Chemistry 222-D – Organic Reactions and Synthesis – Spring, 2022 (01/17/22 – 05/01/22)
Classes will be in-person
Instructor:
Valentine St. Hilaire: Lecture Hall: Knight Physics 112: M/W/F @ 11:15 am – 12:05 am
Office Cox 350. Office Phone: (305) 284-4004
e-mail: vxs314@miami.edu; sthilaire@miami.edu
Teaching
Assistants:
Briana Bernard, bxb653@miami.edu
Wilson Kovacs, rsw94@miami.edu
Office Hours: Sessions are in-person and remote and accessible via Zoom: Zoom links will be posted to class portal.
Monday/Wednesday: 12:30 PM to 1:00 PM
Friday: 1:00 PM to 2:30 PM (online via Zoom)
Tuesday/Thursday: 10:00 AM to 12:00 Noon…and by appointment. Contact by email to
schedule (evening and weekend hours available).
Text:
Organic Chemistry, 3rd Edition by David Klein, published by WILEY
ISBN: 978-1-119-11047-7 (any format) hard cover, paper back, loose-leaf or digital copy)
Study Guide/Solution manual (not required)
Molecular models: Darling molecular vision Kit #1 (green box)
Organic chemistry as a second language, 2nd semester topics, 3rd Edition by David Klein
(recommended)
Supplementary Top Hat Learning (~$30) join Code 597817 See page 3 for details
Material:
Achieve (~$30) See page 3 for details
Lectures:
Note that all lectures will be in-person, with live video access to recordings of all presented lectures.
Lectures can be accessed via BlackBoard Collaborate Ultra (or Zoom if a switch is deemed necessary).
Instructions for Student log-in and lecture retrieval have been posted to the class portal on
BlackBoard. No download is required to use BlackBoard Collaborate or for accessing Zoom through
our class portal. In the event of a zoom lecture, additional log-in information will be sent via email
and also posted to BlackBoard.
Homework:
Homework will be completed online as ‘Supplementary Material’ with Achieve (from Macmillan
Learning). The due dates for each homework will accompany each assignment. Homework will
account for 10% of the final grade. No makeup homework assignments will be given. Technical
difficulties are monitored at the server; thus any personal technical difficulties are not justification
for due date extensions.
Exams:
Four exams will be held: February 24, March 24, April 14, and May 3 (Final exam). All Exams
will be in-person during the Friday 5:00 pm to 6:30 pm timeslot. Additional instructions will be
posted to BlackBoard, as necessary, if exams are to be taken remotely. Please see class portal for
instructions on downloading the specific browser needed for taking the exams remotely. Students
have 96 hours after the return of an exam to bring any grading errors to the attention of the Instructor.
After that 96-hour period, no re-grades will be considered.
Final Exam:
Monday, May 3rd (8:00 am to 10:30 am)
Recitation:
Recitation will account for 10% of the final grade. Note that your active participation in discussions
and problem-solving during recitation will be noted and factored into your recitation grade. Notify
the instructor if, for any reason, you are unable to attend recitation as scheduled. Recitation Log-in
will be as for lecture with instructions posted to BlackBoard.
Workshops:
Workshops are highly recommended. A schedule of Workshop Leaders and available times will be
posted to the class portal. Attendance of at least one session per week amounting to 80% of the total
number of weeks will result in a 0.5% bonus to your overall semester cumulative score.
Grading:
Your grade will be based on the following:
Three mid-term exams
Cumulative final exam
Recitation: attendance/quizzes
Achieve (homework)
Total
* (lowest mid-term score will be dropped)
50% (25% each) *
30%
10%
10%
100%
Grading Scale:
A+ 98-100
A 93-97.9
A− 90-92.9
Incompletes:
An "I” grade will only be considered for an extremely compelling reason.
Drops:
Wednesday, February 1 is the last day to drop without a W; Wednesday, March 29 is the last day
to drop with a W
Cheating:
Cheating will not be tolerated, and the University of Miami undergraduate honor code will apply
(http://www.miami.edu/sa/index.php/policies_and_procedures/honor_code/).
It
is
the
responsibility of all students in the class to read, understand, and uphold the honor code. As a
reminder, upon submitting completed exams to the proctor, you will be asked to show your photo
ID (Cane-Card).
Attendance:
It is in the student’s best interest to attend all classes. The student should inform the instructor of
any known class absences as soon as possible. All planned absences should be sent to the professor
by email.
B+ 88-89.9
B 83-87.9
B− 80-82.9
C+ 78-79.9
C 73-77.9
C− 70-72.9
D+ 68-69.9
D 60-67.9
F <60
E-mail Protocol: Please allow up to 24 hours for an email response.
Disability
Services:
The Office of Disability Services (ODS) is the primary university office responsible for the
coordination of auxiliary aids and services for students with disabilities. Individuals with
disabilities must request academic accommodations through ODS, located in the Camner
Academic Resource Center in Whitten University Center N201. ODS staff can be reached at 305284-2374 (voice), 305-284-3401 (TDD). During the normal school year, office hours are from 8:30
am to 5:00 pm Monday through Friday. You may email office at disabilityservices@miami.edu
Calculators:
CELL PHONES AND PROGRAMABLE CALULATORS ARE NOT ALLOWED ON
EXAMS OR QUIZZES. In extreme circumstances, if you are verifiably able to clear the memory
cache of your programmable calculator, you could be allowed to use it during an exam.
Missed Exams:
Make-up examinations will NOT be offered. It will NOT be possible to take exams AFTER the
regular exam time. If you know in advance that you will be missing an exam due to universityapproved reasons, you may make arrangements with the instructor (at least a week in advance) to
replace the exam using the Exam Replacement Policy (see below). Any student absent from class
in observance of a religious holy day shall not be penalized; however, it is the student’s obligation
to provide faculty members with notice of the dates they will be absent due to observance of
religious holy days, preferably before the beginning of classes, but no later than the end of the first
three class days.
Signing up
We will be using the Top Hat (www.tophat.com) system for daily attendance and classroom
for Top Hat
response. You will be able to submit answers to in-class questions using Apple or Android
smartphones and tablets, laptops, or through text message.
You will be able to submit answers to in-class questions using Apple or Android smartphones and tablets,
laptops, or through text message. You can visit the Top Hat Overview
(https://success.tophat.com/s/article/Student-Top-Hat-Overview-and-Getting-Started-Guide) within the Top
Hat Success Center which outlines how you will register for a Top Hat account, as well as providing a brief
overview to get you up and running on the system.
Top Hat will require a paid subscription, and a full breakdown of all subscription options available can be found
here: www.tophat.com/pricing. You subscription should cost $30 for 4 months ($48 for 1 year). Do not worry if
you do not see any content in the course right away, I will make it available to you as we progress through the
semester.
Note: The Course Join Code for CHM 222-D is 246419
The join code should direct you to the appropriate subscription option. Do not worry if you do not see any
content in the course right away, I will make it available to you as we progress through the semester. YOU
SHOULD NOT HAVE TO PAY MORE THAN $30 (+ applicable taxes) for this package.
Should you require assistance with Top Hat at any time, due to the fact that they require specific user information
to troubleshoot these issues, please contact their Support Team directly by way of email (support@tophat.com),
the in app support button, or by calling 1-888-663-5491.
Additionally, please let me know of any technical issues: especially ones that result in missed or late
assignments.
Some links on how to use the various TopHat features properly:
https://support.tophat.com/s/article/Student-Secure-Attendance
https://support.tophat.com/s/article/Student-Secure-Attendance-Browser-Permissions
https://support.tophat.com/s/article/Student-Secure-Attendance-Mobile-Permissions
Signing up
for Achieve
We will be using Achieve (achieve.macmillanlearning.com.) for homework
Use the following invite link https://achieve.macmillanlearning.com/courses/5eyunu/mycourse
to purchase a subscription, sign up/create an account. If you already have a Macmillan
Learning account, you can log in with your existing credentials. The course will be described with
CHM222 B & D: Organic Reaction and Synthesis SPRING 2023.
Additional sign-up instructions can be found by clicking on the following link:
https://macmillan.force.com/macmillanlearning/s/article/Achieve-Access-Code-FAQ#signin
Daily Lecture Topic Guide (may vary slightly, exams dates will not)
Date
Topic
Chapter(s)
01/18/2022
Introduction/Review Material
7, 8, 9
01/20/2022
01/23/2022
01/25/2022
01/27/2022
01/30/2022
02/01/2022
02/03/2022
02/06/2022
02/08/2022
02/10/2022
02/13/2022
02/15/2022
02/17/2022
02/20/2022
02/22/2022
02/24/2022
02/24/2022
02/27/2022
03/01/2022
03/03/2022
03/06/2022
03/08/2022
03/10/2022
03/20/2022
03/22/2022
03/24/2022
03/24/2022
03/27/2022
03/29/2022
03/31/2022
04/03/2022
04/05/2022
04/07/2022
04/10/2022
04/12/2022
04/14/2022
04/14/2022
04/17/2022
04/19/2022
04/21/2022
04/24/2022
04/26/2022
04/28/2022
Comments
See review slides/content posted to
BlackBoard
“
Sections 10.1 – 10.13,
Section 10.4 (qualitative approach)
Review Material/Radical Chemistry
7, 8, 9
Radical Chemistry
10
Radical Chemistry
10
Radical Chemistry/Synthesis
10/11
Sections 11.1 – 11.4, 12.1 – 12.3
Introduce Grignard Reaction (Section 12.6)
Synthesis
11
Sections 11.5 – 11.7
Synthesis/Alcohols and Phenols
11/12
12.1 – 12.3
Alcohols and Phenols
12
Sections 12.4 –12.7
Alcohols and Phenols
12
Sections 12.8 – 12.10, 12.12
Ethers and Epoxides
12/13
Section 13.1 – 13.5
Ethers and Epoxides
13
Section 13.5 – 13.10
Ethers and Epoxides
13
Section 13.10 – 13.12
IR Spectroscopy/Review (Chapters 10 – 13)
14
Section 14.1 – 14.4
IR & Mass Spectroscopy
14
Section 14.5 – 14.9, 14.16
NMR Spectroscopy
15
Section 15.1 – 15.5
NMR Spectroscopy
15
Section 15.5 – 15.9
MidTerm Exam 1: (Chapters, 10 – 13) (5:00 – 6:30 pm). See posted study guide for details
NMR Spectroscopy
15
Section 15.9 – 15.13
NMR Spectroscopy/NMR Integrated
15
Section 15.1 – 15.13
problem solving
NMR Spectroscopy/NMR Integrated
15/16
Sections 16.1 – 16.4
problem solving
Conjugated Pi Systems
16
Sections 16.1 – 16.4
Molecular Orbitals/
16
Sections 16.3 – 16.7
Conjugated Pi Systems
16
Sections 16.7 – 16.10
Spring Recess 03/11/2022 — 03/19/2022
Conjugated Pi Systems /Aromatic
16/17
Sections 16.11
Compounds
Aromatic Compounds
17
Sections 17.2 – 17.5
Aromatic Compounds/(Review 14 – 17)
17
Sections 17.5 – 17.8
MidTerm Exam 2 (Chapters, 14 – 17) (5:00 – 6:30 pm). See posted study guide for details
Aromatic Substitution Reaction
17/18
Sections 18.1 – 18.5
Aromatic Substitution Reaction
18
Sections 18.5 – 18.10
Aromatic Substitution Reaction/ Review
18
Sections 18.10 – 18.15
Aldehydes and Ketones
19
Sections 19.1 – 19.5
Aldehydes and Ketones
19
Sections 19.5 – 19.8
Aldehydes and Ketones
19
Sections 19.8 – 19.12
Carboxylic acids and Their Derivatives
20
Sections 20.1 – 21.5
Carboxylic acids and Their Derivatives
20
Sections 20.5 – 20.10
Carboxylic acids and Their Derivatives
20
Sections 20.10 – 20.14
MidTerm Exam 3 (Chapters, 18 – 20) (5:00 – 6:30 pm). See posted study guide for details
α-Carbon Chemistry (Enols & Enolates)
21
Sections 21.1
α-Carbon Chemistry (Enols & Enolates)
21
Sections 21.1 – 21.3
α-Carbon Chemistry (Enols & Enolates)
21
Sections 21.3 – 21.5
α-Carbon Chemistry (Enols & Enolates)
21
Sections 21.5 – 21.7
Summary of Nitrogen Chemistry
22
Sections 22.4 – 22.7
Carbohydrates
24
Sections 24.1 – 24.2
05/01/2022
05/02/2022
05/03/2022
05/15/2022
05/17/2022
Carbohydrates/Review of selected topics
24
Sections 24.5 – 24.6,
Reading Day
Final Exam (Cumulative) 8:00 PM – 10:30 PM
Session Grades submitted to Registrar’s Office by Instructor
Session Grades released by the Registrar’s Office in CaneLink
Student Learning Outcomes
1. Recognize reactive sites, describe reactivity and predict reactions. For a given structure, be
able to recognize reactivity in terms of nucleophilicity and electrophilicity of functional groups.
2. Construct reaction mechanisms based on electronic interactions and bond
formation/breaking. For a given reaction, be able to construct the steps of a reaction
mechanism. Be able to recognize alternate routes, possible rearrangements and side products.
3. Describe reactions in terms of energetic states and relative stability of products and
reactants. Be able to map reaction mechanisms, including starting materials, intermediates,
transitions states and products to an energy profile.
4. Keep detailed records of your problem-solving attempts. These will be useful when you seek
assistance from your instructor.
5. Build your own reaction summary pages/flow charts (for practice and for later review).
Miscellaneous Important Information copied from Dr. Colonna’s Syllabus
How to Survive and Excel in Organic Chemistry this spring:
1- CHM222 is very fast paced with LOTS OF REACTIONS, and requires A LOT of practice and dedication.
2- Important skills you need to master: Problem solving, time management, self-motivation, and good study
habits.
3- Be prepared to give a lot of time and effort to this class. In addition to class time, you should dedicate at least
4 hours a day of study time.
4- FORM A STUDY GROUP, it should not be hard! Multiple brains working on a problem is always better than
one. In addition, if you can teach someone else the material you KNOW the material.
5- Come to class!
6- Work all the assigned book problems, do the homework assignments, and of course do the practice problems
I give you in class. THESE ARE USED as a template for exam questions. Do not fake yourself out into thinking
you know how to work the problems (THIS IS VERY COMMON!), when really all you did was copy down the
answers from the solution manual or the answers found online. The more problems you work the more successful
you’ll be. REPETITION is the only way to retain o information!
7- Do the assigned reading BEFORE class and review your class notes directly after class. This will be a very
interactive class. Repetition of the material helps it to store in your long-term memory, which makes it easier for
you to ‘recall’ during a test. Many students find making note cards is extremely helpful for this class (these are
VERY useful for reactions!). Do not attempt Homework and problems until you have fully understood the
THEORY!
8- Please let me know if you are repeating the course. It is very possible that you could earn the same grade unless
you make some drastic changes. Let me work with you on this.
9- Not everyone will make an A. Many students stress about “I need an A for this….” Your goal in this class is
to be as successful as you can. Each test is a chance for you to show me what you have learned in the class up to
that point.
10- If you do poorly on a test question, learn from your mistake! Make an effort to review the graded exam during
OFFICE HOURS, don’t just assume you’ll do better in the next one…..The material in this class builds on itself.
You cannot expect to master the next test material until you have mastered the material that preceded it. Keys for
old exams will be available AFTER you attempt to rework the problem.
11- Start Studying NOW!! You cannot cram for this class! Falling behind will be detrimental to your grade!
12- If you are feeling totally lost lean on the students in your study group, see if they can help you. Talk to me
about lecture notes, your exams, ways to study etc…