Instructor:

Kamil Godula (kgodula@ucsd.edu)

office: Pacific Hall 5224A
Lecture:
M/W/F 3:00 3:50 pm, Peterson Hall 108

140C

Office Hours:
Mon 10:00 11:00 am, Pacific Hall 5224A
Tue 10:00 11:00 am, Pacific Hall 5224A
Other times available by appointment

Winter 2015

Organic Chemistry, 6th Edition

by Vollhardt and Schore

Text:

Study Guide and Solutions Manual for Organic Chemistry

Several other organic texts are available in the Science and Engineering
Library (for example: Organic Chemistry by Paula Bruice). Use them
when you desire additional reading or problems.

Teaching Assistants: Two TAs will work on this course to run Discussions sessions. They will
also hold office hours to help you with questions.
TA
Dan Honigfort
Grant Seiler

Office Hours & Place

Thu 10:00011:00am
We 12pm

York Hall 4020B

York Hall 4020B

Contact
dhonigfo@ucsd.edu
gseiler@ucsd.edu

Discussion: Teaching assistants will address key topics and problems. Homework and problemsolving strategies will be discussed. Use this opportunity to have your questions
answered and get involved in discussions.
Section
A02
A03
A04
A05
A06

Time
Mon
Mon
Mon
Wed
Wed

4:00 4:50 pm
5:00 5:50 pm
6:00 6:50 pm
8:00 8:50 am
9:00 9:50 am

Place
SOLIS 111
SOLIS 111
SOLIS 111
HSS 1128A
HSS 1128A

TA _
Dan
Dan
Dan
Grant
Grant

Chemistry 140C: Organic Chemistry

Winter 2015

Attendance and Reading: Organic Chemistry 140C is moving fast through a large amount of
lecture material. You are strongly encouraged to stay ahead of the lectures in your
reading. The Lecture will cover a selection of material from the textbook, not
necessarily in the same order as presented in the book. Attending the Lecture is a
must to succeed in the 140C class. Exams will reflect the material covered in class.
Attendance of Discussion Sections is highly recommended.
Homework:

Solving homework problems is an excellent way to study Organic Chemistry material

and to prepare for exams. The 140C course emphasizes grasp of concepts,
mechanism writing and logic over rote memorization of facts. Homework problems offer
the opportunity to practice skills in dealing with Organic Chemistry concepts.
There are two types of homework assignments in this 140C course. 1) A selection
of problems from the textbook and 2) online problem sets via the Sapling Learning
website.
1) A selection of suggested problem sets to accompany the lectures is attached to this
syllabus (p.8). These homework problems will not be turned in or graded but will be
discussed by the TAs in the Discussion Sections. Try to do as many of the suggested
practice problems as possible. Exams will be related to this homework. Doing the
homework will give you a significant advantage on the exams.
2) The Sapling Learning website will be used to assign homework for credit. See the
last page (p.9) of this Syllabus for information on signing up on the Sapling system.
Note that the homework for credit on Sapling Learning has a due date. Due dates
are listed online on Sapling and in the Course Schedule (p.3).

Examination and Grading: There will be two midterm exams and one comprehensive final
exam.
Homework on Sapling Learning
60 points
(10%)
Midterm 1
140 points
(23%)
Midterm 2
150 points
(25%)
Final
250 points
(42%)
Total
600 points
(100% of final grade)
Dates and coverage of exams are shown on the Course Schedule (p.3).
Exams will be given only at the scheduled times. Make-up exams are not given.
No exceptions. Do not ask.
Be prepared to show a picture ID at all exams. Exams will be videotaped using lecture hall cameras. If
necessary, video recordings will be used to enforce Academic Honesty investigations.
You may use either pencil or pen (black or blue; NOT red) for the exams. However, exams taken in pencil
will not be eligible for regrading. Sign every page of the exams in the top right corner. Pages which are not
signed will not be included in grading.
Notes, text books, cell phones and other electronic devices are not permitted in the exam room.
Answer keys will be posted online.

Grades breakdown is not finalized until all exams are taken.

Regrading:

Carefully check the grading on your exam after it is returned to you. Make no new marks on the exam.
Before being returned, graded exams are being copied and kept on file until after final grades are reported.
If you think that there is an error, request a regrade in writing or by e-mail to the TA, and cc e-mail to me,
within 6 days after the exam is returned. Supply the following information: your name; student id #;
problem number for which you are requesting a regrade; reason for regrading request.
When you request a regrade, the entire exam will be regraded and your score for that exam may go up or
down.
Exam score will be considered final a week (7 days) after the exams are returned to the class.

Chemistry 140C: Organic Chemistry

Winter 2015

Tentative Course Schedule* and Important Dates:

HW due*

17, 18

Jan 14

19

Jan 21

20
20

Jan 30

Date

1
2
3
4

5
7
9
12

Mon
Wed
Fri
Mon

Introduction
Review of Aldehydes & Ketones
Review of Aldehydes & Ketones
Review of Aldehydes & Ketones

14
16

Wed
Fri

Carboxylic Acids
Carboxylic Acids

19

Mon

MLK Day no class

21
23
26

Wed
Fri
Mon

Carboxylic Acids & Derivatives

Carboxylic Acids & Derivatives
Carboxylic Acids & Derivatives

28

Wed

MIDTERM EXAM 1

30
2
4

Fri (drop day)

Mon
Wed

Dicarbonyl Compounds
Dicarbonyl Compounds
Dicarbonyl Compounds

23
23

Feb 6

13
14
15

6
9
11

Fri
Mon
Wed

Amines
Amines
Amines

21

Feb 13

16

13

Fri

Heterocyclic Compounds

25

Feb 23

16

Mon

Presidents Day no classes

18

Wed

Heterocyclic Compounds

20

Fri

23
25
27

Mon
Wed
Fri

Carbohydrates
Carbohydrates
Carbohydrates

24

Mar 2

2
4
6

Mon
Wed
Fri (drop day)

Nucleic Acids
Nucleic Acids
Nucleic Acids

26
26

Mar 13

24
25

9
11

Mon
Wed

Amino Acids & Proteins

Amino Acids & Proteins

26
26

26

13

Fri

Summary

18

Wed

FINAL EXAM

Jan

5
6
7
8
9
10
11
12

Feb

17
18
19
20
21
22
23

Mar

Topic

Chapter

Lecture

MIDTERM EXAM 2

Lectures 1 9

25
Lectures 10-17

Lectures 1 26

MIDTERM 1: 3:00 3:50 pm, in class

MIDTERM 2: 3:00 3:50 pm, in class
FINAL:
3:00 pm 5:59 pm, Location to be announced
Course schedule and midterm exam dates are tentative and may change. Check for announcements
on TED.
*

HW due dates refer to the online homework on Sapling Learning (due at 11:55pm on the given date).

Chemistry 140C: Organic Chemistry

Comments and Advice:

Winter 2015

Chemistry 140C is the third and final part of a three-quarter introduction

to organic chemistry. In this part of the course the principles of organic
chemistry are expanded to illustrate their importance for real life.
Organic molecules are the basis for modern societies use of chemicals,
drugs, fuels and materials. Organic molecules and their reactions play
key roles in every aspect of biology and medicine. Chemistry 140C will
lead you into the world of amino acids, nucleotides, proteins and nucleic
acids, the very basis of life. Knowledge of organic chemistry provides
you with insight literally into the heart of things and beings.
Like a language, organic chemistry is a complex of words (facts) and
grammar (principles and mechanisms). Without an understanding of the
grammar the memorization of words alone will not allow you to speak a
language. While certain facts have to be learned and recognized,
the understanding of fundamental principles and mechanisms is
essential
to
successfully
studying
organic
chemistry.
Memorization is not the right way to study organic chemistry.
Medical schools view organic chemistry grades as important, not
because they select for people who can memorize, but because they
seek people who can abstract fundamental principles from a large body
of facts and extrapolate to novel situations.
Read the text book chapters in advance and do as many exercises
and problems as you can. Organic chemistry classes are dense and
fast moving. In every lecture new conceptual material needs to be
assimilated that will be the basis for the next topic of the following
lecture. It is important to continuously learn and practice all covered
topics. Do not fall behind. Solving problems is the best way to exercise
and test your understanding of new concepts. Although they will not be
graded, the assigned homework is your best choice to test your
knowledge.
Take notes during lecture. Writing things down is critical for learning
organic chemistry. It is not sufficient to read and look at drawings.
Practice the writing of reactions and their mechanisms (electron
pushing). Take the time to draw all steps yourself.
Study in small groups. Get together with a group of students from the
class to work out the homework problems and discuss the material.
Cooperation on problem solving is encouraged.
Seek help and advice from the instructors. Do not hesitate to come
to office hours. The TAs and I have set time aside to help you with
problems during your organic chemistry studies. When you encounter a
problem and your own attempts to solve it fail, ask us.
The success of education depends on the ethical behavior of all
participants in an open learning environment. Do not get involved in
cheating or plagiarism. If you have a problem of any sort that influences
your performance, come and see your instructor.

Chemistry 140C: Organic Chemistry

Winter 2015

A Note about the Internet: Wikipedia articles (and the like) can be important sources of information
that are readily accessible and often contain useful compilations of
material. I encourage the use of it. However, keep in mind that
information in Wikipedia (and other places on the internet) is collected
through an open source mechanism that sometimes lacks rigorous fact
checking. If you find information on an internet web page contradicting
the course text book, I advise not dismissing the book right away. Text
books such as the one used for this course have been around for a
while and can be considered reliable sources of information. You can
bring up such discrepancies in office hours or discussion sections but,
please, do not argue with me that the mechanism you wrote in an exam
must be correct because you saw it somewhere on the internet.

Academic Honesty:

I encourage you to study together. However, copying, discussing

material or using reference material, written, printed, or from electronic
sources, during an examination is cheating. Any student found cheating
on an exam will receive a 0 on that exam. A letter explaining the
reasons for this grade will be sent to the appropriate University officials
for disciplinary action. Taking an examination for someone else or
having someone else take an examination for you is a very serious
offense for which expulsion from the University will be urged. Changing
an answer on an exam that has been returned to you and then
requesting a regrade is a serious offense. Remember that you may
not drop or withdraw from a course while a dishonesty case is pending,
or if found guilty.

OSD Accommodations:

If you have been given an Authorization for Accommodation (AFA)

letter from the Office of Students with Disabilities (OSD), you must
provide the instructor, your TA, and the OSD Chemistry Department
Liaison with a copy of the letter before any accommodations will be
provided. You and the instructor will coordinate all exam scheduling,
with involvement from the OSD Liaison as needed. In order to
guarantee accommodations, you must follow the guidelines established
by the Instructor and/or Liaison. OSD exams will run concurrently
with the scheduled exam.

Chemistry 140C: Organic Chemistry

Fall 2013

Study Guide for the Vollhardt Textbook:

Listed below are key topics for each chapter to help you focus your studies.
condensed list. Additional topics will be covered in class.

This is a

Chapters 17, 18 Aldehydes and Ketones/Enols and Enolates

As seen in 140B/BH, an aldehyde contains a carbonyl group (C=O) connected to a hydrogen
atom and a carbon atom. A ketone contains a carbonyl group (C=O) connected to two carbon
atoms. Important topics to understand include: (a) the electronic features of the carbonyl group
in relation to its physical properties and reactivity, (b) major synthetic ways to make aldehydes
and ketones, (c) major reactions of aldehydes and ketones, particularly addition of nucleophiles
to the electrophilic carbon.
Note that while in Ch. 16 you, for the most part, worked on reactions at the carbon of the
carbonyl group, in Ch. 18 you will be dealing with the reactivity of the carbon next to the
carbonyl functionality. An enolate ion is an anion generated by the removal of an -hydrogen
from a carbonyl-containing compound. Aldehydes and ketones (as well as esters, as we will
see later) can be converted into their enolate anions by treatment with very strong bases.
Enolates are typically considered to be rather reactive intermediates (and in most cases are
generated from the corresponding carbonyl compounds just prior to their reactions with other
electrophiles). An enol is a tautomeric form of a carbonyl compound. Important issues to
cover: (a) tautomerism, (b) factors influencing the acidity of carbon acids, (c) mechanisms of
enol and enolate formation, (d) reactions of enolates with simple electrophiles (e.g., alkyl
halides), (e) reactions of enolates with other carbonyl compounds; the aldol reaction, (f)
reactions of enolates with ,-unsaturated carbonyl compounds, conjugate (1,4) additions, the
Michael reaction.
Chapters 19, 20 Carboxylic Acids and their Derivatives
The functional group of a carboxylic acid is the carboxyl group CO2H. Important topics to
understand include: (a) the electronic features of the carboxyl group in relation to its acidity,
basicity, involvement in hydrogen bonding and reactivity, (b) the electronic features of the
various carboxyl acids derivatives (acyl halides, anhydrides, esters, amides, nitriles) in relation
to their physical properties and reactivity, (c) major synthetic transformations of carboxylic acids
and their derivatives, (d) fundamental mechanistic aspects of additionelimination reactions.
Understanding the relative reactivity of the various derivatives (i.e., halides, anhydrides, esters
and amides) is crucial! Familiarize yourself with the interconversion of the various derivatives
(e.g., anhydrides to esters, esters to amides, etc.).
Chapter 23 Dicarbonyl Derivatives and their Reactions
Study the mechanisms of the Claisen condensations and retro-Claisen reaction. When does
the Claisen condensation fail? Dicarbonyl compounds are important synthetic intermediates.
Follow the mechanisms involved. Study the mechanism and use of the decarboxylation of 3keto-acids (reactions of stabilized anions derived from dicarbonyl compounds such as ethyl
malonate with electrophiles, followed by decarboxylation, are very useful for synthesizing

Chemistry 140C: Organic Chemistry

Fall 2013

functionalized ketones and carboxylic acids). Important issues to cover: (a) acidity of
dicarbonyl compounds, (b) reactions of stabilized enolates, (c) the mechanism of
decarboxylation reactions.
Chapters 21, 25 Amines and Heterocycles
Amines are derivatives of ammonia (NH3) in which one or more hydrogens are replaced by alkyl
or aryl groups. Important topics to learn include: (a) the electronic features of amines in
relation to their acidity, basicity, involvement in hydrogen bonding and reactivity, (b) the
classification of amines to primary (1), secondary (2), tertiary (3) and quaternary (4), (c)
major methods of synthesizing amines, (d) major reactions of amines. We will need to
remember their physical properties and reactivity patterns when we will learn about amino acids.
A heterocyclic compound is one that contains more than one kind of atom in a ring. In organic
chemistry we refer to a ring in which one or more of the atoms is other than carbon (typically N,
O, S, etc.). We will focus on simple N-containing heterocycles with significance to biomolecules
(particularly amino acids and nucleic acids).
Chapter 24 Carbohydrates
Carbohydrate chemistry is rather complex. Fundamentally, however, it is related to the
chemistry of the functional groups found in sugars (another name for carbohydrates): OH and
>C=O.
Important issues to pay attention to include: (a) stereochemical aspects
(carbohydrates contain numerous chiral centers); review Fischer projections if needed, (b) open
and cyclic forms; understand the formation of cyclic hemiacetals and the possible
interconversions between the various forms, (c) reactions of carbohydrates as alcohols and
carbonyl derivatives, (d) how to distinguish between reducing and non-reducing sugars, (e) the
formation of glycosides and oligosaccharides.
Chapter 26 Amino Acids and Proteins
The building blocks of peptides and proteins are -amino acids (at least in human biology). You
may need to review the chemistry of carboxylic acids and the chemistry of amines. Important
aspects: (a) acid-base properties (amino acids are amphoteric), (b) the structure and formation
of the peptide (amide) bond, (c) primary, secondary, tertiary and quaternary structures of
proteins.
Chapter 26 - Nucleic Acids
The chemistry of nucleic acids brings together heterocycle chemistry with carbohydrate
chemistry. Some of this chemistry is discussed in Ch. 25.2 and 25.3. Important issues: (a)
learn to recognize the various nucleosides and their substructures, (b) base pair formation by
hydrogen bonding, (b) distinguish between a nucleoside and a nucleotide, (c) DNA structure:
the covalent backbone and the DNA double helix, (d) the chemical difference between DNA and
RNA.

Chemistry 140C: Organic Chemistry

Recommended Reading:

Fall 2013

The following chapter sections of the Vollhardt text book, 6th

Edition, are required reading to prepare in advance of the
lectures. I strongly recommend reading other sections as well.
Ch. 17:
Ch. 18:
Ch. 19:
Ch. 20:
Ch. 23:
Ch. 21:
Ch. 25:
Ch. 24:
Ch. 26:

Homework Assignment:

17-2, 17-5 17-7, 17-9, 17-11, 17-14

18-1 18-11
19-1 19-4, 19-6 19-11, 19-13
20-1 20-8
23-1 23-3
21-1 21-10
25-1 25-5, 25-8
24-1 24-4, 24-6, 24-8 24-12
26-1 26-6, 26-9 26-11

The following Exercises from within the text and Problems, 6th
Edition, are assignments as homework for the Discussion
sections.

Exercises (within each chapter)

Ch. 17

13-16

18

Ch. 18

1-4

7-9

13-20

22

Ch. 19

5-8

11

14

17-20

Ch. 20

Ch. 23

1-21

Ch. 21

9-12

Ch. 25

Ch. 24
Ch. 26

24

28-29

9-11

13-15

14-16

21

24

9-11

14

3-7

14

17

19

20

9-11

24

17-19

21

27

29

30a

31ac

Problems (at the end of each chapter)

Ch. 17

33-38

41ab

59

Ch. 18

32-34

37-38

42-45

47

49

56

57

58ab

Ch. 19

29-30

33

39

40a-d

46

49

51

55

Ch. 20

32

34-36

38-39

41-43

45-46

49

51

53-54

56-57

59-60

Ch. 23

27-30

32-37

40

Ch. 21

34

35

37

39abdh, j

41-46

48

49a

53

56

59

Ch. 25

32ac

33

35-38

41

44

45

Ch. 24

33

34

38-40

43

45

46

53-56

60

Ch. 26

30-33

36-38

42-44

57

63

Chemistry 140C: Organic Chemistry

Fall 2013

Information on the Sapling Learning website:

Homework problems that accompany the 140C lecture will be assigned through the Sapling
Learning website. Up to 60 points, corresponding to 10% of the final grade, may be achieved by
correctly solving the online homework.
Sapling's chemistry questions are delivered in a web browser to provide real-time grading,
response-specific coaching, improvement of problem-solving skills, and detailed answer
explanations. Dynamic answer modules enable one to interact with 3D models and figures,
utilize drag-and-drop synthetic routes, and draw chemical structures - including stereochemistry
and curved arrows.
Signing up for Sapling Learning is required for this course. The fee is $22.50
To get started:
1. Go to http://saplinglearning.com
2a. If you already have a Sapling Learning account, log in and skip to step 3.
2b. If you have Facebook account, you can use it to quickly create a Sapling Learning account.
Click the blue button with the Facebook symbol on it (just to the left of the username field). The
form will auto-fill with information from your Facebook account (you may need to log into
Facebook in the popup window first). Choose a password and timezone, accept the site policy
agreement, and click "Create my new account". You can then skip to step 3.
2c. Otherwise, click "create account. Supply the requested information and click "Create my
new account". Check your email (and spam filter) for a message from Sapling Learning and
click on the link provided in that email.
3. Find your course in the list (you may need to expand the subject and term categories) and
click the link.
4. Select a payment option and follow the remaining instructions.
5. Work on the Sapling Learning training materials. The activities, videos, and information pages
will familiarize you with the Sapling Learning user environment and serve as tutorials for
efficiently drawing molecules, stereochemistry, etc. within the Sapling Learning answer
modules. These training materials are already accessible in your Sapling Learning course.
Once you have registered and enrolled, you can log in at any time to complete or review your
homework assignments. During sign up - and throughout the term - if you have any
technical problems or grading issues, send an email to support@saplinglearning.com
explaining the issue. The Sapling support team is faster to resolve issues than your
instructor.
(This information, including the link to Sapling, is also available online on TED)