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Chemistry 232
Organic Chemistry
Summer 2016
This course is a continuation of Chemistry 231 (Introductory Organic Chemistry), and completes
the second half of a full academic year of basic organic chemistry. Chemistry 232 is now the
same course as Chemistry 235, so the number doesn’t matter. In addition to completing a survey
of organic functional groups, the concepts of synthetic methodology, carbanions, -conjugation,
aromaticity, and the chemistry of benzene will be introduced.
Lecturer: Dr. Peter Marrs, Elliott 334c (my office, at the south end of the third floor) or Elliott
339 (my lab), pmarrs@uvic.ca. I am also the Senior Laboratory Instructor in charge of the
Chemistry 232 laboratory. I will have specific office hours for Chem 232 from 10:00–11:00
am on Tuesdays, 10:30–11:30 am on Wednesdays, and I am around and available at most
times. Please feel free to come by at any time (really!), or to make an appointment. You
can also contact me by e-mail.
Prerequisites: Chemistry 231 is the prerequisites for this course. Students must ensure that they
have the proper prerequisites; they will be de-registered without warning at any time if
found not to have the required courses.
Textbook: Organic Chemistry, Eleventh Edition, Solomons, Fryhle and Snyder, Wiley, 2014.
Students who already have the tenth edition may continue to use it for this course. If you
use the tenth edition, you will still need to purchase a code for WileyPlus, as there are assignments made using that web site. The library has other introductory organic chemistry
texts that offer a (somewhat) different perspective on the topics covered in Chemistry 232.
The Chem 231/232 Bundle contains the course material for the lecture portion. If you previously purchased the bundle for either course, it’s still good.
Included in the bundle is the Chem 231/232 Lecture Book. This is a compliment to the
textbook, not a replacement! The lecture book contains extra informative slides, useful
learning methods and other sample problems.
There is an access code for WileyPlus. The link for our course is: http://edugen.wileyplus.com/edugen/class/cls509864. Bookmark it! If you already created an account you
can re-use your login and password from previous Chem 231 or Chem 232 courses. Once
online, you can access the full electronic version of the textbook, and the required assignments. Other learning tools are available, so take a good look around!
The Solutions Manual is highly recommended, and available through VitalSource Bookshelf. In the bundle there is an access code which provides you with the electronic version
of the solutions manual in pdf form. This is installed directly on your computer and is not
accessible on-line.
As an alternative, David Klein’s “Organic Chemistry As a Second Language” books, terms
I and II, may be useful. A molecular model kit may also prove useful at times, but won’t
be required for any exams.
Laboratory: You are required to be co-registered in a laboratory section of Chemistry 232 while
you are registered in the lecture. A current laboratory manual (goldenrod cover) is required, and is available in the bookstore. Laboratories start the week of May 2. Students
who have previously passed the laboratory portion of either Chemistry 232 or 235 may
apply for a passed lab credit by contacting me.
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There is an update to the schedule in the lab manual, which has been e-mailed to you. The
laboratory is held in Elliott 347, and you will be following the experiment sequence for
that room.
Web sites: Lecture: http://web.uvic.ca/~pmarrs/chem232/. The link to the laboratory web
site is at the top of that page. WileyPlus: http://edugen.wileyplus.com/edugen/class/
cls509864.
E-mail: I use e-mail about once per week for updates and reminders to the class about lecture and
laboratory deadlines, and to provide extra useful information about the course. I get the
e-mail addresses from UVic, using whatever you provided to UVic as your “preferred”
e-mail, so ensure that it’s an address that you read often. Hotmail addresses often consider my mailings as “spam”, so please ensure you set @uvic to your safe senders list.
Missing an e-mail reminder is not an excuse for missing a deadline!
Grading: The grading formula consists of two main components; laboratory and lecture. The breakdown of the
laboratory mark is covered on the lab web site. The
lecture component consists of online assignments
(about eight), in-class quizzes (five) and the final
exam. The percentage component of each is shown
in the table at right. Both the lecture and laboratory
portions of the course must be passed independently of each other in order to successfully complete
the course.
1)
Component
%
Laboratory
33
Online assignments at
WileyPlus
In-class quizzes; best 4
of 5 @ 6% each
Final Exam
5
24
Total
100
38
On-line assignments are compulsory. These assignments are done through WileyPlus.
Each assignment consists of 15–20 multiple choice or text-entry questions. These are
marked by WileyPlus, the mark converted to a %, and your final % will be converted to a
mark out of 5. Deadlines for the assignments will be announced later, and you will have
plenty of time to complete the assignment.
I recommend that you do the quizzes as the material is presented in class, and avoid waiting until the last possible day. I will NOT accept any excuse—including computer breakdowns, software issues, or even health issues—for failing to complete the assignment, as
you have plenty of time to sort out the problems or access publicly available computer.
2)
In-class quizzes are compulsory. Quizzes will be written at the start of the class on the
scheduled day. The remainder of the period will continue the lecture sequence. The best
four of the five quizzes count towards the lecture grade. The final exam mark will not,
under any circumstances, be taken as a replacement for any quiz mark.
3)
The mark for any quiz or exam which is not written, and for which no official medical
excuse is provided will be zero. The excuse must be dated within the week of the quiz and
must be handed in within two weeks of the quiz date. The medical excuse must provide
sufficient information to establish that the student was not able to write the quiz or
exam due to his/her medical condition on the date of the quiz or exam in question. The
student will also be required to give written consent for information about her/his medical condition to be disclosed to the instructor. Any such information obtained is treated as
confidential. Certain other types of personal or family circumstances may be considered
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as equivalent to a medical excuse if accompanied by appropriate documentation. There
is no requirement to provide make-up quizzes. Students with medical excuses for missed
quizzes will have their quiz scores averaged on the remaining quizzes written. Quiz writing time is up to 25 minutes during a regular lecture period.
4)
The assignments test your basic knowledge of the material in each chapter (or two). The
quizzes will test both basic and a more in-depth knowledge of the material covered over
a short span of chapters/sections. The final examination will cover the entire course.
5)
Grades will be kept by me as a percentage (%) to 2 significant figures. Grades will be
rounded (0.00–0.49 down, 0.50–0.99 up) before being entered on your transcript. Conversion of the grade percentage scores to letter grades is based on the University’s scale.
A+
> 90
A
85-89
A80-84
B+
77-79
B
73-76
B70-72
C+
65-69
C
60-64
D
50-59
F
0–49
6)
In-class quiz dates and chapter coverage are as follows: Thursday, May 19 (Chapters 13
and 14), Thursday, June 9 (Chapter 15), Thursday, June 23 (Chapter 16), Monday, July 11
(Chapter 17), Monday, July 25 (Chapters 18, 19 and 20).
7)
It has been departmental practice to post a list of laboratory and lecture marks by student
number. If you desire that your grade and student number NOT be posted, notify your
instructor. The marks are posted on the course web site, and outside the lab (Ell. 347).
8)
The date of the final examination is set by Records Services. I have no control over this
date. Students are advised not to make travel plans until their exam schedule is known.
Exceptions/exemptions based on travel plans will not be made.
Course Topics and Suggested Problems
Organic Chemistry can only be learned by actively engaging in the course material. This requires
attending the lectures, laboratories, keeping up with the readings and doing the suggested problems. Keeping current with the course material will make studying for the quizzes and exams
easier. Use the learning resources available (the lecturer, your lab section instructor, the textbook
web site, tutors, etc.). Organic Chemistry is a subject that cannot successfully be crammed the
night before the exam. It is imperative that you try as many problems as possible—the lists below
are a suggested minimum. The key to learning is to find insight and realize that certain principles
are being followed in what appear to be unrelated reactions (hint—opposites attract).
Spectroscopy is not a part of the Chemistry 232 lecture component. There will be some discussion
of spectroscopy as pertains to the laboratory, and sections pertaining to spectroscopy may be read
for interest, but no spectroscopy questions will be asked on any lecture assignment, quiz or exam.
Spectroscopy is covered in the laboratory portion, ask your TA (or me) for help as needed.
All in-chapter review problems, and the “solved problems” should be attempted and understood
as a very bare minimum. Additional end-of-chapter problems are suggested below and should be
attempted to gain a deeper understanding. You may of course do as many textbook problems as
you wish, but actually write down the answer. Don’t just say “Yeah, I know that” and move on.
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Chem 231 Review; An Overview of Organic Reactions
This section is intended as a review, no specific problems are assigned. The topics are
spread throughout the beginning of the textbook, and are fundamental to the rest of the
course. The material will not be directly quizzed.
Eleventh Edition, Solomons, Fryhle and Snyder, 2014.
Chapter 13; Allylic and Diene Systems
Covered sections: All except 13.8 (spectroscopy).
End-of-Chapter Problems: 13.20, 13.22–13.23, 13.25, 13.29, 13.30, 13.38–13.42, 13.43, 13.44.
Chapter 14; Benzene and Aromaticity
Covered sections: 14.1–14.6 & 14.7a. Read the rest of the chapter for interest!
End-of-Chapter Problems: Try 14.16–14.18 (some are difficult!), and review section 14.6.
Chapter 15; Reactions of Aromatics
Covered sections: All except 15.15 & 15.16 (read only, not examinable).
End-of-Chapter Problems: 15.22, 15.24, 15.28–15.30, 15.32, 15.36–15.37, 15.52 (challenging!).
Chapter 16; Aldehydes and Ketones
Covered sections: All except 16.3, 16.12 & 16.13 (16.3 read only, not examinable).
End-of-Chapter Problems: 16.22, 16.23, 16.26–16.31, 16.36–16.37.
Chapter 17; Carboxylic Acids and their Derivatives
Covered sections: All except 17.11 (read only, not examinable).
End-of-Chapter Problems: 17.18, 17.20–17.23, 17.28–17.30, 17.32–17.37, 17.40, 17.49–17.51.
Chapter 18; Carbonyl Alpha-Substitutions
All sections are covered.
End-of-Chapter Problems: 18.15–18.19, 18.21–18.25, 18.29 (challenging!).
Chapter 19; Carbonyl Condensation Reactions
19.4–19.6. Focus on the Aldol reaction only.
End-of-Chapter Problems: 19.33–19.34, 19.35 a–d, 19.36.
Chapter 20: Amines
Covered sections: 20.1–20.8 & 20.13.
End-of-Chapter Problems: 20.19 a–j, 20.21, 20.25 a–i, 20.31 a–f.
Chapter 22: Carbohydrates
Covered sections: 22.1–22.7, 22.10 & 22.12.
Do only the in-chapter problems.
Chapter 23: Lipids
Covered sections : 23.1–23.4E
Do only the in-chapter problems.
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Tenth Edition, Solomons, Fryhle, 2011.
Chapter 13; Allylic and Diene Systems
Covered sections: All except 13.9.
End-of-Chapter Problems: 13.17, 13.19–13.20, 13.22, 13.26, 13.27, 13.35–13.38, 13.40, 13.41.
Chapter 14; Benzene and Aromaticity
Covered sections: 14.1–14.6 & 14.7a. Read the rest of the chapter for interest.
End-of-Chapter Problems: Try 14.16 & 14.17, and review section 14.6.
Chapter 15; Reactions of Aromatics
Covered sections: All except 15.15 & 15.16 (read only, not examinable).
End-of-Chapter Problems: 15.24, 15.30–15.32, 15.34, 15.38–15.39, 15.54.
Chapter 16; Aldehydes and Ketones
Covered sections: All except 16.3 & 16.13 (16.3 read only, not examinable).
End-of-Chapter Problems: 16.19, 16.20, 16.23–16.28, 16.33–16.34.
Chapter 17; Carboxylic Acids and their Derivatives
Covered sections: All except 17.11 (read only, not examinable).
End-of-Chapter Problems: 17.18, 17.20–17.23, 17.28–17.30, 17.32–17.37, 17.40, 17.49–17.51.
Chapter 18; Carbonyl Alpha-Substitutions
All sections are covered.
End-of-Chapter Problems: 18.15–18.19, 18.21–18.25, 18.29 (challenging!).
Chapter 19; Carbonyl Condensation Reactions
19.4–19.6. Focus on the Aldol reaction only.
End-of-Chapter Problems: 19.33–19.34, 19.35 a–d, 19.36.
Chapter 20: Amines
Covered sections: 20.1–20.8 & 20.13.
End-of-Chapter Problems: 20.19 a–j, 20.21, 20.25 a–i, 20.31 a–f.
Chapter 22: Carbohydrates
Covered sections: 22.1–22.7, 22.10 & 22.12.
Do only the in-chapter problems.
Chapter 23: Lipids
Covered sections : 23.1–23.4E
Do only the in-chapter problems.
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Chemistry 232 Lecture Sequence 2016 Summer
Month
May
June
July
August
Day
2
5
9
12
16
19
23
26
30
2
6
9
13
16
20
23
27
30
4
7
11
14
18
21
25
28
1
??
2--16
Done
Introduction, Chem 231 review
Chapter 13, Allylic and Diene systems
Chapter 13, Allylic and Diene systems
Chapter 14, Benzene and Aromaticity
Chapter 15, Reactions of Aromatics, Chapter 13 & 14 review
Chapter 15, Reactions of Aromatics, QUIZ 1
Victoria Day, UVic is closed
Chapter 15, Reactions of Aromatics
Chapter 15, Reactions of Aromatics
Chapter 15, Reactions of Aromatics, Chapter 15 review
Chapter 16, Aldehydes and Ketones
QUIZ 2
Chapter 16, Aldehydes and Ketones
Chapter 16, Aldehydes and Ketones
Chapter 16, Aldehydes and Ketones, Chapter 16 review
Chapter 17, Carboxylic Acid Derivatives, QUIZ 3
Chapter 17, Carboxylic Acid Derivatives
Reading Break
Chapter 17, Carboxylic Acid Derivatives
Chapter 18, D-Carbonyl Reactions, Chapter 17 review
Chapter 18, D-Carbonyl Reactions, QUIZ 4
Chapter 18, D-Carbonyl Reactions, Chapter 19, Carbonyl Condensations
Chapter 19, Carbonyl Condensation Reactions, Ch. 18 & 19 review
Chapter 20, Amines
Chapter 22, Carbohydrates, Quiz 5
Chapter 22, Carbohydrates & Chapter 23, Lipids
BC Day
Review and Exam tutorial, before exam
Final Exam, 3 hr, sometime in that period.