Chem 360 Stu Man 554275

Chemistry 360
Organic Chemistry II
Student Manual
Note: The Student Manual was prepared primarily for individualized-study

students. Students who are taking this course with seminar support or
through a co-operating institution should be aware that some of the
information will not apply in their situation. In case of doubt, please ask
your tutor or seminar leader about any problems that might arise. Further
clarification can be obtained from the course professor.
Athabasca University
Course Team
Course Professor: Lawton Shaw
Course Authors: Arthur Last and Dietmar Kennepohl
Revisions: Dietmar Kennpohl (1996-2004); Lois Browne (2010)
Reviewer, 2004: David Law
Editor: Gilda Sanders
Visual Presentation: Athabasca University Digital Media Technology Unit
Cover Design: Jingfen Zhang
Note: This course is a revision of a part of Chemistry 345: Organic Chemistry

c 1991 by Athabasca University.
by Arthur Last, copyright
Every effort has been taken to ensure that these materials comply with the
requirements of copyright clearances and appropriate credits. Athabasca
University will attempt to incorporate in future printings any corrections
which are communicated to it.
The inclusion of any material in this publication is strictly in accord with the
consents obtained and Athabasca University does not authorize or license
any further reproduction or use without the consent of the copyright holder.
c Athabasca University 1998, 2003, 2004, 2010
All rights reserved

Printed in Canada
CMID 554275
Revision 6
Contents
The Course . . . . . . . . . . . . . . . . . . . . . . .
The MyAU Portal . . . . . . . . . . . . . . . . . . .
Your Student ID Number . . . . . . . . . . . . . . .
Freedom of Information and Protection of Privacy
The Athabasca University Calendar . . . . . . . .
Course Materials . . . . . . . . . . . . . . . . . . .
Other Items . . . . . . . . . . . . . . . . . . . . . .
Forms . . . . . . . . . . . . . . . . . . . . . . . . . .
Course Design . . . . . . . . . . . . . . . . . . . . .
Laboratories . . . . . . . . . . . . . . . . . . . . . .
Your Tutor . . . . . . . . . . . . . . . . . . . . . . .
The Course Professor . . . . . . . . . . . . . . . . .
Services to Students . . . . . . . . . . . . . . . . . .
Library Services . . . . . . . . . . . . . . . . . . . .
Study Strategies . . . . . . . . . . . . . . . . . . . .
How to Use the Study Guide . . . . . . . . . . . .
Course Outline and Study Schedule . . . . . . . .
Assessment . . . . . . . . . . . . . . . . . . . . . .
Applying for and Writing Examinations . . . . . .
Student Conduct and Appeals . . . . . . . . . . . .
Intellectual Indebtedness . . . . . . . . . . . . . . .
Transcripts . . . . . . . . . . . . . . . . . . . . . . .
Transferring Credit . . . . . . . . . . . . . . . . . .
Applying for Extensions . . . . . . . . . . . . . . .
Sample Examinations . . . . . . . . . . . . . . . . .
Sample Examination Answer Keys . . . . . . . . .
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55
The Course
Welcome to Chemistry 360: Organic Chemistry II, a three-credit, senior-level,
laboratory science course. We assume that all students registering in this
course will have completed Athabasca Universitys Chemistry 350: Organic
Chemistry I, or an equivalent university-level course in organic chemistry. If
you have not done so, you should contact the course professor immediately.
Organic Chemistry II deals with the chemistry of carbon compounds through
a study of the characteristic reactions of the common functional groups.
Particular emphasis is placed on the study of reaction mechanisms, in an
attempt to show similarities between apparently unrelated reactions. The
importance of stereochemistry is stressed throughout the course. The
compulsory laboratory component of Chemistry 360 introduces the student
to the basic techniques employed in modern organic chemistry laboratories.
Experiments have been selected to illustrate many of the principles
encountered in the theoretical part of the course. The course outline
provided in this manual gives a more detailed description of the course
contents.
This Student Manual provides you with some essential information about
the design of the course, the course materials, and the procedures you
should follow to obtain the maximum benefit from your studies. Please read
it carefully and keep it in a safe place.
Note: These course materials have been designed for students who are
taking the individualized-study version of this course. Students who are in
a grouped-study environment should follow the course outline, study
schedule and learning activities provided by their instructor.
The MyAU Portal

MyAU is a personalized portal to Athabasca University where you can
quickly access information that is relevant to you. Through myAU, you can
view personal information, such as library accounts and assignment marks
and course grades, and take care of administrative matters, such as booking
examinations, submitting assignments, applying for extensions, registering
for courses and so on. Athabasca University will also communicate directly
with you through myAU. Check the Message Centre on your myAU home
page for general information and for mail addressed specifically to you.
To login at
http://my.athabascau.ca/
enter your student ID number and password where requested. If you are
having browser difficulties or you need help, refer to myAU Help at
http://www.athabascau.ca/uportal/help/index.php
Your Student ID Number

In contacts with your tutor, on assignments, or in any correspondence or
other contact with the University, you are asked to provide your student ID
number. Record this number in the space below. Having your student ID
number will help University personnel to process requests, grades and
administrative matters more quickly.
Student ID number:
Note: It is important that we receive notification of any change of address or
telephone number. Please inform the Office of the Registrar whenever such
a change occurs. You can do so through your myAU portal, or you can use a
student change of information form (see the section of this manual titled
Forms). In addition, you should send change-of-address cards to your
tutor and to the course professor, so that your student files can be kept
up-to-date.
Freedom of Information and Protection of Privacy

The personal information and records collected and maintained by the
University as a result of a students registration in this course, such as
completed assignments and examinations, electronic communications and
correspondence, are subject to University policies and the privacy and
access provisions of the Alberta Freedom of Information and Protection of
Privacy Act.
The Athabasca University Calendar

Because Athabasca Universitys policies, practices, and procedures change
over time, some of the information in this Student Manual may lose its
currency between course revisions. Students are therefore advised to refer
to the current Athabasca University Calendar on important issues concerning
University policies, procedures and practices. In the event of any
discrepancy between the printed version of the Calendar and the official
web-based Calendar, the web-based version will be binding.
Chemistry 360 / Student Manual
Course Materials
The package you received should include each of the items listed below. If
anything is missing from your package, please contact the Course Materials
division of Athabasca University as soon as possible. If you live in Canada
or the United States, you can use email to contact Course Materials:
cmat@athabascau.ca
You can also call 1-800-788-9041, choose option 3 from the menu, and enter
extension 6366 when prompted.
Students who live outside of Canada or the United States can contact
Course Materials by email.
You can also write in care of Course Materials, Tim Byrne Centre, 400 Hwy 2
South, Athabasca, AB T9S 1A4.
Textbooks
McMurry, John. Organic Chemistry, 7th ed. Pacific Grove, CA: Brooks/Cole
Publishing Co., 2008.
McMurry, Susan. Study Guide and Student Solutions Manual for McMurrys
Organic Chemistry, 7th ed. Pacific Grove, CA: Brooks/Cole Publishing
Co., 2008.
Athabasca University Materials

Chemistry 360: Organic Chemistry II. Student Manual. Athabasca, AB:
Athabasca University, 2010.
You are now reading the Student Manual.
Chemistry 360: Organic Chemistry II. Study Guide. Athabasca, AB: Athabasca
University, 2010.
The Study Guide, as its name implies, is designed to guide your study of
the course textbook.
Chemistry 360: Organic Chemistry II. Assignment Manual. Athabasca, AB:
The Assignment Manual contains the self tests and answers to the self
tests, as well as the two tutor-marked assignments.
Chemistry 360: Organic Chemistry II. Laboratory Manual. Athabasca, AB:
Other Items
The items listed below are not supplied; you should purchase them before
you begin to work on the course. You will need
an electronic calculator capable of handling logarithms and exponentials.
Remember: Take your calculator with you whenever you write an

examination or attend a laboratory session.
a lab coat. You will not be allowed to attend lab sessions without one.
a laboratory notebook.
other stationery, including paper for assignments, pens, pencils, a
ruler, etc.
Forms
The forms you need to submit assignments, request examinations or inform
the University of a change in your status as a student are available through
your myAU home page, or for download from the Office of the Registrars
Online Services (OROS) website:
http://www.athabascau.ca/registrar/forms.php
If you do not have access to the Internet or are unable to obtain the forms
online, please contact the Athabasca University Information Centre, toll
free, at 1.800.788.9041 to request that printed copies be sent to you. For
Chemistry 360, you will need at least two tutor-marked exercise forms and
two examination request forms.
Course Design
The course materials are designed for self-instruction and individualizedstudy. What you should learn and how you should learn it are described in
the Study Guide. This book contains 16 units, each of which corresponds to
one of the chapters in Organic Chemistry, 7th ed., by John McMurry. Each
unit in the Study Guide contains a preview, a list of learning objectives, a
series of subsections corresponding to chapter subsections, and some hints
on how to work through the unit. Let us look at exactly what you can expect
to find under each of these headings.
Unit Preview
The Unit Preview is a brief discussion that outlines the overall approach
taken by the author in the relevant chapter of Organic Chemistry.
Unit Objectives
In this section, we inform you of the overall objectives that we expect you to
be able to fulfill when you have finished studying the unit.
Sections
The sections form the bulk of each unit. Each section in the Study Guide
normally contains the following features:
1. a list of objectives which are more detailed than those provided under
the heading Unit Objectives, and which may be one of the most
valuable features of the Study Guide, because they tell you explicitly what
you need to understand and to be able to do for each unit of the course.
Questions on the examinations and tutor-marked assignments are based
only on the unit objectives. However, you should be aware that many
questions will require you to demonstrate mastery of a number of related
objectives, and that you should not place too narrow an interpretation on
each objective.
2. a list of key terms introduced in the section. Unless we have indicated
otherwise, definitions of these key terms are provided in Appendix
CGlossary, beginning on page A10 of Organic Chemistry, 7th ed.
3. study notes, which may include hints on how to study the material
effectively, additional information, and details of any errors that occur in
the textbook.
4. a list of suggested exercises. These exercises are designed to improve
your understanding of the material you have just studied and to develop
your problem-solving skills. Refer to your notes and to the textbook
when you attempt the exercises. The answers to all the exercises are
provided in the Solutions Manual or in Appendix DAnswers to In-text
Problems, beginning on page A30 of the textbook. Do not spend a large
amount of time on any one exercise. If you are unable to make any
progress after a few minutes of concentrated work, use the answers
to help.
For further information, see the section of this manual titled How to Use
Your Study Guide.
Self tests are given at the end of Units 18, 20, 22 and 24, and after each of the
optional units. These tests are designed to allow you to measure your
progress in the coursethey are not a comprehensive overview of the
material, nor are they at the same level of difficulty that you will encounter
in the midterm and final examinations. [Sample examinations are given in
this manual.] If you have difficulty with any self test, you should go back
and review the material before going on.
The textbook by McMurry contains most of the information you will need
to pass this course. It is a standard textbook used in many universities and
colleges throughout North America. It was chosen because it offers clear
explanations and interesting discussions of the material we wished this
course to cover. In addition, we felt that this textbook has an advantage in
that it includes some discussion of a number of advances made in organic
chemistry during the last decade. The chapters are relatively short, and the
textbook contains problems, exercises and some review chapters.
Each chapter of the textbook concludes with a useful summary, and where
appropriate, a list of the reactions introduced in the chapter. These reviews
are excellent for quick reference and will help you to prepare for
examinations.
You should use a set of molecular models to assist you in understanding the
stereochemical aspects of the course. If you cannot obtain a set of molecular
models elsewhere, you may order one from the Athabasca University
Library (see the section of this manual titled Library Services). You may
use molecular models during examinations.
Laboratories
You must complete about 32 hours of laboratory work to obtain credit in
this course. Labs are typically held for week-long sessions during the
summer in Athabasca, or for full-day sessions on weekends in Edmonton at
selected times during the rest of the year. The Lab Coordinator will be able
to provide up-to-date information, or you may go to our Lab Information
website at:
http://science.pc.athabascau.ca/labinfo.nsf
You must contact the Lab Coordinator to book into a scheduled laboratory
session. Students in Canada and the United States can reach the Lab
Coordinator by calling 1-800-788-9041 (the extension is 6276). All students
can use electronic mail to contact the Lab Coordinator at
sciencelab@athabascau.ca
Information about the laboratory program and the experiments to be
carried out is included in the Laboratory Manual. Note that your lab work
accounts for 20 per cent of your overall course mark. You must satisfactorily
complete and write up a specified minimum number of experiments to
obtain credit for this course.
Your Tutor
Athabasca University provides each student in each course with a tutor
whose responsibility is to help the student complete the course successfully.
A letter containing your tutors name, address, telephone number and
tutoring hours was mailed to you shortly before your official start date. If
you have not yet received your tutor letter, please contact Learning
ServicesTutorial at Athabasca University as soon as possible. Students in
Canada or the United States can call 1-800-788-9041 (extension 6196); all
students can send electronic mail to
tutserv@athabascau.ca
Note: If you have chosen to receive communications from Athabasca
University in electronic form, be sure to check your myAU portal for your
tutor letter.
Your tutor has excellent academic qualifications, and is committed to
helping students learning at a distance. He or she is available to answer
your questions about course content or how to approach a problem or an
assignment, and can direct you to the right person or department to help
you with other problems that may be hindering your progress in your
course or program. In addition, your tutor will be responsible for marking
your assignments. In general, you should call your tutor first with any
queries about Athabasca University.
The tutor letter will help you become acquainted with your tutor and will
provide information about your tutors schedule. If you have not yet
received a call from your tutor, do not hesitate to make the first call yourself.
If you live in Canada or the United States, you can call your tutor, toll free,
during his or her tutoring hours, using the information provided in the
tutor letter. If you live outside of Canada or the United States, please refer to
the tutor letter and the current Athabasca University Calendar for information
about calling your tutor.
We suggest that you contact your tutor as soon as you receive the course
materials, and then get into the habit of communicating regularly, when you
complete a unit or when you run into any special problem. We have found
that students who maintain regular contact with their tutors are most likely
to be successful in completing their courses, so do keep in touch. You may
find it useful to schedule a regular study period when your tutor is
available so that you can contact him or her when questions arise. If you are
unable to take advantage of the regular tutoring hours, contact your tutor or
the course professor to determine whether alternative arrangements can be
made.
If you use postal mail to send an assignment to your tutor, be sure to attach
a tutor-marked exercise form, and to keep a copy, at least a rough draft, in
case the original goes astray in the mail. If you take this course through the
Moodle course management system, you may be instructed to use the
Assignment Drop Box to submit your assignments. If you wish to submit
your assignments electronically outside of the Moodle system, contact your
tutor to discuss appropriate formats. An electronic version of the

tutor-marked exercise form is available online through your myAU portal.
In any case, allow several working days, in addition to mailing time each
way if applicable, before you expect to receive the graded assignment. Your
tutor will be pleased to provide additional feedback. Be sure to mention any
questions you have about the assignment or the grade.
Keep your tutors letter of introduction with your course materials, and use
the space below to record information about your tutor.
Tutors name:
Address:
Telephone number:
Electronic mail address:
Tutoring hours:
Note: If we are to keep you informed of upcoming laboratory sessions, etc.,
it is important that we receive notification of any change of address or
telephone number. Please inform the Office of the Registrar whenever such
a change occurs.
The Course Professor

The course professor is the member of Athabasca Universitys academic
staff who is in charge of a given course. The professor works directly with
tutors on both academic and administrative matters. If you have difficulties
you cannot resolve with your tutor, you may wish to speak with the
professor directly. You should also address any questions about credit
records or centrally marked examinations to the professor. The professor
can also provide general information about program planning and
curriculum development. The course professor welcomes students
comments on the course.
Services to Students
Athabasca University offers a wide range of services to its students. The
Athabasca University Information Centre (1.800.788.9041) can help you find
the answer to most administrative questions. The Centre is staffed on
regular business days from 7:00 a.m. to 5:30 p.m., Mountain Time.
Advisors are available to assist students in planning their programs and
selecting appropriate courses. Counselors assist students in improving their
study skills and clarifying their educational goals. You may reach an
advisor or counselor in several ways: by dialling 1.800.788.9041 and asking
to speak with an advisor or counselor; by visiting Athabasca Universitys
Central Office in Athabasca, or the Athabasca University sites in Edmonton
or Calgary; or by directing your query to
http://www.askau.ca
Students who are looking for information about student awards and advice
about obtaining financial assistance are asked to contact the Office of the
Registrar. You may do so by dialling 1.800.788.9041 and asking for the Office
of the Registrar, or by inquiring through
http://www.askau.ca
Note: Students may write examinations at the Athabasca University sites in
Athabasca, Edmonton or Calgary, or at the other locations listed online at
http://www.athabascau.ca/registrar/invignet.php
At the Athabasca University sites in Athabasca, Edmonton or Calgary,
students can also order materials from the Library, and take care of various
administrative matters, such as course registration and arrangements for
extensions.
Indigenous Services at Athabasca University

If you are a student of Indigenous ancestry (Aboriginal, First Nations,
Indian, Inuit, Native, Mtis), or a non-Indigenous student who is interested
in identifying culturally appropriate services designed for Aboriginal
students or counseling that is sensitive to the challenges Aboriginal
students face, please contact the Centre for World Indigenous Knowledge
and Research, by telephone at 1.800.788.9041, extension 2064, or by
electronic mail at
indigenous@athabascau.ca
Library Services
The Athabasca University Library collection contains more than 140,000
books, many periodical titles and a range of audio-visual resources. The
Library subscribes to over 100 online databases, providing full text access to
selected articles from more than 20,000 journals.
Athabasca University Librarys collection primarily supports Athabasca
University courses and programs. Materials found in the print and
electronic collections are available for use by our students, faculty and staff
for reference and research purposes. Requests for library materials or
services can be made, by email, phone, fax or mail, 24 hours a day (contact
information is provided below). Responses to most requests are handled
within 24 hours, or by the next business day. Borrowed materials are
normally mailed to the students home address, along with a returnmail card.
Core Services to Students

Athabasca University students registered in a course may
borrow library materials.
search the Librarys online catalogue (AUCAT).
access resources through the Librarys website.
receive library instruction and research assistance.
request interlibrary loan (ILL) services for journal articles and
book chapters.
Digital Resources
Access to online journal databases, the Digital Reference Centre (DRC), and
the Digital Reading Room (DRR) is available from Athabasca University
Librarys main web page
http://library.athabascau.ca
Tips on searching the journal databases and help with researching, writing
and citing (referencing) can be found in the Help Centre
http://library.athabascau.ca/help.php
Supplementary Materials
University courses often require that students investigate material beyond
the contents of the course materials package. Some Athabasca University
course Study Guides list Supplementary Materials, including books,
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journal articles or audio-visual materials, which students may find useful

when completing assignments and course projects. The supplementary
materials referenced in your course materials package are usually available
from the Athabasca University Library or your local library. Contact the
Athabasca University Library to request materials.
How the Library Gateway Works

The Library website contains the Librarys online catalogue (AUCAT), and it
is also the gateway to other online information. The website provides links
to journal databases and other subscribed online resources, as well as to
selected, publicly accessible Internet sites. Subscribed resources are
available to Athabasca University students, faculty and staff. You will be
required to enter your first and last names as your username and your
student ID number as your password.
The Library website also provides access to selected library catalogues from
Canadian public and academic libraries.
Interlibrary Loans
An interlibrary loan (ILL) involves one library borrowing materials from
another on behalf of a library user. Athabasca University Library will
request photocopies of journal articles and book chapters through
Interlibrary Loans, if you provide the Library staff with a complete
bibliographic citation (author, title of article, name of journal, volume and
issue number, year of publication, and page numbers) for the requested
item. You are not required to return these items to us. Allow sufficient time
for the material to be ordered and received. More information on the
Interlibrary Loan process is available on the Library website at
http://aupac.lib.athabascau.ca/screens/ill.html
Contacts
Athabasca University Library
1 University Drive
Athabasca, AB Canada T9S 3A3
Library website: http://library.athabascau.ca
E-mail: library@athabascau.ca
Phone: 1.800.788.9041 (ext. 6254) Canada/US
Fax: 780.675.6477
11
Study Strategies
Chemistry 360 is a three-credit course and must be completed within the six
months of your contract period. This may seem like a long time, but
procrastination can rapidly put you in a difficult position. We suggest you
start right away and that you establish a study schedule. Your tutor can
help you.
How fast you proceed through the first few units will depend on your
background in organic chemistry from Chemistry 350. If your background is
weak, you may have to put in extra time, and this may affect your chances
of completing the course within the normal six-month contract period. If
you find that you really have trouble with Units 17 and 18, you should
discuss the situation with your tutor and consider withdrawing from the
course or taking some action to improve your understanding of
fundamental organic chemistry.
At a traditional university, this course would normally be spread over one
semester and take about 12-13 weeks to complete. If you wish to attain this
rate, follow the 13-week study schedule shown in the Course Outline and
Study Schedules section of this Student Manual. If you wish to proceed at
somewhat slower rate, refer to the 18- and 24-week schedules when you
plan your own personal study schedule. Remember that regular study
habits can be a major contributing factor to ultimate success in this course.
Should unforeseen circumstances put you in a position where you find that
you cannot complete the course within six months, check the Athabasca
University Calendar for current regulations about extensions.
Although the amount of time that a student will need to spend on the
course will depend on a variety of factors, students intending to complete
the course in 13 weeks should be prepared to spend at least nine (9) hours
per week on the course. You may need additional time when you have
laboratory reports to write, or when you are reviewing for an examination.
We suggest that you start Unit 17 now. As you work through it, make a note
of any questions you have on content, study procedures, etc. Then, before
you go on to the next unit, contact your tutor to clear up these questions.
How to Use the Study Guide

As you study each unit in Chemistry 360, follow the procedure outlined
below.
1. Read the preview and the list of unit objectives at the beginning of the
unit. At this stage, some students find it beneficial to obtain an overall
picture of the unit by quickly reading through the whole chapter in the
textbook.
12
2. Study each lesson in the unit by

a. reading the objectives and study notes (if any). These notes may
contain study hints or additional information, and will also identify
any errors that occur in the relevant section of the textbook.
b. reading the required pages in the textbook and using the objectives
and key terms to guide you in making your own notes.
c. completing the assigned exercises and checking your answers in the
Study Guide and the textbook. Note that your problem-solving ability
will largely determine the overall grade that you receive in this course.
3. Review the unit by
a. making sure that you understand each of the unit objectives and can
do what they require.
b. making sure that you can define and use the key terms.
c. reading the summary and the summary of reactions (where
appropriate) given at the end of the chapter in the textbook.
d. completing a selection of the recommended exercises listed in the
Study Guide.
4. Do the tutor-marked assignment (if there is one) and send it to your
tutor, or do the self test (if there is one) and check your own progress.
Warning: One of the problems with distance education is that, occasionally,
lab reports, assignments, etc., get lost in the mail. As we can only give credit
for work that is actually received, we strongly advise that you keep a rough
copy of all of the work that you submit to your tutor by mail. Also, please
make certain that you attach a Tutor-marked Exercise form to any work
you mail in for grading. Student using the Moodle Assignment Drop Box
should follow the instructions given on the Moodle course website.
13
Course Outline and Study Schedules

The table below gives a brief course outline and suggests the amount of
time students should spend on each unit for 13-, 18- and 24-week schedules.
Note: Students who are receiving financial assistance may face special time
constraints. Please check your course registration for any restrictions on the
length of registration, and be prepared to adjust your schedule.
Unit number and title
13-week
schedule
18-week
schedule
24-week
schedule
17
Alcohols and Phenols
Week 1
Week 1
Weeks 1-2
18
Ethers and Epoxides;

Thiols, and Sulphides
Week 2
Week 2
Weeks 3-4
A Preview of Carbonyl
Compounds
Aldehydes and Ketones:
Nucleophilic Addition
Reactions
Carboxylic Acids and
Nitriles
Carboxylic Acid
Derivatives and
Nucleophilic Acyl
Substitution Reactions
Carbonyl
Alpha-Substitution
Reactions
Week 2
Week 2
Week 5
Week 3
Weeks 3-4
Weeks 6-7
Week 4
Week 5
Week 8
Week 5
Weeks 6-7
Weeks 9-10
Week 6
Week 8
Week 11
Review for Midterm

Examination
Carbonyl Condensation
Reactions
Amines and Heterocycles
Week 7
Week 9
Week 12
Week 8
Weeks 10-11
Weeks 13-15
Week 10
Weeks 12-13
Weeks 16-18
19
20
21
22
23
24
14
25
Biomolecules:
Carbohydrates
Week 11
Weeks 14-15
Weeks 19-21
26
Week 12
Weeks 16-17
Weeks 22-23
27
Biomolecules: Amino
Acids, Peptides, and
Proteins
Biomolecules: Lipids
Week 12
Weeks 16-17
Weeks 22-23
28
Biomolecules: Nucleic Acids
Week 12
Weeks 16-17
Weeks 22-23
Review for Final

Examination
Week 13
Week 18
Week 24
The table below allows you to plan (with the help of your tutor) a
personalized study schedule. We suggest you begin by filling in the first few
units and keep track of how long each unit is taking you. After you have
done the first few units, you (and your tutor) should be able to come up
with a realistic schedule for the rest of the course.
Planned
completion
date
Unit
or event
Actual
completion
date
Time
required
(hours)
Action
needed
Unit 17
Contact tutor
re lab schedule.
Unit 18
Complete Self Test 1.

See below, Note 1.
Preview
Unit 19
Unit 20
Complete Self Test 2
Unit 21
Complete TMA 1
Unit 22
Midterm
Examination
Unit 23
See below, Note 2.
Unit 24

Complete TMA 2
Unit 25
Unit 26, 27 or 28
Complete
Self Test 5, 6 or 7
Review
Final
Examination
Note 1: Check Applying for and Writing Examinations, in this manual, and note,
on the schedule above, the date by which you must apply for the midterm exam.
Note 2: Check Applying for and Writing Examinations, in this manual, and note,
on the schedule above, the date by which you must apply for the final exam.
15
16
Assessment
The assessment of students in this course is based on examinations,
tutor-marked assignments and laboratory work. Details are given in the
table below. To obtain credit for Chemistry 360, you must
obtain an overall (composite) mark of at least 50%.
achieve at least 45% on each of the two examinations.
obtain an average of at least 60% on the tutor-marked assignments.
achieve an average of at least 55% on the laboratory work.
Percentage
of total mark
Component
Material covered
Midterm Examination
(2 hours)
Units 17-22
20%
Final Examination
(3 hours)
Entire Course
50%
Tutor-marked
Assignments
Following Unit 21
and Unit 25
10%
Laboratory Work
20%
All examinations are supervised and closed-book. However, you will be

supplied with a periodic table and a list of appropriate data (constants,
spectral data, etc.).
Remember: You must be sure to have your own electronic calculator and
molecular models with you when you write an examination.
Note that while the emphasis of the final examination is on the material
covered in Units 23-25 and the optional unit, you are still responsible for the
material covered in Units 17-22. In addition, both midterm and final
examinations assume you still have the skills and knowledge gained in
your previous organic chemistry course.
The hints given below may help you to write examinations successfully.
1. Write only when you and your tutor feel that you are adequately
prepared, and when you have successfully completed the relevant
tutor-marked assignments. Remember that the examination is based on
the objectives outlined in the Study Guide. Many of the questions will be
similar in format to those given in the tutor-marked assignments.
2. For short answer questions, do the ones that you find easiest first. This
procedure has two benefits. First, you can more quickly accumulate
enough marks to pass the examination. Second, you gain confidence to
tackle the harder questions.
17
3. For numerical problems, show your work! Part marks will be given for
correct methods even if your answer is incorrect. The answers to
numerical problems should be given to the correct number of significant
figures, and where appropriate, with the correct units. Marks may be
deducted if answers are given to an incorrect number of significant
figures or in the wrong (or no) units.
Procedures for applying to write examinations may be found in the section
of this Student Manual titled Applying for an Examination, below.
Applying for and Writing Examinations

If you are requesting to write an examination at Athabasca University
(Athabasca), Athabasca University (Edmonton), or Athabasca University
(Calgary), you must request your examination 10 calendar days before your
requested write date.
If you live within Canada or the United States and are requesting an
examination to be written at an established Athabasca University Approved
Invigilation Centre, you must request your examination 20 calendar days
before your requested write date.
If you live outside of Canada and the United States and are requesting an
examination to be written at an established Athabasca University Approved
Invigilation Centre, your request must be received 30 calendar days before
your requested write date.
If you are requesting to write your examination using an invigilator who is
not established as an Athabasca University Approved Invigilator, your
request must be received 60 calendar days before your requested write date.
To request an examination, follow the steps below.
1. Review the Examinations and Grades section of the current Athabasca
University Calendar.
2. Arrange for a time to write your examination with one of Athabasca
Universitys Examination Centres or with an invigilator. For a list of
Examination Centres, see the website
http://www.athabascau.ca/registrar/invignet.php
If you would like to use an invigilator who has not been approved by the
Office of the Registrar, you may propose their approval by filling in the
appropriate details on the online Examination Request Form. Keep in
mind that invigilators may charge a fee, for which you will be
responsible.
3. Complete and submit the online Examination Request Form. If you do
not have access to the Internet, fill out the Examination Request Form
you received from the Office of the Registrar, and submit it by fax
18
(780.675.6174), or in person or by postal mail to Examination Services,

Office of the Registrar, at Athabasca University, Athabasca.
Note: To minimize the time required to process your application, be sure
that you provide all of the information requested on the form, and that
you write legibly.
4. Confirm that your invigilator has received the examination package
before you arrive to write your examination. Take picture identification
and your student number with you when you go to the examination site.
After you have written an examination, please be patient while you wait for
the result. Examinations rarely reach our central offices in less than five
days, and a ten-day lapse from when the examination is written to its arrival
in Athabasca is not unusual. Chemistry examinations are normally marked
within twenty-four hours of receipt, and your tutor is informed of the mark
before your next tutor night. Writing an examination one day and calling the
course professor a day or two later does not expedite the marking process.
For security reasons, examinations cannot be returned to students, nor can
the professor enter into detailed discussions of specific examination
questions. After each of your examinations is corrected, some written
comments will be sent to you. Your tutor will also receive a copy of these
comments, and you should discuss the issues raised with your tutor on the
first suitable occasion.
Supplemental Examinations
Students who are dissatisfied with their grade on any examination, or who
obtain less than the required passing grade, may write a supplemental
examination. Only one supplemental is permitted per examination. The
higher of the two grades received will be recorded as the official grade.
Note that there is a fee for each supplemental examination.
Appeals
Appeals to examination or assignment grades should be discussed first with
your tutor or instructor. For the correct procedure, see Student Code of
Conduct and Right to Appeal in the current Athabasca University Calendar
or available through your myAU portal.
19
Student Conduct and Appeals

Three policies in particular govern the conduct of students of Athabasca
University:
the Non-Academic Misconduct Policy,
the Academic Misconduct Policy and
the Student Academic Appeals Committee Policy, also known as the
Academic Appeals Policy.

You are responsible for reading these policies carefully, as they affect your
studies and your role as an Athabasca University student.
Links to these policies are provided though your myAU portal. Click on the
Student Services tab near the top of your myAU web page. Links to the
policies affecting students are given in the Policies and Standards section
at the bottom right-hand side of the Student Services page. We encourage
you to read all of the policies on this list.
Note: All of the assignments you submit for this course must be original
work completed especially for the course. The use of assignments
completed for other courses, or assignments from other students, both are
considered cheating, and will be penalized as such.
Intellectual Indebtedness
Students enrolled in any Athabasca University course are considered to be
responsible scholars, and are therefore expected to adhere rigorously to the
principles of intellectual honesty.
Plagiarism is a form of intellectual dishonesty in which anothers work is
presented as ones own, and, as will any form of academic misconduct,
plagiarism will be severely penalized. Depending on the circumstances,
penalties may involve rejection of the submitted work; expulsion from the
examination, the course or the program; or legal action.
Students sometimes commit plagiarism inadvertently. To avoid doing so,
make certain that you acknowledge all your sourcesboth primary and
secondaryin a full and consistent manner. All direct quotes (quotations,
however short, from an original work), indirect quotes, paraphrased
passages, ideas, images, and tabular and statistical information that you use
from other sources (including electronic sources) must be documented
using an acceptable citation style. There are three conventional ways of
acknowledging your sources: in-text citations, footnotes or end-notes. We
prefer that you use in-text citations, combined with a full bibliography
presented at the end of the essay. The in-text citation must give the name of
the author, the date of publication, and the page on which the cited material
appears (Doe, 1997, p. 60). The bibliographic entry must provide at least the
authors last name, first name or initial, the date of publication, the title of
the work, the place of publication and the publisher.
20
Transcripts
A student can request an official transcript by completing a paper
Transcript Request form, by writing to the Office of the Registrar, by
appearing at the Office of the Registrar in person, or by using the secure
online request form. For instructions on making an online request, see
http://www.athabascau.ca/registrar/OROShelp.php?page=transcriptRequest
Only the student whose transcript is being issued may make the request,
and a paper request must bear the students signature.
No partial transcripts are issued. The students entire record is shown on
each transcript.
Most institutions and agencies require that official transcripts be sent
directly from Athabasca University. Please allow a minimum of ten working
days for the receipt of a transcript. Consult the current edition of the
Athabasca University Calendar for further information about transcripts.
Transferring Credit
If you wish to transfer credit to another institution, contact the Office of the
Registrar at Athabasca University. Remember, however, that transfer of
credit is determined by the receiving institution. If you plan to transfer credit
for this course to another institution, we suggest you get an agreement, in
writing, from that institution. This agreement is usually called a letter of
permission.
Applying for Extensions

If you are unable to complete this course within the six-month course
contract period, you may apply for and purchase up to three, two-month
extensions. Note that extension request forms must be received by the
Office of the Registrar a minimum of one month before the end of your
course contract. Requests for second and third extensions must be received
by the Office of the Registrar a minimum of one month before the expiry of
the previous extension. Consult the online Athabasca University Calendar for
more information about obtaining extensions.
21
22
Sample Examinations
On the following pages you will find sample examinations that will help
you prepare for your midterm examination and your final examination. We
have included such questions in this manual to give you a better idea of the
length of a normal Athabasca University chemistry examination. Short
answers for the questions are given at the end of the sample examinations
(see the section of this manual titled Sample Examination Answer Keys).
23
24
Sample Midterm Examination

The midterm examination is two (2) hours long. In the actual examination,
you will not be allowed to consult your books or notes; however, you will
be permitted to use a calculator or slide rule. You will also be provided with
a periodic table and a set of 1 H NMR chemical shifts and infrared stretching
frequencies.
Part A: Short Questions (3 marks each)
1. Provide the IUPAC name for each of the compounds below. Indicate
stereochemistry as appropriate.
IUPAC name:
a.
O
b.
SH
c.
25
2. Draw the appropriate structure for each of the compounds below.

a. 1, 2-epoxybutane
b. N,N-dimethylacetamide
c. 5-hydroxy pentanenitrile
3. Rank the acidity of the compounds below (1 = most acidic; 3 = least

acidic).
O
OH
OH
26
OH
O
4. Draw all the resonance forms for the following species:

O
5. Circle the secondary thiol

S
SH
SH
6. Draw the mechanism showing the acid catalyzed hydration of acetone.

O
H3 O+
EGGGGGGGGC
GGGGGGGG
HO
OH
27
7. Identify regents (a)-(c) in the following scheme:

O
O
GGGGGGGGA
(b)
OH
H
D GGGGGGGG
OH
GGGGGGGGA
(a)
(c)
8. Sketch the 1 H NMR spectrum of ethyl acetate:
For each signal, indicate intensity, multiplicity and chemical shift.
ppm
28
9. What properties account for the fact that acetic acid is a stronger acid
than ethanol?
10. Compound A, C2 H4 O, shows an infrared absorption at 1715 cm1 and

an 1 H NMR spectrum as detailed below.
Signal (ppm)
Intensity
Multiplicity
9.8
quartet
2.2
doublet
Propose a structure for Compound A, and justify your answer.
29
Part B: Longer Questions (marks indicated)

14 marks
11. Identify the major product or products for seven (7) of the following
reactions, and show stereochemistry where appropriate.
Note: Only the first seven questions answered will be markedso
only give answers for those items you want marked.
O
a.
1. CH3 MgBr
GGGGGGGGGGGGGGGA , ether
2. H3 O+
HCN
GGGGGGGGA
b.
O
c.
30
NH2 OH
GGGGGGGGGGGGA
OH
d.
PCC
GGGGGGGGGGGA
CH2 Cl2
NH2
e.
SOCl2
GGGGGGGGGGA
H Br
GGGGGGGGA
f.
O
O
g.
OH
O
O
GGGGGGGGGGGGGGGGGGA
OH
N
31
h.
l2
GGGGGGGGGGGGGGGA
H2 O
SH
O
Cl
i.
OH
GGGGGGGGGGGGGGGGGGGA
1. O3
GGGGGGGGGGGGGGGGGGGGA
2. Zn, CH3 CO2 H
j.
k.
2 NH3
GGGGGGGGGGA
32
12 marks
12. Show by means of a series of chemical equations how three (3) of the
following conversions could be achieved.
Note: Only the first three questions answered will be markedso only
give answers for those items you want marked.
OH
a.
O
GGGGGGGGA
O
OH
b.
GGGGGGGGA
33
c.
GGGGGGGGA
OH
O
d.
8 marks
GGGGGGGGA
13. Write the complete stepwise mechanism for the reaction shown below.
Show all intermediate structures and mark electron flows with arrows.
NH2
O
34
OH
H3 O+
FGGGGGGGGB
GGGGGGGG
+ NH4+
O
6 marks
14. Give a brief definition for three (3) of the following terms. Use
examples where appropriate.
a. mercapto group
b. carbinolamine
c. Fischer esterification reaction
d. thioester
e. enolate ion
f. , -unsaturated carbonyl compound
35
7 marks
15. An unknown Compound A shows the molecular ion M+ at m/z 114

(C7 H14 O), with a single major fragment at m/z 71.
The infrared spectrum of Compound A displays a strong absorption
band at 1715 cm1 , and its 1 H NMR spectrum is shown below.
Derive the structure of Compound A. Justify your answer.
[7 marks]
1 H NMR
6H
1H
ppm
END OF EXAMINATION
36
Sample Final Examination

The final examination is three (3) hours long. In the actual examination, you
will not be allowed to consult your books or notes; however, you will be
permitted to use a calculator or slide rule. You will also be provided with a
periodic table and a set of 1 H NMR chemical shifts and infrared stretching
frequencies.
Part A: Short Questions (3 marks each, unless otherwise noted)
1 mark each
1. Provide the IUPAC name for each of the compounds below.

IUPAC name:
a.
N
H
O
b.
CN
O
Cl
c.
SH
d.
Br
e.
f.
Li Cu(CH3 )2
NH2
37
1 mark each
2. Draw the IUPAC the chemical structure for each of the compounds below.
a.
D-glyceraldehyde
b. N,N-dimethyl cyclopentylamine
c. (S) 4-bromo-2-hexanone
d. 2-ethylcyclohexane-1,3-dione
e. 2-butene-1-thiol
f. 3-chloropyridine
38
3. Rank the basicity of the amines below (1 = least basic, 3 = most basic)
NH2
H2 N
CH2 CH3
N
H
4. Write the resonance structures for the anion below.

O
39
5. a. What alkyl halide would you use to prepare 4-phenylbutanoic acid

using the malonic ester synthesis?
b. What alkyl halide would you use to prepare 4-phenyl-2-butanone

using the acetoacetic ester synthesis?
6. a. What is the structure of the carboxylic acid precursor to

3-methylaniline
CH3
NH2
when prepared by the Curtius reaction?
b. Is the structure of this carboxylic acid the same as or different from the
structure of the carboxylic acid needed to prepare 3-methylaniline by
the Hofmann reaction?
40
7. a. Circle the most stable stable cation
+
+
b. Circle the optically active compound
CH2 OH
Cl
H
CH3
Cl
H3 C
CHO
HO
H
Br
Cl
OH
H
OH
CH2 OH
8. Draw the structure of the carbonyl compound whose 1 H NMR spectrum

is summarized in the table below.
Chemical shift
(ppm)
Signal
multiplicity
2.1
singlet
(3 H)
2.4
quartet
(2 H)
1.1
triplet
(3 H)
41
Part B: Longer Questions (marks indicated)

20 marks
9. State the major product or products for ten (10) of the reactions below.
Note: Only the first ten questions answered will be markedso only
a.
HO
O
H
HNO3
GGGGGGGGGGGGGGGGA
OH
CH2 OH
NO2
b.
1. SnCl2 , HCl
GGGGGGGGGGGGGGGGGGGGGA
2. HNO2 , H2 SO4
3. NaI
MgBr
1.
c.
42
CN GGGGGGGGGGGGGGGGGGGGGA
2. H3 O+
O
1. Br2 , PBr3
OH GGGGGGGGGGGGGGGGA
2. H2 O
d.
e.
+
O
1. SOCl2
f.
2.
OH
g.
1. THF
GGGGGGGGGGGGGGGGA
2. H+
1. NaOCH3 , CH3 OH
GGGGGGGGGGGGGGGGGGGGGGGGGA
2. H3 O+
43
h.
O
i.
NH2 NH2
GGGGGGGGGGGGA
KOH
H
.
CrO3
GGGGGGGGGGGGGGGGA
H3 O+
OH
pyridine
1.
Cl
GGGGGGGGGGGGGGGGGGGGGGGA
O
2. CH3 OH, HCl
H
j.
44
O
NaOCH3 , CH3 OH
k.
SH
l.
l2
GGGGGGGGGGGGGGA
H2 O
m.
+ (C6 H5 )3 P C H
CH3
GGGGGGGGGGGGGGA
OH
n.
PCC
OH GGGGGGGGGGGGGGA
CH2 Cl2
45
10 marks
10. In your own words, define five (5) of the terms given below.
Note: Only the first five questions answered will be markedso only
a. heterocyclic amine
b. mutarotation
c. chemical shift
d. parent peak
e. enol
f. anomers
g. Hell Volhard-Zelinskii reaction
h. mixed aldol
i. ,-unsaturated ester
46
10 marks
11. Propose the step-wise mechanism for each of the transformations

below. Use arrows to show electron flow where appropriate.
a.
+
NH2
N HSO4
NH2
N
b.
O
H
GGGGGGGGA
NaOH
GGGGGGGGGGGGGG
AG
D GGGGGGGGGGGGG
ethanol
OH
O
H
47
10 marks
12. Propose and show the synthetic pathway for two of the
transformations below.
Note: Only the first two questions answered will be markedso only
CN
NH2
a.
GGGGGGGGA
b.
GGGGGGGGA
O
c.
48
HO
O
O
GGGGGGGGA
10 marks
13. a. Compound A, C10 H18 O undergoes reaction with dilute H2 SO4 at

25 C to yield two alkenes, C10 H16 , B and C. The major alkene
product B gives only cyclopentanone after ozone treatment
followed by reduction with zinc in acetic acid.
Identify A, B and C.
b. Compound A is a D-aldopentose C5 H10 O5 that can be oxidized to

an optically inactive aldaric acid B on treatment with HNO3 .
On Kiliani-Fischer chain extension, Compound A is converted to
compounds C and D: Compound C can be oxidized to an optically
active aldaric acid E, where as Compound D is oxidized to an
optically inactive aldaric acid F.
What are the structures of A to F?
49
Note: The remainder of this examination is based on the three optional units
in this course. You have studied one of the possible three units. Please
complete only one (1) of the following questions
Unit 26
10 marks
Biomolecules: Amino Acids, Peptides and Protein
15. Threonine, (2S, 3R)-2-amino-3-hydroxybutanoic acid, has two chirality

centres.
a. Draw the Fischer projection of threonine
b. Draw the predominant form of threonine in a pH 4.0 buffer solution.

The isoelectric point of threonine is 5.6.
c. Use the amidomalonate synthesis to prepare the amino acid

phenylalanine beginning with diethyl acetamidomalonate.
50
Unit 27
10 marks
16. a. Draw the major products you would expect from the reaction of
cholesterol and the following reagents
HO
Cholesterol
i.
CrO3
GGGGGGGGGGGGGGA
H+
ii.
O
pyridine
iii.
Br2
GGGGGGGGGGGGGGA
CH2 Cl2
51
b. Draw the molecules below in chair conformations, and indicate

whether the bridgehead methyl is axial or equatorial.
i.
ii.
52
Unit 28
10 marks
17. a. Describe, using chemical structures, two major structural differences

between DNA and RNA.
b. Explain each of the following terms:

i. replication
ii. messenger RNA
iii. coding strand
c. What RNA base sequence is complementary to the DNA base sequence

below?
(5 ) G A T T A C C G T A(3 ) end
END OF EXAMINATION
53
54
Sample Examination Answer Keys
55
56
Sample Midterm Examination

Part A:
1. Provide the IUPAC name for each of the compounds below. Indicate
stereochemistry as appropriate.
IUPAC name:
a.
cyclopentyl 2-methylpropanoate
O
b.
1-methoxycyclohexene
SH
c.
(R)3-heptanethiol
57
2. Draw the appropriate structure for each of the compounds below.

a. 1, 2-epoxybutane
O
b. N,N-dimethylacetamide
O
N
c. 5-hydroxy pentanenitrile
HO
CN
3. Rank the acidity of the compounds below (1 = most acidic; 3 = least

acidic).
O
OH
OH
58
OH
O
4. Draw all the resonance forms for the following species:

O
5. Circle the secondary thiol
SH
SH
6. Draw the mechanism showing the acid catalyzed hydration of acetone.
EGGGGGGC
GGGGGG
H2 O
HO
H3 O+
EGGGGGGGGC
GGGGGGGG
H2 O
OH
+ OH
FGGGB
GGG
OH
FGGGB
GGG
+
H
O+
+ H3 O+
OH
59
7. Identify regents (a)-(c) in the following scheme:

O
LiAlH4
GGGGGGGGGGGGA
ether
OH
OH
PCC
GGGGGGGGGA
CH2 Cl2
NH2 NH2
GGGGGGGGGGGGGGA
KOH
8. Sketch the 1 H NMR spectrum of ethyl acetate:
For each signal, indicate intensity, multiplicity and chemical shift.
O
CH3C
3H
CH
3H
OCH2
2H
8
ppm
60
3
~3.5 ppm
2
1
~2.0 ppm ~1.0 ppm
9. What properties account for the fact that acetic acid is a stronger acid
than ethanol?
O
FGGGGGGB
GGGGGG
OH
GGGGGG
OH FGGGGGGB
Resonance stabilization of carboxylate anion accounts for increased

acidity of acetic acid compared to ethanol.
10. Compound A, C2 H4 O, shows an infrared absorption at 1715 cm1 and

an 1 H NMR spectrum as detailed below.
Signal (ppm)
Intensity
Multiplicity
9.8
quartet
2.2
doublet
Propose a structure for Compound A, and justify your answer.

degrees of unsaturation = 1
1715 cm1
O
H3 C
d 2.2 ppm
H
q 9.8 ppm
61
Part B: Longer Questions

11. Identify the major product or products for seven (7) of the following
reactions, and show stereochemistry where appropriate.
Note: Only the first seven questions answered will be markedso
only give answers for those items you want marked.
O
a.
1. CH3 MgBr
GGGGGGGGGGGGGGGA
either
2. H3 O+
HCN
GGGGGGGGGA
b.
62
OH
O
c.
NC
or
OH
NH2 OH
GGGGGGGGGGGGA
OH
O
OH
d.
PCC
GGGGGGGGGGGA
CH2 Cl2
NH2
e.
CN
SOCl2
GGGGGGGGGGA
OH
H Br
GGGGGGGGA
f.
Br
O
O
g.
OH
O
O
OH O
GGGGGGGGGGGGGGGGGGA
OH
N
63
h.
l2
GGGGGGGGGGGGGGGA
H2 O
SH
O
Cl
i.
OH
1. O3
2. Zn, CH3 CO2 H
j.
k.
O
64
2 NH3
GGGGGGGGGGA
O+
O
O
NH4+
+
NH2
12. Show by means of a series of chemical equations how three (3) of the
following conversions could be achieved.
a.
OH
CrO3
D GGGGGGGGG
pyridine
GGGGGGGGGGGGGA
D GGGGGGGGGGG
Br2 /PBr3
GGGGGGGGGGGGGGA
Br
O
OH
b.
H3 O+
GGGGGGGGGGA
CrO3
D GGGGGGGGGGGGGGG
H3 O+ , acetone
GGGGGGGGA
O
NaOH
GGGGGGGGGGGA
ethanol
HO
65
66
CH3 Cl
D GGGGGGGGGGG
AlCl3
c. Either
or
KMnO4
D GGGGGGGGGGGG
CH3 Cl
D GGGGGGGGGGG
AlCl3
GGGGGGGGGGGA
NBS
GGGGGGGGGGGA
CH2 Cl2
GGGGGGGGGGGA
CO2 H
LiAlH4
GGGGGGGGGGGA
ether
Br
OH
Na OCH3
GGGGGGGGGGGGGGGA
CH3 OH
1. NaOH
GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGA
2. CH3 Br
d.
OH
GGG
GGG
GGG BH
H GGGGG 3
2O
G
2 , O GGGG
H GGGA
PPh3
Br
D GGGGGGGGGGGGGGGGGGGGGG
GGGGGGGGGGGA
13. Write the complete stepwise mechanism for the reaction shown below.
Show all intermediate structures and mark electron flows with arrows.
NH2
O
FGGGGGGB
GGGGGG
HO+
NH2 FGGGGGGB
GGGGGG
OH
NH2
FGGGGGGGGB
GGGGGGGG
+H
+ NH4+
G GBGG
GGG
G GG G
G GG G
G GG G
G GG G
GFGG
OH
H3 O+
GGGGGGB
F GGGGGG
NH3
OH
67
14. Give a brief definition for three (3) of the following terms. Use
examples where appropriate.
a. mercapto group
a thiol
SH
b. carbinolamine
C
OH
NH2
c. Fischer esterification reaction

an acid catalyzed reaction between a carboxylic acid and an alcohol
O
O
R
H+
OH + R OH FGGGGGGB
GGGGGG R
OR + H2 O
d. thioester
O
SR
e. enolate ion
O
f. , -unsaturated carbonyl compound

O
68
15. An unknown Compound A shows the molecular ion M+ at m/z 114

(C7 H14 O), with a single major fragment at m/z 71 in its mass spectrum.
The infrared spectrum of Compound A displays a strong absorption
band at 1715 cm1 , and its 1 H NMR spectrum is shown below.
Derive the structure of Compound A. Justify your answer.
1 H NMR
6H
1H
ppm
degree of unsaturation = 1
1715 cm1
C=O
CH3
NMR
H
CH3
14H 7H = 7H; therefore, the molecule is symmetrical.

O
MS
CH3
major fragment
CH
m/z 28
CH3
m/z 43
m/z 71
Compound A:
O
H3 C
H
H3 C
CH3
C
H
CH3
END OF EXAMINATION
69
70
Sample Final Examination

The final examination is three (3) hours long. In the actual examination, you
will not be allowed to consult your books or notes; however, you will be
permitted to use a calculator or slide rule. You will also be provided with a
periodic table and a set of 1 H NMR chemical shifts and infrared stretching
frequencies.
Part A:
1. Provide the IUPAC name for each of the compounds below.
IUPAC name:
a.
pyrrolidine
N
H
O
b.
3-cyano-2-cyclohexen-1-one
CN
O
Cl
c.
2-chlorocyclopentanone
SH
d.
4-bromobenzenethiol
Br
e.
f.
Li Cu(CH3 )2
NH2
lithium dimethylcuprate
aniline
71
2. Draw the IUPAC the chemical structure for each of the compounds below.
a.
D-glyceraldehyde
OH
CH2 OH
b. N,N-dimethyl cyclopentylamine
N
c. (S) 4-bromo-2-hexanone
H
O
Br
d. 2-ethylcyclohexane-1,3-dione
O
O
e. 2-butene-1-thiol
SH
f. 3-chloropyridine
Cl
72
3. Rank the basicity of the amines below (1 = least basic, 3 = most basic)
NH2
H2 N
CH2 CH3
N
H
4. Write the resonance structures for the anion below.

O
There are three resonance structures.
73
5. a. What alkyl halide would you use to prepare 4-phenylbutanoic acid

using the malonic ester synthesis?
Br
CH2 (CO2 R )2
b. What alkyl halide would you use to prepare 4-phenyl-2-butanone

using the acetoacetic ester synthesis?
O
+
Br
O
OR
6. a. What is the structure of the carboxylic acid precursor to

3-methylaniline
CH3
NH2
when prepared by the Curtius reaction?
CH3
CO2 H
b. Is the structure of this carboxylic acid the same as or different from the
structure of the carboxylic acid needed to prepare 3-methylaniline by
the Hofmann reaction?
It is the same.
74
7. a. Circle the most stable stable cation
+
+
2 , allylic
b. Circle the optically active compound
CH2 OH
Cl
H
CH3
Cl
H3 C
CHO
HO
H
Br
Cl
OH
H
OH
CH2 OH
8. Draw the structure of the carbonyl compound whose 1 H NMR spectrum

is summarized in the table below.
Chemical shift
(ppm)
Signal
multiplicity
2.1
singlet
(3 H)
2.4
quartet
(2 H)
1.1
triplet
(3 H)
75
Part B: Longer Questions

9. State the major product or products for ten (10) of the reactions below.
Note: Only the first ten questions answered will be markedso only
a.
HO
O
H
CO2 H
HO
HNO3
GGGGGGGGGGGGGGGGA
OH
OH
CO2 H
CH2 OH
NO2
b.
1. SnCl2 , HCl
GGGGGGGGGGGGGGGGGGGGGA
2. HNO2 , H2 SO4
3. Nal
HSO4
$ GGGA
"
MgBr
1.
c.
CN GGGGGGGGGGGGGGGGGGGGGA
2. H3 O+
76
d.
O
1. Br2 , PBr3
OH GGGGGGGGGGGGGGGA
2. H2 O
OH
Br
e.
+
O
1. THF
GGGGGGGGGGA
2. H+
1. SOCl2
f.
2.
OH
g.
O
GGGGGGGGGGGA
1. NaOCH3 , CH3 OH
GGGGGGGGGGGGGGGGGGGGGGGGGA
2. H3 O+
OH
77
h.
O
i.
NH2 NH2
GGGGGGGGGGGGA
KOH
H
.
CrO3
GGGGGGGGGGGGGGGGA
H3 O+
1.
pyridine
Cl
O
2. CH3 OH, HCl
H
j.
78
OH
OH
k.
O
OCH3
.
NaOCH3 , CH3 OH
SH
l.
m.
l2
GGGGGGGGGGGGGGA
H2 O
(C6 H5 )3 P C H
CH3
GGGGGGGGGGA
CHCH3
OH
n.
O
PCC
OH GGGGGGGGGGGGA
CH2 Cl2
O
79
10. In your own words, define five (5) of the terms given below.
Note: Only the first five questions answered will be markedso only
a. heterocyclic amine
compounds in which the N atom occurs as part of ring; for
example, pyridine,
N
b. mutarotation
change in optical rotation observed when a pure anomer is
dissolved in water; it is caused by reversible opening and closing of
the hemiacetal, which gives a mixture of anomers
c. chemical shift
the position in a 1 H NMR spectrum where a nucleus absorbs
d. parent peak
the peak in the mass spectrum corresponding to the molecular
ion, M+
e. enol
a vinyl alcohol,
OH
f. anomers
cyclic stereoisomers of sugars that differ only in their configuration
at the hemiacetal (anomeric) carbon
g. Hell Volhard-Zelinskii reaction
formation of an -bromo carboxylic acid
1. Br2
RCH2 CO2 H GGGGGGGGGGA
RC HCO2 H
PBr3
Br
2. H2 O
h. mixed aldol
aldol reaction between one or more aldehydes and one or more
ketones, one of which has no H and thus cannot form an
enolate ion
i. ,-unsaturated ester
OR
80
11. Propose the step-wise mechanism for each of the transformations

below. Use arrows to show electron flow where appropriate.
a.
+
N HSO4
NH2
NH2
N
GGGGGGGGA
GGG
GGG
G
G
GGG
GGG
G
G
GGG
NH2
OH
NaOH
GGGGGGGGGGGGGG
AG
D
GGGGGGGGGGGGG
H
ethanol
H2 SO4
O
H
!
H
EGGGGGGGGC
GGGGGGGG
OH
HSO4
b.
+ H2 O
H
H
H
O
H
+ OH
BG
FGGGGGGGGGG
GGGGGGGGG
O
81
12. Propose and show the synthetic pathway for two of the
transformations below.
Note: Only the first two questions answered will be markedso only
a. Either
CN
NH2
1. NaN3
GGGGGGGGGGGGGGGGA
2. H2 O/
1. NaOH
D GGGGGGGGGGGGGG
2. H3 O+
GGGGGGGGA
O
OH
SOCl2
GGGGGGGGGGGGGG
A
Cl
or
CN
NH2
1. NH3
2. Br2 /NaOH
H2 O
1. NaOH
D GGGGGGGGGGGGGG
2. H3 O+
GGGGGGGGA
OH
82
SOCl2
GGGGGGGGGGGGGG
A
Cl
O
HO
1. HNO3 , H2 SO4
D GGGGGGGGGGGGGGGGGGGGGGG
GGGGGGGGGGGGGGGGA
HSO4
+
O2 N
c.
1. SnCl2 /HCl
2. HNO2 /H2 SO4
O
GGGGGGGGA
Br
product
2.
1. NaOEt/EtOH
D GGGGGGGGGGGGGGGGGGGGGGG
Cu2 O/Cu(NO3 )2 /H2 O

GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGA
b.
O
1. H3 O+
GGGGGGGGGGGA
2. heat
O
product + CO2 + EtOH
OEt
83
13. a. Compound A, C10 H18 O undergoes reaction with dilute H2 SO4 at

25 C to yield two alkenes, C10 H16 , B and C. The major alkene
product B gives only cyclopentanone after ozone treatment
followed by reduction with zinc in acetic acid.
Identify A, B and C.
dil H2 SO4
GGGGGGGGGGGGA
B
C10 H16
degree of
unsaturation = 3
C
C10 H16
O3
D GGGGGGGGG
2n/HoAc
A
C10 H18 O
degree of
unsaturation = 2
B is
OH
A must be
and C should be
84
b. Compound A is a D-aldopentose C5 H10 O5 that can be oxidized to

an optically inactive aldaric acid B on treatment with HNO3 .
On Kiliani-Fischer chain extension, Compound A is converted to
compounds C and D: Compound C can be oxidized to an optically
active aldaric acid E, where as Compound D is oxidized to an
optically inactive aldaric acid F.
What are the structures of A to F?
CHO
CHO
OH
OH
OH
Kiliani
GGGGGGA
Fischer
OH
OH
OH
OH
OH
CH2 OH
CH2 OH
HNO3
D GGGGGGGGGGG
HNO3
D GGGGGGGGGGG
OH
CH2 OH
CO2 H
CO2 H
OH
B
HO
OH
OH
CO2 H
HNO3
D GGGGGGGGGGG
OH
CHO
CO2 H
HO
E
OH
F
OH
OH
OH
OH
OH
OH
CO2 H
CO2 H
optically
active
optically
inactive
Therefore,
CHO
CO2 H
OH
OH
OH
D is
OH
OH
CH2 OH
OH
F is
OH
OH
CO2 H
85
CHO
CO2 H
HO
HO
OH
C is
OH
OH
E is
OH
OH
OH
CH2 OH
CO2 H
CO2 H
CHO
OH
A is
OH
OH
CH2 OH
86
OH
B is
OH
OH
CO2 H
Note: The remainder of this examination is based on the three optional units
in this course. You have studied one of the possible three units. Please
complete only one (1) of the following questions
Biomolecules: Amino Acids, Peptides and Protein
Unit 26
15. Threonine, (2S, 3R)-2-amino-3-hydroxybutanoic acid, has two chirality

centres.
a. Draw the Fischer projection of threonine
CO2 H
H2 N
OH
CH3
b. Draw the predominant form of threonine in a pH 4.0 buffer solution.
The isoelectric point of threonine is 5.6.
H
HO
H2 N
c. Use the amidomalonate synthesis to prepare the amino acid

phenylalanine beginning with diethyl acetamido malonate.
CO2 Et
H
C
HN
CO2 Et
C
CH3
1. NaOEt
GGGGGGGGGGGGA PhCH2
2. PhCH2 Br
CO2 Et
C
CO2 Et
HN
H3 O+
GGGGGGGA
heat
PhCH2
CH
CO2
+ NH
3
O
O
87
Unit 27
16. a. Draw the major products you would expect from the reaction of
cholesterol and the following reagents
HO
cholesterol
CrO3
i. GGGGGGGGGGGGGGA
H+
O
O
O
ii. GGGGGGGGGGGGGGGGGGGA
pyridine
O
O
Br2
iii. GGGGGGGGGGGGGGA
CH2 Cl2
.
HO
Br
Br
88
b. Draw the molecules below in chair conformations, and indicate

whether the bridgehead methyl is axial or equatorial.
i.
axial CH3 group
H
ii.
axial CH3 group
89
Unit 28
17. a. Describe, using chemical structures, two major structural differences

between DNA and RNA.
DNA
deoxyribose
RNA
O
O
ribose
unique base
thymine
P OCH2
O
O
base
NH
N
HO
unique base
uracil
P OCH2
O
O
O
base
NH
O
OH OH
sugar
sugar
b. Explain each of the following terms:

i. replication
process by which double-stranded DNA uncoils and is replicated to
produce two new copies
ii. messenger RNA
During transcription, a short segment of the DNA double helix
rewinds and complementary RNA line up to produce mRNA, a
form of RNA that carries genetic messages to ribosomes, the cell
part that manufactures proteins.
iii. coding strand
the strand of double-helical DNA that contains the gene
c. What RNA base sequence is complementary to the DNA base sequence

below?
(5 ) G A T T A C C G T A(3 ) end
RNA (3 ) C U A A U G G C A U(5 ) end
END OF EXAMINATION
90

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Sample Midterm Examination

2. Draw the appropriate structure for each of the compounds below.

3. Rank the acidity of the compounds below (1 = most acidic; 3 = least

Chemistry 360 / Student Manual

4. Draw all the resonance forms for the following species:

5. Circle the secondary thiol

6. Draw the mechanism showing the acid catalyzed hydration of acetone.

7. Identify regents (a)-(c) in the following scheme:

8. Sketch the 1 H NMR spectrum of ethyl acetate:

For each signal, indicate intensity, multiplicity and chemical shift.

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10. Compound A, C2 H4 O, shows an infrared absorption at 1715 cm1 and

Propose a structure for Compound A, and justify your answer.

Part B: Longer Questions (marks indicated)

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