Download Chemistry 231 – Organic Chemistry I

Chemistry 231, Organic Chemistry I
Syllabus
Hofferberth, Fall 2011
Chemistry 231 – Organic Chemistry I
Course Description:
Organic chemistry is the study of the structure, properties, and reactions of molecules containing carbon.
The prominence of carbon containing molecules, organic molecules, in our everyday life may explain
why organic chemistry is such a rich discipline. Much of what we wear, smell, eat, build, burn, and
touch during our lives is composed of organic molecules. We ourselves and all other life we know are
based on compounds of carbon.
Why has carbon adopted such a central role in our lives and life itself? One reason is that carbon is a
versatile and promiscuous element. It is capable of bonding to itself and other elements in a multitude of
ways. One indication of carbon’s versatility is the fact that more than 14 million organic compounds
have been described and hundreds of novel compounds are being prepared or discovered every month.
This course is the first of a two-course sequence designed to introduce students to the theoretical
underpinnings of organic chemistry. We will begin by exploring how organic molecules are held
together and learn to recognize the key functional groups. For the remainder of the year, we will take an
in-depth look at the chemistry and properties of a number of functional groups. During our study you
will acquire the tools to design a synthesis for simple organic molecules. You will also learn how to
employ familiar concepts from thermodynamics and kinetics to predict both the products that are likely
to form in an organic reaction and the detailed course of events that leads to their formation.
Instructor and Resources:
Instructor:
Email:
Office:
Office Hours:
Lecture Hall:
Class Time:
Text:
Materials:
Website:
Dr. John Hofferberth
[email protected]
312 Tomsich Hall
Monday 2 – 4 PM, Wednesday 10 – 11 AM, Friday 2 – 4 PM
Hayes 109
9:10 – 10:00 AM, MWF
Organic Chemistry, 5th Ed, Vollhardt and Shore (optional study guide)
HGS Molecular Structure Model (Kit C)
moodle.kenyon.edu (search for Chemistry 231 once you have logged in)
Course Policies and Expectations:
Course Grade:
Your grade in the course will be determined by your homework binder and
performance on quizzes, midterms and the final. The point breakdown that
will be used is provided below:
Chemistry 231, Organic Chemistry I
Syllabus
Quizzes (10 × 5 pts)
Midterm Exams (3 × 100 pts)
Final Exam
Homework Binder (3 × 20 pts)
Participation and Preparation
Total Points
Hofferberth, Fall 2011
50 pts
300 pts
150 pts
60 pts
20 pts
580 pts
The following absolute grading scheme will be followed to determine your
final grade:
Attendance:
Grade
Percent of Total Points Earned
A (+/-)
100% - 90%
B (+/-)
89% - 80%
C (+/-)
79% - 70%
D (+/-)
69% - 60%
F
< 60%
Your attendance at every lecture is expected.
You will be permitted three unexcused absences. Every absence thereafter will
result in a grade reduction of 1/2 of a letter grade (29 pts) for the course. You
will be expelled from the course after six unexcused absences.
Preparation:
The material in this course builds on itself. For that reason it is imperative
that you keep up with the lecture.
Strongly suggested study habits:
1) Neatly recopy and annotate course notes with material from the text, course
web page, and other resources after every lecture.
2) Complete as many practice problems as you can. The suggested homework
problems indicated on the course schedule represent the bare minimum
preparation for the course. You will be required to maintain an organized
homework binder which should contain all of the practice problems you
work on. Revisiting practice problem from previous topics is a good way to
assure that you have retained the key information.
3) Keep up with all aspects of the course and seek help quickly if questions
arise.
You can get help on any aspect of the course 6 days a week from:
1) The instructor (Office Hours, Sunday Review Sessions – see below)
2) The Math and Science Skills Center (101 Tomsich; Sunday, Tuesday, and
Chemistry 231, Organic Chemistry I
Syllabus
Hofferberth, Fall 2011
Thursday 7:00 - 10:00 PM). There should always be a tutor able to help
with organic questions available at the MSSC. We will also have a lead
tutor for this class, Lars Matkin, who will hold two office hours each week
at the MSSC (TBD).
Sunday Evening
Review Sessions:
Dr. Hofferberth will lead a weekly review session on Sunday evenings
between 6:00 and 7:00 PM in Tomsich 101. These sessions are entirely
optional and the content will be directed by student questions. The review
sessions will end promptly at 7:00 PM and students with additional questions
can make use of the Sunday hours for the Math and Science Skills Center
(7:00 – 10:00 PM). If these sessions are poorly attended the instructor
reserves the right to discontinue them.
Suggested
Problems:
The best way to master organic chemistry is to practice. A reading assignment
and suggested problems will be indicated on the syllabus for each topic
covered in lecture. You will organize all of the practice problems you
complete into a ‘homework binder’ that will be collected at each midterm
exam. The instructor will spot-check a few of the problems suggested since
the last exam and will assign a grade out of 20 points based on the completion
(10 pts) and correctness (10 pts) of the problems he checks. Mastering the
suggested problems is key to success on quizzes and examinations. Revisiting
suggested problems will increase comprehension, build confidence, and
increase your speed in responding to exam questions.
Working additional problems in the text (or in other organic chemistry texts) is
a valuable use of your preparation time for this class. Suggested problems will
appear on quizzes and exams.
Quizzes:
Ten quizzes will be given during the semester (dates indicated on the
schedule). Each quiz will be composed of a suggested problem that has been
assigned since the last quiz. Quizzes will begin at 9:10 AM and end at 9:15
AM. There will be no extra time or make-up quizzes given, however, your
lowest quiz score for the semester will be replaced by your highest quiz score.
Midterm Exams:
Three in-class midterm examinations will be given during the semester (dates
indicated on the syllabus). Seating for the in-class portion of the exam will be
assigned by the instructor as students enter the exam room. Model kits may be
used on all exams in this course. If you have a conflict with any of the exam
times you must notify Dr. Hofferberth in writing at least one week prior to the
exam to schedule an alternate exam time.
Chemistry 231, Organic Chemistry I
Syllabus
Final Exam:
Hofferberth, Fall 2011
The final exam for the course will be cumulative and closed-note. The final
exam will be held on December 12th from 1:30 to 4:30 PM.
Accommodations: In accord with Section 504 of the Rehabilitation Act of 1973 and the
Americans with Disabilities Act of 1990: If you have a disability and need
accommodation in order to fully participate in this class, please identify
yourself to Erin Salva, Coordinator of Disability Services (PBX 5145,
[email protected]). All information and documentation of disability is
confidential. The instructor must receive information regarding the nature of
the accommodation directly from Erin Salva and speak to you about the
accommodation at least one week in advance of an exam or quiz so that
arrangements can be made for the accommodation.
Academic
Integrity:
Academic integrity is expected in all aspects of this course. A detailed
description of academic integrity and the College policy regarding academic
dishonesty can be found in the Course Catalog at the following link:
http://www.kenyon.edu/x11747
Electronic Device Full engagement with the lecture portion of this course will be a key
Policy:
component of success. All electronic devices should be turned off before the
beginning of every lecture.
Tentative Schedule:
Date
8/26
9/5
Topic
Introduction,
Bonding Review
Bonding Models
Resonance,
Representations of
Organic Molecules,
and Functional
Groups
Kinetics, TD’s,
Acids and Bases,
Electrophiles and
Nucleophiles
Quiz 1
9/7
Alkanes,
Nomenclature, and
Conformational
Analysis
Alkanes
8/29
8/31
9/2
Reading (Suggested Problems)
1.1-1.4 (1.21-1.24, 1.29)
1.6-1.8 (1.31)
1.5, 1.9, 2.3 (1.25, 1.27, 1.32, 1.33, 1.35, 1.37, 1.39,
2.27, 2.39)
2.1-2.2 (2.22-2.24, 2.26)
2.4, 2.5, 2.7 (2.29-2.31)
Chemistry 231, Organic Chemistry I
Syllabus
9/9
9/12
9/14
9/16
9/19
9/21
9/23
9/26
9/28
9/30
10/3
Conformational
Analysis
Quiz 2
Bond Strength,
Radicals
Radical
Halogenation,
Hammond’s
Postulate
Radical
Halogenation,
Combustion
Quiz 3
Cycloalkanes,
Nomenclature,
Ring Strain
Cycloalkanes,
Conformational
Analysis
Exam I
Cycloalkanes
Isomer Hierarchy,
Chiral Molecules,
Absolute
Configuration and
Optical Activity
Diastereomers and
Meso Compounds
Quiz 4
2.8 (2.35-2.37)
3.1, 3.2, 3.4 (3.13, 3.14, 3.17)
3.5 – 3.7 (3.18 – 3.25)
3.8 – 3.10 (3.26, 3.27, 3.31, 3.32, 3.33)
4.1 – 4.3 (4.17 – 4.20)
4.5 (4.21 - 4.23)
4.6 (4.24 – 4.26, 4.30, 4.32)
5.1 – 5.3 (5.28-5.32)
5.5, 5.6 (5.34 – 5.36)
5.7 (5.38, 5.41 – 5.43)
10/7
10/10
Stereoselectivity
Stereoselectivity
and
Enantioselectivity
Fall Break
Quiz 5
6.1 – 6.5 (6.27 – 6.29, 6.32, 6.34)
10/12
10/14
10/17
Haloalkanes/SN2
SN2
SN2 and SN1
Quiz 6
6.6 – 6.9 (6.35 – 6.38, 6.40 – 6.45)
7.1 – 7.3 (6.48 – 6.50)
7.4 – 7.5 (6.51, 6.52, 7.22 – 7.25)
10/19
SN1
E1 and E2
7.6 (7.26 – 7.32)
10/5
Hofferberth, Fall 2011
Chemistry 231, Organic Chemistry I
Syllabus
10/21
10/24
10/26
10/28
10/31
Hofferberth, Fall 2011
Exam 2
Competition
Quiz 7
11.9 – 11.11 (7.33-7.35, 11.45)
(7.36 – 7.43)
(11.47 – 11.49, 11.51, 11.52, 11.57, 11.58)
8.1 – 8.5 (8.21 – 8.25)
Alcohols
11/2
11/4
11/7
11/19
11/11
11/14
11/16
11/18
11/28
11/30
12/2
12/5
Quiz 8
Reactions of
Alcohols
Reactions of
Alcohols (Ethers)
Reactions of
Alcohols
Quiz 9
Alkenes
Rxns of Alkenes
Exam 3
Quiz 10
8.6 – 8.9 (8.26, 8.30, 8.31)
(8.32 – 8.35)
9.1 – 9.4 (9.25 – 9.30, 9.32)
9.5 – 9.9 (9.34 -9.37, 9.39, 9.40)
9.10 (9.41 – 9.44, 9.49, 9.55)
11.1-11.3 (11.26, 11.27, 11.30)
12.1-12.5 (12.27, 12.29, 12.31i, 12.32)
12.7-12.8 (12.33, 12.34, 12.36)
12.9-12.11 (12.37, 12.38)
12.12-12.14 (12.39-41, 12.45-47)
13.1, 13.2, 13.4, 13.5 (12.48, 13.21, 13.22, 13.25,
13.27, 13.30)
Alkynes
12/7
12/9
12/12
13.6 – 13.8 (13.32, 13.33, 13.34)
Study !!
Wrap-Up and
Evaluations
Final Exam – 1:30-4:30 PM