try to
do the following:
1) Get notes from the missed lecture from a fellow classmate. Further notes may be found at

MoodleRooms for most lectures.

2) Write out the notes by hand (yes, YOUR hand, BOTH IN-CLASS NOTES AND
MOODLEROOMS NOTES).
3) Bring the notes to class the next time the class meets and show them to the instructor.
IT IS A GOOD IDEA TO ESTABLISH AT LEAST TWO CONTACT PEOPLE IN THE CLASS.
DO NOT BE SHY, IT IS A GOOD IDEA TO ESTABLISH STUDY GROUPS EARLY IN THE
SEMESTER.

Special Needs:
If a student has any special needs please inform the instructor EARLY in the semester.

Assessment:
Assessment boils down to asking yourself this simple question: Am I learning what I should be
learning in this class? In order to assess your answer to this question, we will be doing several
things this semester. The on-line web-based learning (OWL) portion of this course is an ideal
way to receive prompt feedback to help you answer that question. Students taking this course
are expected to have a high enough level of maturity to evaluate their progress by attempting
the texts homework problems and evaluating their understanding by means of the Solutions
Manual. Substantial use of Homework problems on tests will also reward those doing the
homework.

Office Hours:
Office hours are listed at the top of each syllabus item. I take office hours very seriously and
expect students to take advantage of them whenever they need extra help with the course
material. Consult your e-mail for any changes to office hours. Also, feel free to direct questions
anytime either by e-mail or phone.

Cheating: What is cheating? For one, it is something I hate. Presenting someone elses
thoughts as your own is a reasonable description of cheating. Ultimately, you are
cheating yourself if you try to pass off someone elses work as your own. This
WILL catch up with you. Maybe in this class, maybe later. Maybe with a grade of
zero now, maybe the loss of your job later, or worst, the death of another (others)
caused because you didnt understand what you were copying. My policy is
simple.

HERE IS WHAT WILL HAPPEN IF YOU ARE CAUGHT CHEATING IN

THIS CLASS:
1) I will immediately submit a grade of E to the registrar for this class.
2) I will write a detailed report of the cheating incident and give you a copy. This
detailed report will clearly state that you received a grade of E for this class
BECAUSE YOU CHEATED.
3) I will submit a copy of this report to the Registrar. The registrar will create a file
for you.
NOTE: If you received two (2) Es for different courses at HFCC as a result of
cheating, you will be expelled from the school.
For a more detailed discussion see the syllabus item titled
PolicyOnAcademicDishonesty.

Missed Exams:
There are no makeup exams in this class. You must inform Dr. Whitaker
that you are going to be absent from an exam BEFORE THE

EXAMINATION BEGINS.

You must do this either by voice mail at

(313) 845-9724 or by e-mail at whitaker@hfcc.edu. If you do not have your
syllabus with you and you have forgotten both the phone number and e-mail
addresses then you are to phone the main HFCC switchboard (directory
assistance will take you there) and have them dial up Dr. Whitakers extension for
you. There are no exceptions to this policy. You must provide adequate
documentation as to the reason for your absence. A doctors note must state that,
in the opinion of the doctor, you were unable to take an exam due to your
condition. Documentation must also be provided for any other reason an exam
may be missed. It is up to the discretion of the instructor as to what a valid excuse
is for a missed exam. In other words a medical checkup is not a valid excuse. If
you have any scheduled appointments for an exam day then please change that
appointment ASAP. The exam dates (page previous) are final. The material on
the exams may be less than or more than indicated. Failure to satisfactorily
comply with this missed exam policy will result in a grade of zero (0/100) on
the missed exam. This zero WILL NOT BE DROPPED (the zero will be
averaged with all of your other test scores to compute your test average).
Death in the family: I know that death in the family is an emotionally difficult time.
If you must miss an exam due to the death of a family member you have to provide
adequate documentation to show me that there was indeed a death in the family
(example, a photocopy of the death certificate or a receipt from a funeral home). I
have had to add this new item because it has come to my attention that students
have lied in the past to me about this matter.

Drop Policy:
Students can drop the class on their own at Webadvisor or at the Registrars office
throughout the first five weeks of class
(See: http://www.hfcc.edu/programs/class_schedule.asp for exact dates). The
instructor will submit a drop at the end of the semester for any student who
requests a drop BEFORE THE FINAL LECTURE. The instructor will not give a
drop after the student has taken the final exam.

Incomplete Policy:
An incomplete is only granted to students who have been successfully keeping up
with the coursework (a grade of C or better) up to a point where a personal
tragedy occurs in their life and they are unable to finish the course work. This must
be discussed with the instructor on a case-by-case basis.

Classroom Behavior and Safety:

Organic Chemistry is a very challenging subject. Nothing, as a teacher, makes me
happier than seeing students work hard and succeed at this subject. In the
classroom it is my responsibility to provide an environment that is as conducive to
your learning experience as possible. Towards that end I have these
guidelines that I would like everyone to follow. I too will try my best to follow
these guidelines.
1) Treat others the way that you want to be treated.
2) Treat people equally and impartially

3) Consider the feelings of all people who will be affected by your

actions.
4) Be open-minded and responsible.
5) Play by the rules.
6) Do not take advantage of others.
7) Do not be disruptive.
8) ENTERING CLASS LATE: Do not come to class late on a regular
basis. If you must enter the room late, please do so quietly from the
rear door. Do not talk to fellow students when you come in late.
WARNING: If you are late for class more than 7 times the teacher
reserves the right to deduct points from your grade. If you tried to do this
while you were working, you would eventually be fired.
9) There is a phone down the hall near the elevator. The number for
Campus Safety is 9-911. If there is an incident where the safety of
you or your fellow students is in jeopardy while the teacher is not in
class, do not hesitate to phone this number.
10) During fire alarms, please exit the room in an orderly, courteous
fashion. If the all-clear signal is given while there is still at least 20
minutes left in the class period, you are expected to return to the
classroom.
11) Cell phones are not permitted to be used in the classroom. DURING
EXAMS YOUR CELL PHONE MUST NOT BE VISIBLE TO THE
INSTRUCTOR. IF A CELL PHONE IS SEEN DURING AN
EXAMINATION IT WILL BE CONFISCATED BY THE INSTRUCTOR
AND RETURNED AFTER THE EXAM HAS BEEN TURNED IN.
Children:
Please do not bring children into the classroom. I am unable to devote my total attention to
teaching when children are around because I want to pay attention to them. Please try to work
out a backup daycare plan in case your primary daycare needs fall through during the semester.
Teacher has not made it to lecture by the start of class time:
I very rarely miss the start of lecture time. If an emergency prevents me from being there at the
start of class time, I will make every effort to inform another faculty member who will post a note
outside the lecture room. Please DO NOT assume class has been cancelled until at least 20
minutes after the start of lecture time. I request that a student goes to my office (S-13) before
the 20 minutes are up to verify that the I am NOT on campus already.

Recording of lectures.
Students are permitted to record (sound only, NO VIDEO) lectures. If a student wishes
to record a lecture they must announce it to the class by writing "This lecture is being
recorded" on the top right corner of the whiteboard using a dry-erase marker. Video
recordings will not be permitted under any circumstances.
Cellular Phones.
Students are NOT permitted to use cell phones in the classroom. Cell phones must
either be turned off or set to vibrate only. If the instructor sees a cell phone in the
classroom it will be confiscated from the student and returned at the end of class. If you
7

have an emergency need to use a cell phone during lecture, tell the instructor and they
will keep the cell phone at the front of the class and warn you as necessary if it vibrates.
Major Core Course Objectives (Measurable):
Students who successfully complete the assignments of this course should be able to:
Demonstrate various levels of proficiency with predicting the mechanisms of reactions
of various classes of organic molecules including, but not limited to alkynes,
ethers, aldehydes, ketones, carboxylic acids, carboxylic acid derivatives (acid
halides, anhydrides, esters, amides, nitriles), other acid derivatives (sulfonamides,
imides, phosphoric anhydrides, chromic anhydrides), amines, aromatics and other
conjugated systems.
Demonstrate the use of critical thinking skills in the analysis of chemical reactions.
Recognize and give examples of the importance of searching for patterns when one is
studying the sciences and carrying out investigations and/or experiments.
Demonstrate the ability to name simple and somewhat complicated organic and
biochemical molecules.
Demonstrate the ability to predict the physical properties of molecules based on an
understanding of functional groups.
Demonstrate the ability to predict reactions between molecules base on an
understanding of functional groups and bonding.
Describe how chemical reactions mediate biological processes.
Demonstrate competence with identification of functional groups and organic reactions
of biomolecules.
Demonstrate familiarity with traditional library resources and electronic media and use
criteria with which to judge the reliability of various resources.
Demonstrate proficiency with communication using e-mail.
Demonstrate proficiency with course management software such as Blackboard,
uCompass, or MoodleRooms.
Demonstrate the ability to function in a team setting.
Display professional behavior, courtesy, and attitude.

Test Dates and Grading Policy

The final exam is not during normal class hours:
7:55 - 9:40 AM
ALL EXAMS WILL BE GIVEN IN THE BERRY AMPHITHEATER IN THE
ASCC BUILDING (AS-115)
Exam #
1
2
3
4
Final

Date

Chapters

Monday October 6
Wednesday October 29
Monday November 17
Monday December 8
Wednesday December 17

Review, 13, 15, 16

17, 18, 19
21, 22, 23, 25 (partial)
25, 26, 27
Cumulative (Organic Chemistry)

Test Dates are FIXED. Material may vary.

Overall Grade Breakdown

Tests
Online Web-Based Learning
(OWL)
In class presentation

16.7% each

45%

See OWL website

10%

You schedule

5%

Reaction Mechanism Journal Due before each exam

(starting with exam #2)
Final Exam Cumulative (50% Multiple

5%
35%

Choice, 50% Mechanisms)

Grading Scale: (read very carefully below).

A* 90 - 100% B** 80 89%
C*** 60 79%

D 50 59%

E <50%

Average is not the only criteria. You must satisfy ALL of the conditions below in
order to obtain the grade indicated above.
*To receive an A in this class, you must:
1. Have an overall average of over 90%.
2. Have at least 90% on two tests.
3. Receive no less than 80% on the final exam.
Exceptional performances will be rewarded with an A+. So, what is an exceptional
performance?
1) Over 95% on each exam (Exam #s 1 4 AND Final).
2) Over 95% on OWL.
9

3) Over 95% on the Reaction Journal.

The HM amendment (Fall 2006):
Alternatively, an A+ will be granted if a student receives 100% on three of the four
exams AND the final, while ALSO receiving 100% on OWL AND the reaction Journal.
**To receive a B in this class, you must:
1. Have an overall average of at least 80%.
2. Have at least 80% on two tests.
3. Receive no less than 70% on the final exam.
***To receive a C in this class, you must:
1. Have an overall average of over 60%.
2. Have at least 60% on two tests.
3. Receive no less than 50% on the final exam.
CCAP Testing:
Henry Ford College (HFC) will be using the Collegiate Assessment of Academic Proficiency Test
(CCAP), which is used at colleges and universities nationwide, to determine if HFC students
are mastering the Colleges general education outcomes. General Education outcomes
represent the basic skills each graduate should have upon graduation. As a result, this course
section may be randomly selected from among the hundreds of classes at HFC. The test will
take approximately sixty (60) minutes in one of your class meetings if your section is
randomly selected. The assessment test administered in your class will be in one of the
following areas: Computer Literacy, Reading, Writing Skills, Mathematics, Essay Writing, or
Critical Thinking. This test is NOT RELATED to your current course and will have no effect on
your grade. The College will use the test results to improve teaching and learning.
The date for this test will be Monday October 27

What is the classroom presentation?

As the semester proceeds you should try to find an area of organic chemistry that
interests you. This could be a new medicine, class of medicines, a poison that hits the
news, or anything else that you find relevant. You should talk about the structure of the
molecule and the rest is up to you. It should be a 10 minute talk. You can use any
media available in the classroom (Powerpoint, ELMO, etc). You must submit a onepage summary of your talking points at least a day before your presentation. This
summary must include your references. The instructor will photocopy the summary for
the whole class.
Student Motivator:
How should I approach Chemistry 242?
The main goal of this course is to prepare you for success in Chemistry 242. After
Chemistry 242 you will be ready to understand how molecules interact, are assembled,
and are broken down both in the lab and in living organisms. This is of critical
10

importance to all who hope to enter into any health related careers (examples:
pharmacy, medicine, dentistry, nursing, etc.). SO LEARN THE MATERIAL AS IF YOU
WILL NEED IT FOR for 10 EXAMS 8 semester exams + final for both 241 and 242.
Then try to keep this knowledge as you move on to other classes such as Biochemistry
and Molecular Biology.

This is a quote from an advertisement for one of our college's fine radio shows
(WHFR, 89.3 FM, Fridays 6-8 PM, Space Is the Place).
"Warning, this show may impose cerebral responsibility on the listener."
This is a new item for the course's syllabus.
"Warning, this course will impose cerebral responsibility on the student."

Good Luck in Organic I, dtw

11

Mechanism Journal And On-Line Web-based Learning (OWL)

Mechanisms
Chapter

Sect.
Version 4
11.4A
11.4C
11.5A
11.8B
MoodleRooms
11.8C
11.9A
11.9B

Sect.
Version 5
11.4A
11.4C
11.5A
11.8C
MoodleRooms 11.8B
11.9A
11.9B

15

15.1B
15.1C
15.3B

15.1B
15.1C
15.3 B

16

16.6A/B
16.6C
16.6D
16.7
16.8B
16.9
16.10A
MoodleRooms
16.11A
16.12C
16.12C
16.14B
MoodleRooms

16.5A/B
16.5C
16.5D
16.6
16.8B
16.9
16.8A
MoodleRooms
16.9A
16.12C
16.12C
16.11A
16.11A

17

17.6A/MoodleRooms
17.7B
17.7C
17.8
17.9A/B

17.6A/MoodleRooms
17.7B
17.7C
17.8
17.9A/B

11

12

Topic
Williamson ether synthesis
Acid-catalyzed addition of alcohols to alkenes
(formation of ethers)
Acidic cleavage of an ether with HCl, HBr, or HI
Epoxidation of alkenes using RCO3H
Acid catalyzed hydrolysis of ethers using
water/sulfuric acid
Halohydrin formation (see 6. 3E) / Internal SN2
Acid-catalyzed opening of epoxides
Nucleophilic opening of epoxides
Acid-base reactions of Grignard Reagents and
Organolithium reagents
Reactions of Grignard Reagents and Organolithium
reagents with epoxides
Formation of dichlorocarbene and reaction with
alkenes
Grignard/Organolithium addition to aldehydes and
ketones.
Addition of terminal alkyne anions to aldehydes and
ketones.
Formation of a cyanohydrin.
Phosphonium ylide formation / Wittig reaction.
Acid catalyzed formation of hemiacetals and
acetals.
Reactions of 1,3-dithiane anions with electrophiles.
Imine formation from aldehydes and ketones.
Enamine formation from aldehydes and ketones.
Keto/Enol tautomerization.
Acid-Catalyzed a-halogenation of a ketone.
Base-Catalyzed a-halogenation of a ketone.
NaBH4 reduction of aldehydes and ketones.
Wolff-Kishner Reduction
Reduction of Carboxylic acids using lithium
aluminum hydride (MoodleRooms)
Fischer esterification.
Formation of methyl esters using diazomethane
(CH2N2).
Reaction of carboxylic acids with SOCl2
Decarboxylation of -carbonyl containing carboxylic
acids.

18

18.3
18.4B-E
18.4B-E
18.5 A-C
18.6A
18.7
18.9 A-B
18.9 C
18.10 A
18.10 A
18.10 B
18.10 C
MoodleRooms

18.3
18.4B-E
18.4B-E
18.5 A-C
18.6A
18.7
18.9 A-B
18.9 C
18.10 A
18.10 A
18.10 B
18.10 C
MoodleRooms

19

19.2
19.2
19.3A-C
19.5A-B
MoodleRooms
19.8A
MoodleRooms

19.2
19.2
19.3A-C
19.5A-B
MoodleRooms
19.8A
MoodleRooms

21

21.4
21.4E
21.5

21.4
21.4E
21.5

22

22.1

22.1

Nucleophilic acyl substitution.

Acid-catalyzed hydrolysis of carboxylic acid
derivatives.
Base-catalyzed hydrolysis of carboxylic acid
derivatives.
Reaction of carboxylic acid derivatives with alcohols
to give esters
Reaction of acid halides with amines to give
amides.
Reaction of acid halides with carboxylate ions to
give anhydrides.
Reactions of esters with Grignard reagents or
Organolithium reagents
Reactions of acid-halides with Gilman reagents to
give ketones
Reactions of Esters with lithium aluminum hydride
to give alcohols
Reactions of Esters with DIBAL-H to give aldehydes
Reactions of amides with lithium aluminum hydride
to give amines
Reactions of nitriles with lithium aluminum hydride
to give amines
The Hofmann rearrangement of primary amides.
Base-catalyzed aldol reactions/Base-catalyzed
dehydrations.
Acid-catalyzed aldol reactions/Acid-catalyzed
dehydrations.
Claisen condensation (intermol) is the same as the
Dieckmann condensation (intramol)
Alkylation and acylation of enamines.
Hydrolysis of alkylated/acylated enamine products
Michael reaction: Conjugate addition (1,4) of
stabilized enolate anions.
Robinson Annulation (MoodleRooms)
Phenoxide resonance
Kolbe synthesis: carboxylation of phenol towards
the pharmaceutical synthesis of aspirin.
Benzylic Resonance
Electrophilic aromatic substitution:
Chlorination/Bromination; Nitration; Sulfonation;
Friedel Crafts Alkylation/acylation; Other alkylations
Nucleophilic Aromatic Substitution via Benzyne
Nucleophilic Aromatic Substitution via AdditionElimination
Acid-Base reactions of amines
Polyalkylation of ammonia, amines, and azide ion
(all SN2)
+
Formation of the nitrosyl cation (NO ).
Reactions of secondary amines with the nitrosyl
cation to give N-nitrosamines.
Reactions of primary amines with the nitrosyl cation
to give diazonium ions.
The Tiffeneau-Demjanov rearrangement
The Hofmann Elimination
The Cope elimination
The Heck Reaction
The Suzuki Coupling
Alkene Metathesis
The Diels-Alder Reaction
The Claisen Rearrangement
Cope Rearrangement
Acid-catalyzed formation of glycosides (review
acetal formation 16.8B, same reaction).

22.3A
22.3B

23

23.5-23.6
23.7A-B
23.8
23.8C
23.8D
23.8D
23.9
23.11

23.5-23.6
23.7A-B
23.8
23.8C
23.8D
23.8D
23.9
23.11

24

24.3B
24.4B
24.5C
24.6F
24.7A
24.7B
25.2A

24.3B
24.4B
24.5C
24.6F
24.7A
24.7B
25.2A

25

13

Beyond
25

26.4B/MoodleRooms
26.4B/MoodleRooms
MoodleRooms
MoodleRooms
MoodleRooms
MoodleRooms
27.4B/MoodleRooms
27.4B/MoodleRooms

26.4B/MoodleRooms
26.4B/MoodleRooms
MoodleRooms
MoodleRooms
MoodleRooms
MoodleRooms
27.4B/MoodleRooms
27.4B/MoodleRooms

Formation of dimethylallyl cation/Reaction to

geranyl pyrophosphate.
From Squalene to Lanosterol
+
Oxidation of an alcohol by NAD .
Unsaturated fatty acids from saturated fatty acids
using FAD oxidation.
Claisen reactions in biochemistry.
Reverse aldol reactions in biochemistry.
Cyanogen Bromide induced cleavage
Edman degradation.

Notice about Mechanism table:

Journal:

All mechanisms above must be represented in your reaction journal. Submit the journal entries on
exam day for the items above that are covered on that exam. Loose-leaf paper is fine (you dont need
a binder or cover). The Journal counts as 5% of your overall grade. Mechanism journals are
collected beginning with Test #2. Bring your journal to class on the day of the exam.

Frequently Asked Questions about the Mechanism Journal:

1.
When do I need to start my mechanism Journal?
Because there are only two items listed before Test #2, it is not worth setting up your
journal until Test #2. Dr. Whitaker will tell you how to start your journal as we get closer to
Test #2.
2.
What do I put in my Mechanism Journal?
Put at least one hand-written (YOUR HAND) example of a mechanism for each item in the
table above. Try to put it in there as soon as it is covered in lecture. Feel free to copy, by
hand, examples of mechanisms posted at MoodleRooms or in the text. Try to include
section numbers for each mechanism to help you organize for studying.
3.
When is the Mechanism Journal Due?
It is due the day of each exam. Material covered on that exam must be included in the
Journal. Often, Dr. Whitaker does not give the Journal back to you. This is a clever way to
force you to do the mechanisms OVER AGAIN. THE ONLY WAY TO LEARN MECHANISMS
IS THROUGH REPETITION.
4.
Why are mechanisms so important?
Understanding reaction mechanisms is like understanding how a machine or a tool works.
If you understand how it works then you can apply it to appropriate situations AND
manipulate it so that it works better.

On-Line Web Based Learning (OWL):

You have an OWL access card if you bought the book new from the bookstore (DO
NOT THROW IT OUT!). For those that bought the book used you need to go back to
the bookstore to purchase a separate OWL access card. The cost is roughly $40.

IMPORTANT NOTE: FOR THIS SEMESTER ONLY YOU ARE GOING

TO BE ENROLLING FOR OWL FOR A DIFFERENT TEXTBOOK (DO
NOT PURCHASE THIS TEXTBOOK). On-line access for the Online Web-Based
Learning (OWL) website (http://owl1.thomsonlearning.com/). You should enroll your OWL
access for the following textbook: W. H. Brown, C. S. Foote, B. L. Iverson, E. V. Anslyn Organic
Chemistry, 5th Ed. New York: Brooks/Cole, 2009.

Read the instructions on the access card VERY carefully and you
will have no trouble getting into the system. This is a very useful
resource that is a significant part of your course grade. It allows
you to do practice problems, get feedback, and do them again if you

14

got it wrong. By being patient and paying attention you will get a
good grade.
OWL Resources:
Students are provided with quick start guides for using the MarvinSketch
drawing tool, and getting started using OWL at: http://owl.cengage.com/ .
Students should go to this site during the first week to familiarize
themselves with OWL.
Grading OWL:
The OWL system tells me how many assignments you have completed.
Sometimes there are technical glitches that prevent certain assignments
from working. Just keep in mind, if you can complete 96% of the
assigned exercises successfully and on time, then you will get a perfect
OWL grade (10% of your course grade).
What do you do if you miss an OWL deadline?
I want everyone to do well with OWL. The best part about it is that you
get immediate feedback and the opportunity to correct your mistakes. I
realize that sometimes your busy schedule prevents you from getting to a
computer.
Heres what you do if you missed an OWL deadline:
1) Go to past due assignments and DO THE MISSED ASSIGNMENT.
Make sure you note the missed assignment number (ex. Ch 1 f). You
will now have a grade of check-minus (as opposed to check)
2) E-Mail me at the course gmail address (see the top of this handout).
Subject = Please grant me an extension for Assignment 1 f.
3) In the text for the email, give me your full name that you used to
register at OWL. I will then extend the deadline to the date of the email and your grade will automatically change from a check-minus to
a check.
I am very flexible giving extensions but there may be a limit for students
who are continuously requesting extensions.

There will be no extensions after the FINAL DAY

OF LECTURE!

15

STUDENT

CONDUCT POLICY

Cheating:
ACADEMIC HONESTY: Henry Ford Community College considers academic dishonesty to be a
serious offense. It is the policy of the College that determination of and appropriate action in
respect to academic dishonesty by a student shall be a matter of individual judgment by the
instructor. The instructor may administer a penalty up to and including failure in the particular
course. From: HFCC Catalog, Policy on Academic Dishonesty. Incidents of academic
dishonesty will be reported to the Registrar, who will maintain a file on each incident. Two
reported incidents will result in the students debarment from the college.
See attached copies on Academic Dishonesty and incidents of cheating.
Students Conduct:
Students must abide by the college's code of student conduct. See the attached excerpt from the
Code of Student Conduct.
Tape recording lectures without the faculty member's consent is prohibited.
Policy on Academic Dishonesty (Cheating)
Excerpted from HFCC Catalog: Henry Ford Community College considers academic dishonesty to be a
serious offense. It is the policy of the College that determination of and appropriate action in respect
to academic dishonesty by a student shall be a matter of individual judgment by the instructor. The
instructor may administer a penalty up to and including failure in the particular course. It is the
professional obligation of the faculty to enforce academic integrity in their courses.

Academic dishonesty is any activity intended to improve a students grade fraudulently.* It

includes, but is not limited to, the following:
1. Unauthorized acquisition of tests or alteration of grades (such as the stealing of tests,
test keys, or grade books from faculty offices or elsewhere, or the purchasing of
tests or grade books);
2. Unauthorized use of notes, books, or other prohibited materials during an examination;
3. Open cheating on an examination (such as copying from another students paper);
4. Permitting another person to take a test in the students place or receiving unauthorized
assistance with any work for which academic credit is received;
5. Providing unauthorized assistance with any work for which academic credit is
received;
6. Revision of graded work in an attempt to receive additional credit fraudulently;
7. Plagiarism (using another persons work without acknowledgment);
8. Any other conduct intended to obtain academic credit fraudulently or dishonestly.
If an instructor fails a student in a course for academic dishonesty, the instructor must
immediately notify in writing the student and the registrar of the infraction, retaining copies of
both notifications.
The registrar maintains a record of all such violations. If a student fails two classes as a result of
academic dishonesty, he or she is dismissed from the College for two academic years. In
addition, a notation of the reason for academic dismissal is placed on the students transcript.

16

The notation may be expunged at the discretion of the appropriate vice president if the student
petitions for its removal after at least two years have elapsed since the disciplinary action.
If a student believes that the accusation is false, he or she may appeal through the Student
Complaint Procedure. If the appeal reaches the Student Complaint Board, the Board may
consider only whether the charge is justified. The Board may not set aside or change the penalty
given by the instructor unless the charge of academic dishonesty is set aside.
*Any action that violates the Student Conduct Policy and Due Process Procedure is also subject
to review under that policy.

Excerpted from the HFCC Catalog:

RIGHTS AND RESPONSIBILITIES
Students have the rights and accept the responsibilities of participating in an educational
environment when they enroll at HFCC. Each student is expected to respect the rights of others and
to help create an environment where diversity of people and ideas is valued. A collegiate community
should be free from intimidation, discrimination, and harassment, as well as safe from violence.
Students are also expected to know and obey federal and state laws and local ordinances, as well as
be responsible for following College policies.
Students at HFCC have the same rights under the constitutions of our nation and state as other
citizens. These rights include freedom of expression, press, religion, and assembly. Freedom of
expression, for example, includes the expression of reasoned dissent and the voicing of unpopular
views. With every freedom goes the responsibility of according the same right to others. All students
have the right to be treated fairly and to have access to College policies. Students are entitled to
appropriate due process should they be accused of behavior that is in violation of laws or College
policy.
STUDENT CODE OF CONDUCT
A. Students at HFCC are expected to show respect for order, law, the personal rights of others, and
the educational mission of the College, as well as to maintain standards of personal integrity.
B. Behavior or situations that violate these standards include, but are not limited to:
1. interference with normal College or College sponsored activities, including, but not
limited to: teaching, College administration, and College Board meetings;
2. non-compliance with the directions of College personnel, including campus safety, or with
the orders of any College board, such as the Student Center Board;
3. violation of accepted standards of decency;
4. discrimination against an individual or group in any activity, opportunity, or organization
on the basis of race, ethnicity, gender, religion, sexual orientation, creed, national
origin, ancestry, age, disability, height, weight, or marital status;
5. harassment that interferes with an individuals work or educational performance;
6. physical assault;
7. stalking;
8. threats of injury or harm;
17

9. arson;
10. theft;
11. gambling;
12. property damage;
13. possession of firearms or dangerous weapons;
14. possession, use, or distribution of alcohol or illegal drugs.

The complete text of this policy is available in the office of the Vice President/Dean of Student
Services, 430A Administrative Services and Conference Center.
Alcoholic Beverages and Illegal Drugs
Use, possession, or distribution of alcoholic beverages and drugs is forbidden on campus. Persons
appearing on campus while under the influence of alcoholic beverages, narcotics, and other
dangerous drugs, except as expressly permitted by law, will be subject to disciplinary and/or legal
action.
Possession, consumption, sale, or purchase of any controlled substance which is illegal under state or
federal law is prohibited on the campus of Henry Ford Community College.
Campus Attire
Students are expected to use good judgment, good taste, and decency with regard to their selection of
dress.
Attendance

No system of cuts operates at Henry Ford Community College.

Students are expected to attend all the sessions of the classes for which they are enrolled.
Penalties may be imposed, at the discretion of the individual instructor, whenever the quality
of the students work has been affected by absence or tardiness.
Students, as a matter of courtesy, should explain the reason for an absence to their
instructors. Lack of attendance may affect the students final grade.
Absences in connection with participation in authorized college activities must be considered
in the total picture of absences for all purposes, and it is the responsibility of the student to
make up work missed.
Students are required to be present at the final examination. In case of absence, it is the
students responsibility to contact the instructor in regard to makeup.

18

An Open Letter to HFC Math and Science Students:

We have had a sudden increase in incidents of cheating among students in science courses. Cheating is defined in the Policy on
Academic Dishonesty, and applies to tests, quizzes and exams, to in-class and out-of-class assignments, and to any other aspect of
class for which you receive credit toward a grade. We consider cheating in class to be a very serious offense.
There are many ways students can cheat in class, some of which are quite sophisticated. Here are some recent examples of
cheating on Tests, Quizzes, or Exams:
Communicating, or appearing to communicate with another person:
Talking (no matter what you say)
Passing notes (no matter what is on the note)
Using suspicious signals of any sort (hand signals, tapping pencils, sniffing, etc.)
Sharing calculators or other implements (no matter what is on it)
Using cell phones, PDAs or similar items for any reason (even if it is only for the calculator function).
Sharing any items your instructor allows individual students to bring into the exam.
Sharing or appearing to share information:
Copying from another persons paper
Allowing another person to look at your paper
Looking at another persons paper
Appearing to look at another persons paper
Possessing a prohibited item or information (even if you do not use it):
Any notes you are not specifically permitted to bring with you
Any permitted sheet that contains any non permissible information (e.g., your instructor says you may have only
equations on an equation sheet and you have anything else written on it.)
Notes written on your clothing, your body, or anywhere else (no matter what they say).
Using calculators, etc. other than those specified by the instructor.
Assisting other students:
Creating a diversion that allows other people to cheat by distracting the proctor.
Passing information about an exam to students who have not yet taken it.
Taking an exam for another student.
Contrary to popular belief, the proctor does not have to catch you in the act of cheating they may discover it beforehand, later, or
while grading. The same rules apply.
Students who cheat or assist others in cheating will be subject to academic penalties up to and including failure in the course.
Incidents of cheating reported to my office will be forwarded to the Registrar for action. Two reports to the Registrar will result in
your being barred from the College.
Instructors have the duty to enforce general test-taking conditions to ensure the integrity of exams. They may use generally
accepted security practices in carrying out this duty, including assigning seats, restricting access to the room, setting the rules for
answering questions during the exam (or refusing to answer them), enforcing reasonable dress codes (e.g., no ball caps, no jackets,
etc.), requiring photo identification, specifying exactly what items you are allowed to have with you at the exam, and examining
any items you have with you (whether they are allowed or not). If you do anything that appears to be cheating, they have a duty to
confiscate your exam and enforce the cheating policy without further notice.
You have been warned. If you dont do these things, you wont have a problem. If you do these things, you cant plead ignorance.
Janice Gilliland
Associate Dean of Math and Science

19

STATEMENT OF RECEIPT OF COURSE SYLLABUS

I have received a copy of the syllabus for Chemistry 242, Section 1 and agree to abide by its
terms and conditions.
I have also read the Policy on Academic Dishonesty, the Student Conduct Policy, and the Open
Letter to HFCC Science Students and agree to abide by their terms.

________________________________________
Students Signature
Date

________________________________________
Students Name (printed)
Date

This page must be submitted to the instructor BEFORE YOU TAKE THE FIRST TEST.

20