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Chemistry 360
Organic Chemistry II
Student Manual
Note: The Student Manual was prepared primarily for
individualized-studystudents. Students who are taking this course
with seminar support orthrough a co-operating institution should be
aware that some of theinformation will not apply in their
situation. In case of doubt, please askyour tutor or seminar leader
about any problems that might arise. Furtherclarification can be
obtained from the course professor.
Athabasca University
-
Course Team
Course Professor: Lawton ShawCourse Authors: Arthur Last and
Dietmar KennepohlRevisions:Dietmar Kennpohl (1996-2004); Lois
Browne (2010)Reviewer, 2004:David LawEditor: Gilda SandersVisual
Presentation:Athabasca University Digital Media Technology
UnitCover Design: Jingfen Zhang
Note: This course is a revision of a part of Chemistry 345:
Organic Chemistryby Arthur Last, copyright c 1991 by Athabasca
University.
Every effort has been taken to ensure that these materials
comply with therequirements of copyright clearances and appropriate
credits. AthabascaUniversity will attempt to incorporate in future
printings any correctionswhich are communicated to it.
The inclusion of any material in this publication is strictly in
accord with theconsents obtained and Athabasca University does not
authorize or licenseany further reproduction or use without the
consent of the copyright holder.
c Athabasca University 1998, 2003, 2004, 2010All rights
reservedPrinted in Canada
CMID 554275Revision 6
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Contents
The Course . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . 1
The MyAU Portal . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . 1
Your Student ID Number . . . . . . . . . . . . . . . . . . . . .
. . . . . 2
Freedom of Information and Protection of Privacy . . . . . . . .
. . . 2
The Athabasca University Calendar . . . . . . . . . . . . . . .
. . . . 2
Course Materials . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . 3
Other Items . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . 4
Forms . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . 4
Course Design . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . 4
Laboratories . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . 6
Your Tutor . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . 7
The Course Professor . . . . . . . . . . . . . . . . . . . . . .
. . . . . . 8
Services to Students . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . 9
Library Services . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . 10
Study Strategies . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . 12
How to Use the Study Guide . . . . . . . . . . . . . . . . . . .
. . . . 12
Course Outline and Study Schedule . . . . . . . . . . . . . . .
. . . . 14
Assessment . . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . 17
Applying for and Writing Examinations . . . . . . . . . . . . .
. . . . 18
Student Conduct and Appeals . . . . . . . . . . . . . . . . . .
. . . . . 20
Intellectual Indebtedness . . . . . . . . . . . . . . . . . . .
. . . . . . . 20
Transcripts . . . . . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . . 21
Transferring Credit . . . . . . . . . . . . . . . . . . . . . .
. . . . . . . 21
Applying for Extensions . . . . . . . . . . . . . . . . . . . .
. . . . . . 21
Sample Examinations . . . . . . . . . . . . . . . . . . . . . .
. . . . . . 23
Sample Examination Answer Keys . . . . . . . . . . . . . . . . .
. . . 55
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The Course
Welcome to Chemistry 360: Organic Chemistry II, a three-credit,
senior-level,laboratory science course. We assume that all students
registering in thiscourse will have completed Athabasca Universitys
Chemistry 350: OrganicChemistry I, or an equivalent
university-level course in organic chemistry. Ifyou have not done
so, you should contact the course professor immediately.
Organic Chemistry II deals with the chemistry of carbon
compounds througha study of the characteristic reactions of the
common functional groups.Particular emphasis is placed on the study
of reaction mechanisms, in anattempt to show similarities between
apparently unrelated reactions. Theimportance of stereochemistry is
stressed throughout the course. Thecompulsory laboratory component
of Chemistry 360 introduces the studentto the basic techniques
employed in modern organic chemistry laboratories.Experiments have
been selected to illustrate many of the principlesencountered in
the theoretical part of the course. The course outlineprovided in
this manual gives a more detailed description of the
coursecontents.
This Student Manual provides you with some essential information
aboutthe design of the course, the course materials, and the
procedures youshould follow to obtain the maximum benefit from your
studies. Please readit carefully and keep it in a safe place.
Note: These course materials have been designed for students who
aretaking the individualized-study version of this course. Students
who are ina grouped-study environment should follow the course
outline, studyschedule and learning activities provided by their
instructor.
The MyAU Portal
MyAU is a personalized portal to Athabasca University where you
canquickly access information that is relevant to you. Through
myAU, you canview personal information, such as library accounts
and assignment marksand course grades, and take care of
administrative matters, such as bookingexaminations, submitting
assignments, applying for extensions, registeringfor courses and so
on. Athabasca University will also communicate directlywith you
through myAU. Check the Message Centre on your myAU homepage 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 arehaving browser difficulties or you need help, refer to myAU
Help at
http://www.athabascau.ca/uportal/help/index.php
Organic Chemistry II 1
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Your Student ID Number
In contacts with your tutor, on assignments, or in any
correspondence orother contact with the University, you are asked
to provide your student IDnumber. Record this number in the space
below. Having your student IDnumber will help University personnel
to process requests, grades andadministrative matters more
quickly.
Student ID number:
Note: It is important that we receive notification of any change
of address ortelephone number. Please inform the Office of the
Registrar whenever sucha change occurs. You can do so through your
myAU portal, or you can use astudent change of information form
(see the section of this manual titledForms). In addition, you
should send change-of-address cards to yourtutor and to the course
professor, so that your student files can be keptup-to-date.
Freedom of Information and Protection of Privacy
The personal information and records collected and maintained by
theUniversity as a result of a students registration in this
course, such ascompleted assignments and examinations, electronic
communications andcorrespondence, are subject to University
policies and the privacy andaccess provisions of the Alberta
Freedom of Information and Protection ofPrivacy Act.
The Athabasca University Calendar
Because Athabasca Universitys policies, practices, and
procedures changeover time, some of the information in this Student
Manualmay lose itscurrency between course revisions. Students are
therefore advised to referto the current Athabasca University
Calendar on important issues concerningUniversity policies,
procedures and practices. In the event of anydiscrepancy between
the printed version of the Calendar and the officialweb-based
Calendar, the web-based version will be binding.
2 Chemistry 360 / Student Manual
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Course Materials
The package you received should include each of the items listed
below. Ifanything is missing from your package, please contact the
Course Materialsdivision of Athabasca University as soon as
possible. If you live in Canadaor the United States, you can use
email to contact Course Materials:
[email protected]
You can also call 1-800-788-9041, choose option 3 from the menu,
and enterextension 6366 when prompted.
Students who live outside of Canada or the United States can
contactCourse Materials by email.
You can also write in care of Course Materials, Tim Byrne
Centre, 400 Hwy 2South, Athabasca, AB T9S 1A4.
Textbooks
McMurry, John. Organic Chemistry, 7th ed. Pacific Grove, CA:
Brooks/ColePublishing Co., 2008.
McMurry, Susan. Study Guide and Student Solutions Manual for
McMurrysOrganic Chemistry, 7th ed. Pacific Grove, CA: Brooks/Cole
PublishingCo., 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:
AthabascaUniversity, 2010.
The Study Guide, as its name implies, is designed to guide your
study ofthe course textbook.
Chemistry 360: Organic Chemistry II. Assignment Manual.
Athabasca, AB:Athabasca University, 2010.
The Assignment Manual contains the self tests and answers to the
selftests, as well as the two tutor-marked assignments.
Chemistry 360: Organic Chemistry II. Laboratory Manual.
Athabasca, AB:Athabasca University, 2010.
Organic Chemistry II 3
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Other Items
The items listed below are not supplied; you should purchase
them beforeyou 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
anexamination 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, aruler, etc.
Forms
The forms you need to submit assignments, request examinations
or informthe University of a change in your status as a student are
available throughyour myAU home page, or for download from the
Office of the RegistrarsOnline 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 formsonline, please contact the Athabasca University
Information Centre, tollfree, at 1.800.788.9041 to request that
printed copies be sent to you. ForChemistry 360, you will need at
least two tutor-marked exercise forms andtwo examination request
forms.
Course Design
The course materials are designed for self-instruction and
individualized-study. What you should learn and how you should
learn it are described inthe Study Guide. This book contains 16
units, each of which corresponds toone of the chapters in Organic
Chemistry, 7th ed., by John McMurry. Eachunit in the Study Guide
contains a preview, a list of learning objectives, aseries of
subsections corresponding to chapter subsections, and some hintson
how to work through the unit. Let us look at exactly what you can
expectto find under each of these headings.
4 Chemistry 360 / Student Manual
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Unit Preview
The Unit Preview is a brief discussion that outlines the overall
approachtaken 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 tobe able to fulfill when you have finished studying the
unit.
Sections
The sections form the bulk of each unit. Each section in the
Study Guidenormally contains the following features:
1. a list of objectives which are more detailed than those
provided underthe heading Unit Objectives, and which may be one of
the mostvaluable features of the Study Guide, because they tell you
explicitly whatyou need to understand and to be able to do for each
unit of the course.Questions on the examinations and tutor-marked
assignments are basedonly on the unit objectives. However, you
should be aware that manyquestions will require you to demonstrate
mastery of a number of relatedobjectives, and that you should not
place too narrow an interpretation oneach objective.
2. a list of key terms introduced in the section. Unless we have
indicatedotherwise, definitions of these key terms are provided in
AppendixCGlossary, beginning on page A10 of Organic Chemistry, 7th
ed.
3. study notes, which may include hints on how to study the
materialeffectively, additional information, and details of any
errors that occur inthe textbook.
4. a list of suggested exercises. These exercises are designed
to improveyour understanding of the material you have just studied
and to developyour problem-solving skills. Refer to your notes and
to the textbookwhen you attempt the exercises. The answers to all
the exercises areprovided in the Solutions Manual or in Appendix
DAnswers to In-textProblems, beginning on page A30 of the textbook.
Do not spend a largeamount of time on any one exercise. If you are
unable to make anyprogress after a few minutes of concentrated
work, use the answersto help.
For further information, see the section of this manual titled
How to UseYour Study Guide.
Self tests are given at the end of Units 18, 20, 22 and 24, and
after each of theoptional units. These tests are designed to allow
you to measure yourprogress in the coursethey are not a
comprehensive overview of thematerial, nor are they at the same
level of difficulty that you will encounterin the midterm and final
examinations. [Sample examinations are given in
Organic Chemistry II 5
Sukhvir Aujla
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this manual.] If you have difficulty with any self test, you
should go backand review the material before going on.
The textbook by McMurry contains most of the information you
will needto pass this course. It is a standard textbook used in
many universities andcolleges throughout North America. It was
chosen because it offers clearexplanations and interesting
discussions of the material we wished thiscourse to cover. In
addition, we felt that this textbook has an advantage inthat it
includes some discussion of a number of advances made in
organicchemistry during the last decade. The chapters are
relatively short, and thetextbook contains problems, exercises and
some review chapters.
Each chapter of the textbook concludes with a useful summary,
and whereappropriate, a list of the reactions introduced in the
chapter. These reviewsare excellent for quick reference and will
help you to prepare forexaminations.
You should use a set of molecular models to assist you in
understanding thestereochemical aspects of the course. If you
cannot obtain a set of molecularmodels elsewhere, you may order one
from the Athabasca UniversityLibrary (see the section of this
manual titled Library Services). You mayuse molecular models during
examinations.
Laboratories
You must complete about 32 hours of laboratory work to obtain
credit inthis course. Labs are typically held for week-long
sessions during thesummer in Athabasca, or for full-day sessions on
weekends in Edmonton atselected times during the rest of the year.
The Lab Coordinator will be ableto provide up-to-date information,
or you may go to our Lab Informationwebsite at:
http://science.pc.athabascau.ca/labinfo.nsf
You must contact the Lab Coordinator to book into a scheduled
laboratorysession. Students in Canada and the United States can
reach the LabCoordinator by calling 1-800-788-9041 (the extension
is 6276). All studentscan use electronic mail to contact the Lab
Coordinator at
[email protected]
Information about the laboratory program and the experiments to
becarried out is included in the Laboratory Manual. Note that your
lab workaccounts for 20 per cent of your overall course mark. You
must satisfactorilycomplete and write up a specified minimum number
of experiments toobtain credit for this course.
6 Chemistry 360 / Student Manual
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Your Tutor
Athabasca University provides each student in each course with a
tutorwhose responsibility is to help the student complete the
course successfully.A letter containing your tutors name, address,
telephone number andtutoring hours was mailed to you shortly before
your official start date. Ifyou have not yet received your tutor
letter, please contact LearningServicesTutorial at Athabasca
University as soon as possible. Students inCanada or the United
States can call 1-800-788-9041 (extension 6196); allstudents can
send electronic mail to
[email protected]
Note: If you have chosen to receive communications from
AthabascaUniversity in electronic form, be sure to check your myAU
portal for yourtutor letter.
Your tutor has excellent academic qualifications, and is
committed tohelping students learning at a distance. He or she is
available to answeryour questions about course content or how to
approach a problem or anassignment, and can direct you to the right
person or department to helpyou with other problems that may be
hindering your progress in yourcourse or program. In addition, your
tutor will be responsible for markingyour assignments. In general,
you should call your tutor first with anyqueries about Athabasca
University.
The tutor letter will help you become acquainted with your tutor
and willprovide information about your tutors schedule. If you have
not yetreceived 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 thetutor letter. If you live
outside of Canada or the United States, please refer tothe tutor
letter and the current Athabasca University Calendar for
informationabout calling your tutor.
We suggest that you contact your tutor as soon as you receive
the coursematerials, and then get into the habit of communicating
regularly, when youcomplete a unit or when you run into any special
problem. We have foundthat students who maintain regular contact
with their tutors are most likelyto be successful in completing
their courses, so do keep in touch. You mayfind it useful to
schedule a regular study period when your tutor isavailable so that
you can contact him or her when questions arise. If you areunable
to take advantage of the regular tutoring hours, contact your tutor
orthe course professor to determine whether alternative
arrangements can bemade.
If you use postal mail to send an assignment to your tutor, be
sure to attacha tutor-marked exercise form, and to keep a copy, at
least a rough draft, incase the original goes astray in the mail.
If you take this course through theMoodle course management system,
you may be instructed to use theAssignment Drop Box to submit your
assignments. If you wish to submityour assignments electronically
outside of the Moodle system, contact your
Organic Chemistry II 7
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tutor to discuss appropriate formats. An electronic version of
thetutor-marked exercise form is available online through your myAU
portal.
In any case, allow several working days, in addition to mailing
time eachway if applicable, before you expect to receive the graded
assignment. Yourtutor will be pleased to provide additional
feedback. Be sure to mention anyquestions you have about the
assignment or the grade.
Keep your tutors letter of introduction with your course
materials, and usethe 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 ortelephone number. Please inform the Office of
the Registrar whenever sucha change occurs.
The Course Professor
The course professor is the member of Athabasca Universitys
academicstaff who is in charge of a given course. The professor
works directly withtutors on both academic and administrative
matters. If you have difficultiesyou cannot resolve with your
tutor, you may wish to speak with theprofessor directly. You should
also address any questions about creditrecords or centrally marked
examinations to the professor. The professorcan also provide
general information about program planning andcurriculum
development. The course professor welcomes studentscomments on the
course.
8 Chemistry 360 / Student Manual
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Services to Students
Athabasca University offers a wide range of services to its
students. TheAthabasca University Information Centre
(1.800.788.9041) can help you findthe answer to most administrative
questions. The Centre is staffed onregular business days from 7:00
a.m. to 5:30 p.m., Mountain Time.
Advisors are available to assist students in planning their
programs andselecting appropriate courses. Counselors assist
students in improving theirstudy skills and clarifying their
educational goals. You may reach anadvisor or counselor in several
ways: by dialling 1.800.788.9041 and askingto speak with an advisor
or counselor; by visiting Athabasca UniversitysCentral Office in
Athabasca, or the Athabasca University sites in Edmontonor Calgary;
or by directing your query to
http://www.askau.ca
Students who are looking for information about student awards
and adviceabout obtaining financial assistance are asked to contact
the Office of theRegistrar. You may do so by dialling
1.800.788.9041 and asking for the Officeof the Registrar, or by
inquiring through
http://www.askau.ca
Note: Students may write examinations at the Athabasca
University sites inAthabasca, 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 variousadministrative matters, such as course
registration and arrangements forextensions.
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 interestedin identifying culturally appropriate services
designed for Aboriginalstudents or counseling that is sensitive to
the challenges Aboriginalstudents face, please contact the Centre
for World Indigenous Knowledgeand Research, by telephone at
1.800.788.9041, extension 2064, or byelectronic mail at
[email protected]
Organic Chemistry II 9
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Library Services
The Athabasca University Library collection contains more than
140,000books, many periodical titles and a range of audio-visual
resources. TheLibrary subscribes to over 100 online databases,
providing full text access toselected articles from more than
20,000 journals.
Athabasca University Librarys collection primarily supports
AthabascaUniversity courses and programs. Materials found in the
print andelectronic collections are available for use by our
students, faculty and stafffor reference and research purposes.
Requests for library materials orservices can be made, by email,
phone, fax or mail, 24 hours a day (contactinformation is provided
below). Responses to most requests are handledwithin 24 hours, or
by the next business day. Borrowed materials arenormally mailed to
the students home address, along with a return-mail 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
andbook chapters.
Digital Resources
Access to online journal databases, the Digital Reference Centre
(DRC), andthe Digital Reading Room (DRR) is available from
Athabasca UniversityLibrarys main web page
http://library.athabascau.ca
Tips on searching the journal databases and help with
researching, writingand 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 beyondthe contents of the course materials package. Some
Athabasca Universitycourse Study Guides list Supplementary
Materials, including books,
10 Chemistry 360 / Student Manual
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journal articles or audio-visual materials, which students may
find usefulwhen completing assignments and course projects. The
supplementarymaterials referenced in your course materials package
are usually availablefrom the Athabasca University Library or your
local library. Contact theAthabasca University Library to request
materials.
How the Library Gateway Works
The Library website contains the Librarys online catalogue
(AUCAT), and itis also the gateway to other online information. The
website provides linksto journal databases and other subscribed
online resources, as well as toselected, publicly accessible
Internet sites. Subscribed resources areavailable to Athabasca
University students, faculty and staff. You will berequired to
enter your first and last names as your username and yourstudent ID
number as your password.
The Library website also provides access to selected library
catalogues fromCanadian public and academic libraries.
Interlibrary Loans
An interlibrary loan (ILL) involves one library borrowing
materials fromanother on behalf of a library user. Athabasca
University Library willrequest photocopies of journal articles and
book chapters throughInterlibrary Loans, if you provide the Library
staff with a completebibliographic citation (author, title of
article, name of journal, volume andissue number, year of
publication, and page numbers) for the requesteditem. You are not
required to return these items to us. Allow sufficient timefor the
material to be ordered and received. More information on
theInterlibrary Loan process is available on the Library website
at
http://aupac.lib.athabascau.ca/screens/ill.html
Contacts
Athabasca University Library1 University DriveAthabasca, AB
Canada T9S 3A3
Library website: http://library.athabascau.caE-mail:
[email protected]
Phone: 1.800.788.9041 (ext. 6254) Canada/USFax: 780.675.6477
Organic Chemistry II 11
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Study Strategies
Chemistry 360 is a three-credit course and must be completed
within the sixmonths of your contract period. This may seem like a
long time, butprocrastination can rapidly put you in a difficult
position. We suggest youstart right away and that you establish a
study schedule. Your tutor canhelp you.
How fast you proceed through the first few units will depend on
yourbackground in organic chemistry from Chemistry 350. If your
background isweak, you may have to put in extra time, and this may
affect your chancesof completing the course within the normal
six-month contract period. Ifyou find that you really have trouble
with Units 17 and 18, you shoulddiscuss the situation with your
tutor and consider withdrawing from thecourse or taking some action
to improve your understanding offundamental organic chemistry.
At a traditional university, this course would normally be
spread over onesemester and take about 12-13 weeks to complete. If
you wish to attain thisrate, follow the 13-week study schedule
shown in the Course Outline andStudy Schedules section of this
Student Manual. If you wish to proceed atsomewhat slower rate,
refer to the 18- and 24-week schedules when youplan your own
personal study schedule. Remember that regular studyhabits can be a
major contributing factor to ultimate success in this course.Should
unforeseen circumstances put you in a position where you find
thatyou cannot complete the course within six months, check the
AthabascaUniversity Calendar for current regulations about
extensions.
Although the amount of time that a student will need to spend on
thecourse will depend on a variety of factors, students intending
to completethe course in 13 weeks should be prepared to spend at
least nine (9) hoursper week on the course. You may need additional
time when you havelaboratory 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 noteof any questions you have on
content, study procedures, etc. Then, beforeyou 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
outlinedbelow.
1. Read the preview and the list of unit objectives at the
beginning of theunit. At this stage, some students find it
beneficial to obtain an overallpicture of the unit by quickly
reading through the whole chapter in thetextbook.
12 Chemistry 360 / Student Manual
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2. Study each lesson in the unit by
a. reading the objectives and study notes (if any). These notes
maycontain study hints or additional information, and will also
identifyany errors that occur in the relevant section of the
textbook.
b. reading the required pages in the textbook and using the
objectivesand key terms to guide you in making your own notes.
c. completing the assigned exercises and checking your answers
in theStudy Guide and the textbook. Note that your problem-solving
abilitywill 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 cando what they require.
b. making sure that you can define and use the key terms.
c. reading the summary and the summary of reactions
(whereappropriate) given at the end of the chapter in the
textbook.
d. completing a selection of the recommended exercises listed in
theStudy Guide.
4. Do the tutor-marked assignment (if there is one) and send it
to yourtutor, 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 creditfor work that is actually received, we
strongly advise that you keep a roughcopy of all of the work that
you submit to your tutor by mail. Also, pleasemake certain that you
attach a Tutor-marked Exercise form to any workyou mail in for
grading. Student using the Moodle Assignment Drop Boxshould follow
the instructions given on the Moodle course website.
Organic Chemistry II 13
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Course Outline and Study Schedules
The table below gives a brief course outline and suggests the
amount oftime students should spend on each unit for 13-, 18- and
24-week schedules.
Note: Students who are receiving financial assistance may face
special timeconstraints. Please check your course registration for
any restrictions on thelength of registration, and be prepared to
adjust your schedule.
Unit number and title13-weekschedule
18-weekschedule
24-weekschedule
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 CarbonylCompounds
Week 2 Week 2 Week 5
19 Aldehydes and Ketones:Nucleophilic AdditionReactions
Week 3 Weeks 3-4 Weeks 6-7
20 Carboxylic Acids andNitriles
Week 4 Week 5 Week 8
21 Carboxylic AcidDerivatives andNucleophilic AcylSubstitution
Reactions
Week 5 Weeks 6-7 Weeks 9-10
22 CarbonylAlpha-SubstitutionReactions
Week 6 Week 8 Week 11
Review for MidtermExamination
Week 7 Week 9 Week 12
23 Carbonyl CondensationReactions
Week 8 Weeks 10-11 Weeks 13-15
24 Amines and Heterocycles Week 10 Weeks 12-13 Weeks 16-18
25 Biomolecules:Carbohydrates
Week 11 Weeks 14-15 Weeks 19-21
26 Biomolecules: AminoAcids, Peptides, andProteins
Week 12 Weeks 16-17 Weeks 22-23
27 Biomolecules: Lipids Week 12 Weeks 16-17 Weeks 22-23
28 Biomolecules: Nucleic Acids Week 12 Weeks 16-17 Weeks
22-23
Review for FinalExamination
Week 13 Week 18 Week 24
14 Chemistry 360 / Student Manual
-
The table below allows you to plan (with the help of your tutor)
apersonalized study schedule. We suggest you begin by filling in
the first fewunits and keep track of how long each unit is taking
you. After you havedone the first few units, you (and your tutor)
should be able to come upwith a realistic schedule for the rest of
the course.
Planned Actual TimeUnit completion completion required Actionor
event date date (hours) needed
Unit 17 Contact tutorre 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 Complete Self Test 3
MidtermExamination
Unit 23 See below, Note 2.
Unit 24 Complete Self Test 4
Complete TMA 2
Unit 25
Unit 26, 27 or 28 CompleteSelf Test 5, 6 or 7
Review
FinalExamination
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.
Organic Chemistry II 15
-
16 Chemistry 360 / Student Manual
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Assessment
The assessment of students in this course is based on
examinations,tutor-marked assignments and laboratory work. Details
are given in thetable 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.
Component Material coveredPercentageof total mark
Midterm Examination(2 hours)
Units 17-22 20%
Final Examination(3 hours)
Entire Course 50%
Tutor-markedAssignments
Following Unit 21and Unit 25
10%
Laboratory Work 20%
All examinations are supervised and closed-book. However, you
will besupplied 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 andmolecular models with you when you write an
examination.
Note that while the emphasis of the final examination is on the
materialcovered in Units 23-25 and the optional unit, you are still
responsible for thematerial covered in Units 17-22. In addition,
both midterm and finalexaminations assume you still have the skills
and knowledge gained inyour 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
adequatelyprepared, and when you have successfully completed the
relevanttutor-marked assignments. Remember that the examination is
based onthe objectives outlined in the Study Guide. Many of the
questions will besimilar in format to those given in the
tutor-marked assignments.
2. For short answer questions, do the ones that you find easiest
first. Thisprocedure has two benefits. First, you can more quickly
accumulateenough marks to pass the examination. Second, you gain
confidence totackle the harder questions.
Organic Chemistry II 17
Sukhvir Aujla
Sukhvir Aujla
-
3. For numerical problems, show your work! Part marks will be
given forcorrect methods even if your answer is incorrect. The
answers tonumerical problems should be given to the correct number
of significantfigures, and where appropriate, with the correct
units. Marks may bededucted if answers are given to an incorrect
number of significantfigures or in the wrong (or no) units.
Procedures for applying to write examinations may be found in
the sectionof 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 yourrequested write date.
If you live within Canada or the United States and are
requesting anexamination to be written at an established Athabasca
University ApprovedInvigilation Centre, you must request your
examination 20 calendar daysbefore your requested write date.
If you live outside of Canada and the United States and are
requesting anexamination to be written at an established Athabasca
University ApprovedInvigilation Centre, your request must be
received 30 calendar days beforeyour requested write date.
If you are requesting to write your examination using an
invigilator who isnot established as an Athabasca University
Approved Invigilator, yourrequest 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
AthabascaUniversity Calendar.
2. Arrange for a time to write your examination with one of
AthabascaUniversitys Examination Centres or with an invigilator.
For a list ofExamination Centres, see the
websitehttp://www.athabascau.ca/registrar/invignet.php
If you would like to use an invigilator who has not been
approved by theOffice of the Registrar, you may propose their
approval by filling in theappropriate details on the online
Examination Request Form. Keep inmind that invigilators may charge
a fee, for which you will beresponsible.
3. Complete and submit the online Examination Request Form. If
you donot have access to the Internet, fill out the Examination
Request Formyou received from the Office of the Registrar, and
submit it by fax
18 Chemistry 360 / Student Manual
Sukhvir Aujla
-
(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 surethat you provide all of the information requested on the
form, and thatyou write legibly.
4. Confirm that your invigilator has received the examination
packagebefore you arrive to write your examination. Take picture
identificationand your student number with you when you go to the
examination site.
After you have written an examination, please be patient while
you wait forthe result. Examinations rarely reach our central
offices in less than fivedays, and a ten-day lapse fromwhen the
examination is written to its arrivalin Athabasca is not unusual.
Chemistry examinations are normally markedwithin twenty-four hours
of receipt, and your tutor is informed of the markbefore your next
tutor night. Writing an examination one day and calling thecourse
professor a day or two later does not expedite the marking
process.
For security reasons, examinations cannot be returned to
students, nor canthe professor enter into detailed discussions of
specific examinationquestions. After each of your examinations is
corrected, some writtencomments will be sent to you. Your tutor
will also receive a copy of thesecomments, and you should discuss
the issues raised with your tutor on thefirst suitable
occasion.
Supplemental Examinations
Students who are dissatisfied with their grade on any
examination, or whoobtain less than the required passing grade, may
write a supplementalexamination. Only one supplemental is permitted
per examination. Thehigher 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 withyour tutor or instructor. For the correct procedure, see
Student Code ofConduct and Right to Appeal in the current Athabasca
University Calendaror available through your myAU portal.
Organic Chemistry II 19
-
Student Conduct and Appeals
Three policies in particular govern the conduct of students of
AthabascaUniversity:
the Non-Academic Misconduct Policy,
the Academic Misconduct Policy and
the Student Academic Appeals Committee Policy, also known as
theAcademic Appeals Policy.
You are responsible for reading these policies carefully, as
they affect yourstudies and your role as an Athabasca University
student.
Links to these policies are provided though your myAU portal.
Click on theStudent Services tab near the top of your myAU web
page. Links to thepolicies affecting students are given in the
Policies and Standards sectionat the bottom right-hand side of the
Student Services page. We encourageyou to read all of the policies
on this list.
Note: All of the assignments you submit for this course must be
originalwork completed especially for the course. The use of
assignmentscompleted for other courses, or assignments from other
students, both areconsidered cheating, and will be penalized as
such.
Intellectual Indebtedness
Students enrolled in any Athabasca University course are
considered to beresponsible scholars, and are therefore expected to
adhere rigorously to theprinciples of intellectual honesty.
Plagiarism is a form of intellectual dishonesty in which
anothers work ispresented 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 theexamination, 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 andsecondaryin a full and consistent manner. All direct
quotes (quotations,however short, from an original work), indirect
quotes, paraphrasedpassages, ideas, images, and tabular and
statistical information that you usefrom other sources (including
electronic sources) must be documentedusing an acceptable citation
style. There are three conventional ways ofacknowledging your
sources: in-text citations, footnotes or end-notes. Weprefer that
you use in-text citations, combined with a full
bibliographypresented at the end of the essay. The in-text citation
must give the name ofthe author, the date of publication, and the
page on which the cited materialappears (Doe, 1997, p. 60). The
bibliographic entry must provide at least theauthors last name,
first name or initial, the date of publication, the title ofthe
work, the place of publication and the publisher.
20 Chemistry 360 / Student Manual
-
Transcripts
A student can request an official transcript by completing a
paperTranscript Request form, by writing to the Office of the
Registrar, byappearing at the Office of the Registrar in person, or
by using the secureonline 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 oneach transcript.
Most institutions and agencies require that official transcripts
be sentdirectly from Athabasca University. Please allow a minimum
of ten workingdays for the receipt of a transcript. Consult the
current edition of theAthabasca University Calendar for further
information about transcripts.
Transferring Credit
If you wish to transfer credit to another institution, contact
the Office of theRegistrar at Athabasca University. Remember,
however, that transfer ofcredit is determined by the receiving
institution. If you plan to transfer creditfor this course to
another institution, we suggest you get an agreement, inwriting,
from that institution. This agreement is usually called a letter
ofpermission.
Applying for Extensions
If you are unable to complete this course within the six-month
coursecontract period, you may apply for and purchase up to three,
two-monthextensions. Note that extension request forms must be
received by theOffice of the Registrar a minimum of one month
before the end of yourcourse contract. Requests for second and
third extensions must be receivedby the Office of the Registrar a
minimum of one month before the expiry ofthe previous extension.
Consult the online Athabasca University Calendar formore
information about obtaining extensions.
Organic Chemistry II 21
-
22 Chemistry 360 / Student Manual
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Sample Examinations
On the following pages you will find sample examinations that
will helpyou prepare for your midterm examination and your final
examination. Wehave included such questions in this manual to give
you a better idea of thelength of a normal Athabasca University
chemistry examination. Shortanswers for the questions are given at
the end of the sample examinations(see the section of this manual
titled Sample Examination Answer Keys).
Organic Chemistry II 23
-
24 Chemistry 360 / Student Manual
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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 willbe permitted to use a calculator or slide rule.
You will also be provided witha periodic table and a set of 1H NMR
chemical shifts and infrared stretchingfrequencies.
Part A: Short Questions (3 marks each)
1. Provide the IUPAC name for each of the compounds below.
Indicatestereochemistry as appropriate.
IUPAC name:
a. O
O
b.
O
SHH
.c.
Organic Chemistry II 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 =
leastacidic).
O
OHO
OH
O
OH
26 Chemistry 360 / Student Manual
-
4. Draw all the resonance forms for the following species:
O
O
5. Circle the secondary thiol
S
SHSH
6. Draw the mechanism showing the acid catalyzed hydration of
acetone.
O H3O+
E GGGGGGGGGGGGGGGGC
HO OH
Organic Chemistry II 27
-
7. Identify regents (a)-(c) in the following scheme:
O
OH
GGGGGGGGA
OH
GGGGGGGGA
O
H
DGGGGGGGG
(a) (b)
(c)
8. Sketch the 1H NMR spectrum of ethyl acetate:
O
O .
For each signal, indicate intensity, multiplicity and chemical
shift.
8ppm
7 6 5 4 3 2 1 0
28 Chemistry 360 / Student Manual
-
9. What properties account for the fact that acetic acid is a
stronger acidthan ethanol?
10. Compound A, C2H4O, shows an infrared absorption at 1715 cm1
and
an 1H NMR spectrum as detailed below.
Signal (ppm) Intensity Multiplicity
9.8 1 quartet
2.2 3 doublet
Propose a structure for Compound A, and justify your answer.
Organic Chemistry II 29
-
Part B: Longer Questions (marks indicated)
11. Identify the major product or products for seven (7) of the
following14 marksreactions, and show stereochemistry where
appropriate.
Note: Only the first seven questions answered will be
markedsoonly give answers for those items you want marked.
a.O
GGGGGGGGGGGGGGGA , ether1. CH3MgBr
2. H3O+
b.O
GGGGGGGGA
HCN
c.
O
GGGGGGGGGGGGA
NH2OH
30 Chemistry 360 / Student Manual
-
d.OH
GGGGGGGGGGGA
PCC
CH2Cl2
e.O
NH2
GGGGGGGGGGA
SOCl2
f.O
GGGGGGGGA
H Br
g.
O
OH
OH
GGGGGGGGGGGGGGGGGGA
O
O
O
N
Organic Chemistry II 31
-
h.SH
GGGGGGGGGGGGGGGA
l2
H2O
i. GGGGGGGGGGGGGGGGGGGA
Cl
O
O OH
j. GGGGGGGGGGGGGGGGGGGGA1. O3
2. Zn, CH3CO2H
k.O
O
OGGGGGGGGGGA
2 NH3
32 Chemistry 360 / Student Manual
-
12. Show by means of a series of chemical equations how three
(3) of the12 marksfollowing conversions could be achieved.
Note: Only the first three questions answered will be markedso
onlygive answers for those items you want marked.
a.
OH
GGGGGGGGA
O
b.OH
GGGGGGGGA
O
Organic Chemistry II 33
-
c. GGGGGGGGAO
d.O
GGGGGGGGA
OH
13. Write the complete stepwise mechanism for the reaction shown
below.8 marksShow all intermediate structures and mark electron
flows with arrows.
O
NH2GGGGGGGGBF GGGGGGGG
H3O+
O
OH+ NH+4
34 Chemistry 360 / Student Manual
-
14. Give a brief definition for three (3) of the following
terms. Use6 marksexamples where appropriate.
Note: Only the first three questions answered will be markedso
onlygive answers for those items you want marked.
a. mercapto group
b. carbinolamine
c. Fischer esterification reaction
d. thioester
e. enolate ion
f. , -unsaturated carbonyl compound
Organic Chemistry II 35
-
15. An unknown Compound A shows the molecular ion M+ at m/z 1147
marks(C7H14O), with a single major fragment at m/z 71.
The infrared spectrum of Compound A displays a strong
absorptionband at 1715 cm1, and its 1H NMR spectrum is shown
below.
Derive the structure of Compound A. Justify your answer.[7
marks]
1H NMR
ppm7 6 5 4
1H
3 2 1
6H
0
END OF EXAMINATION
36 Chemistry 360 / Student Manual
-
Sample Final Examination
The final examination is three (3) hours long. In the actual
examination, youwill not be allowed to consult your books or notes;
however, you will bepermitted to use a calculator or slide rule.
You will also be provided with aperiodic table and a set of 1H NMR
chemical shifts and infrared stretchingfrequencies.
Part A: Short Questions (3 marks each, unless otherwise
noted)
1. Provide the IUPAC name for each of the compounds below.1 mark
each
IUPAC name:
a.NH
b.
O
CN
c.
O
Cl
d.
SH
Br
e. Li Cu(CH3)2
f. NH2
Organic Chemistry II 37
-
2. Draw the IUPAC the chemical structure for each of the
compounds below.1 mark each
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 Chemistry 360 / Student Manual
-
3. Rank the basicity of the amines below (1 = least basic, 3 =
most basic)
H2N CH2CH3NH
NH2
4. Write the resonance structures for the anion below.
O O
Organic Chemistry II 39
-
5. a. What alkyl halide would you use to prepare
4-phenylbutanoic acidusing the malonic ester synthesis?
b. What alkyl halide would you use to prepare
4-phenyl-2-butanoneusing the acetoacetic ester synthesis?
6. a. What is the structure of the carboxylic acid precursor
to3-methylaniline
CH3
NH2
when prepared by the Curtius reaction?
b. Is the structure of this carboxylic acid the same as or
different from thestructure of the carboxylic acid needed to
prepare 3-methylaniline bythe Hofmann reaction?
40 Chemistry 360 / Student Manual
-
7. a. Circle the most stable stable cation
+
+
+
b. Circle the optically active compound
Cl
Cl
Br
CH3 H3C
H
Cl
CHO
C
OHH
HHO
OHH
CH2OH
H2OH
8. Draw the structure of the carbonyl compound whose 1H NMR
spectrumis summarized in the table below.
Chemical shift (ppm)
Signalmultiplicity
2.1 singlet (3 H)
2.4 quartet (2 H)
1.1 triplet (3 H)
Organic Chemistry II 41
-
Part B: Longer Questions (marks indicated)
9. State the major product or products for ten (10) of the
reactions below.20 marks
Note: Only the first ten questions answered will be markedso
onlygive answers for those items you want marked.
a. HC
HHO
OHH
CH2OH
O
GGGGGGGGGGGGGGGGA
HNO3
b.
NO2
GGGGGGGGGGGGGGGGGGGGGA
1. SnCl2, HCl
2. HNO2, H2SO43. NaI
c. CN GGGGGGGGGGGGGGGGGGGGGA
1.MgBr
2. H3O+
42 Chemistry 360 / Student Manual
-
d.
O
OH GGGGGGGGGGGGGGGGA1. Br2, PBr3
2. H2O
e.N
+
O
GGGGGGGGGGGGGGGGA
1. THF
2. H+
f.O
OH
GGGGGGGGGGGGGGGGGGGA
1. SOCl2
2. H N
g.O
O
GGGGGGGGGGGGGGGGGGGGGGGGGA
1. NaOCH3, CH3OH
2. H3O+
Organic Chemistry II 43
-
h.O
GGGGGGGGGGGGA
NH2NH2
KOH
i..
..
H
OHH
GGGGGGGGGGGGGGGGA
CrO3
H3O+
j.
OH
O
OH
GGGGGGGGGGGGGGGGGGGGGGGA
1.
O
Clpyridine
2. CH3OH, HCl
44 Chemistry 360 / Student Manual
-
k.
O
GGGGGGGGGGGGGGGGGGGGGGGA
NaOCH3, CH3OH
l.SH
GGGGGGGGGGGGGGA
l2
H2O
m. O + (C6H5)3P+
C
H CH3 GGGGGGGGGGGGGGAOO
n.
OH
OH GGGGGGGGGGGGGGAPCC
CH2Cl2
Organic Chemistry II 45
-
10. In your own words, define five (5) of the terms given
below.10 marks
Note: Only the first five questions answered will be markedso
onlygive answers for those items you want marked.
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 Chemistry 360 / Student Manual
-
11. Propose the step-wise mechanism for each of the
transformations10 marksbelow. Use arrows to show electron flow
where appropriate.
a.
N N+
HSO4
+
NH2
GGGGGGGGA
N N
NH2
b. O
H
GGGGGGGGGGGGGGAD GGGGGGGGGGGGGG
NaOH
ethanol
OH O
H
Organic Chemistry II 47
-
12. Propose and show the synthetic pathway for two of the10
markstransformations below.
Note: Only the first two questions answered will be markedso
onlygive answers for those items you want marked.
a.
CN
GGGGGGGGA
NH2
b.
O
GGGGGGGGA
HO
O
c.
O O
OGGGGGGGGA
O
48 Chemistry 360 / Student Manual
-
13. a. Compound A, C10H18O undergoes reaction with dilute H2SO4
at10 marks25C to yield two alkenes, C10H16, B and C. The major
alkeneproduct B gives only cyclopentanone after ozone
treatmentfollowed by reduction with zinc in acetic acid.
Identify A, B and C.
b. Compound A is a D-aldopentose C5H10O5 that can be oxidized
toan optically inactive aldaric acid B on treatment with HNO3.
On Kiliani-Fischer chain extension, Compound A is converted
tocompounds C and D: Compound C can be oxidized to an
opticallyactive aldaric acid E, where as Compound D is oxidized to
anoptically inactive aldaric acid F.
What are the structures of A to F?
Organic Chemistry II 49
-
Note: The remainder of this examination is based on the three
optional unitsin this course. You have studied one of the possible
three units. Pleasecomplete only one (1) of the following
questions
Unit 26 Biomolecules: Amino Acids, Peptides and Protein
15. Threonine, (2S, 3R)-2-amino-3-hydroxybutanoic acid, has two
chirality10 markscentres.
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
acidphenylalanine beginning with diethyl acetamidomalonate.
50 Chemistry 360 / Student Manual
-
Unit 27 Biomolecules: Lipids
16. a. Draw the major products you would expect from the
reaction of10 markscholesterol and the following reagents
HOCholesterol
i.GGGGGGGGGGGGGGA
CrO3
H+
ii.
GGGGGGGGGGGGGGGGGGGA
O
O
O
pyridine
iii.GGGGGGGGGGGGGGA
Br2
CH2Cl2
Organic Chemistry II 51
-
b. Draw the molecules below in chair conformations, and
indicatewhether the bridgehead methyl is axial or equatorial.
i.
.
H
ii.
H
52 Chemistry 360 / Student Manual
-
Unit 28 Biomolecules: Nucleic Acids
17. a. Describe, using chemical structures, two major structural
differences10 marksbetween 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
sequencebelow?
(5) G A T T A C C G T A(3) end
END OF EXAMINATION
Organic Chemistry II 53
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54 Chemistry 360 / Student Manual
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Sample Examination Answer Keys
Organic Chemistry II 55
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56 Chemistry 360 / Student Manual
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Sample Midterm Examination
Part A:
1. Provide the IUPAC name for each of the compounds below.
Indicatestereochemistry as appropriate.
IUPAC name:
a. O
O
cyclopentyl 2-methylpropanoate
b.
O
1-methoxycyclohexene
SHH
.c. (R)3-heptanethiol
Organic Chemistry II 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
HOCN
3. Rank the acidity of the compounds below (1 = most acidic; 3 =
leastacidic).
O
OHO
OH
O
OH
3 2 1
58 Chemistry 360 / Student Manual
-
4. Draw all the resonance forms for the following species:
O O
O
O
O O
5. Circle the secondary thiol
S
SHSH
6. Draw the mechanism showing the acid catalyzed hydration of
acetone.
OH
O
HH
+
E GGGGGGGGGGGGGGGGC
H3O+
H2O
HO OH
H2O +
EGGGGGG
GGGGGGC
+OHGGGBF GGG
O+H H
OH
GGGBF GGG
OH
OH
+ H3O+
HO
H
Organic Chemistry II 59
-
7. Identify regents (a)-(c) in the following scheme:
O
OH
LiAlH4GGGGGGGGGGGGA
ether OH
PCCGGGGGGGGGA
CH2Cl2
O
H
NH2 N
H2
GGGGGGGGGGGGGGA
KOH
8. Sketch the 1H NMR spectrum of ethyl acetate:
O
O .
For each signal, indicate intensity, multiplicity and chemical
shift.
8ppm
7 6 5 4 3 2 1 0
~3.5 ppm
OCH2
2H
CH3
3H
O
CH3C
3H
~2.0 ppm ~1.0 ppm
60 Chemistry 360 / Student Manual
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9. What properties account for the fact that acetic acid is a
stronger acidthan ethanol?
O
OH
GGGGGGBF GGGGGG
O
O
O
O
OH GGGGGGBF GGGGGG O
Resonance stabilization of carboxylate anion accounts for
increasedacidity of acetic acid compared to ethanol.
10. Compound A, C2H4O, shows an infrared absorption at 1715 cm1
and
an 1H NMR spectrum as detailed below.
Signal (ppm) Intensity Multiplicity
9.8 1 quartet
2.2 3 doublet
Propose a structure for Compound A, and justify your answer.
d 2.2 ppm
degrees of unsaturation = 1
1715 cm1
H3CC
O
H
q 9.8 ppm
Organic Chemistry II 61
-
Part B: Longer Questions
11. Identify the major product or products for seven (7) of the
followingreactions, and show stereochemistry where appropriate.
Note: Only the first seven questions answered will be
markedsoonly give answers for those items you want marked.
a.O
GGGGGGGGGGGGGGGA either1. CH3MgBr
2. H3O+ OH
or
b.O HCN
GGGGGGGGGA
NC OH
c.
O
GGGGGGGGGGGGA
NH2OH
NOH
62 Chemistry 360 / Student Manual
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d.OH
GGGGGGGGGGGA
PCC
CH2Cl2
O
H
e.O
NH2
GGGGGGGGGGA
SOCl2 CN
f.O
GGGGGGGGA
H Br OH
Br
g.
O
OH
OH
GGGGGGGGGGGGGGGGGGA
O
O
O
N
O
OH
O
O
Organic Chemistry II 63
-
h.SH
GGGGGGGGGGGGGGGA
l2
H2OS S
i. GGGGGGGGGGGGGGGGGGGA
Cl
O
O OH
O
j. GGGGGGGGGGGGGGGGGGGGA1. O3
2. Zn, CH3CO2HO +
H
O
k.O
O
OGGGGGGGGGGA
2 NH3O
NH2
+
O
ONH+4
64 Chemistry 360 / Student Manual
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12. Show by means of a series of chemical equations how three
(3) of thefollowing conversions could be achieved.
Note: Only the first three questions answered will be markedso
onlygive answers for those items you want marked.
a. OH
CrO
3DGGGGGGGGG
D GGGGGGGGGGG
pyridine
GGGGGGGGGGGGGA
O
OBr2/PBr3
GGGGGGGGGGGGGGA
OBr
b.OH
GGGGGGGGA
O
O
GGGGGGGGGGGANaOHethanol
O
H O
H3O+
GGGGGGGGGGA
CrO
3DGGGGGGGGGGGGGGG
H3O+,acetone
Organic Chemistry II 65
-
c.Eith
er
GGGGGGGGGGGA
O
CH3ClD GGGGGGGGGGG
AlCl3
GGGGGGGGGGGA
NBS
CH2 C
l2
Br
Na OCH3GGGGGGGGGGGGGGGA
CH3OH
+
or
GGGGGGGGGGGA
O
CH3ClD GGGGGGGGGGG
AlCl3
KMnO4D GGGGGGGGGGGG
CO2 H
GGGGGGGGGGGA
LiAlH
4
ether
OH
1. NaOHGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGGA
2. CH3Br
66Chem
istry360
/StudentManual
-
d.O
GGGGGGGGGGGA
OH
Br
DGGGGGGGGGGGGGGGGGGGGGG
PPh3
BH3
GGGGGGGGGGGGGGGGGGGGGGA
H2O2, O
H
13. Write the complete stepwise mechanism for the reaction shown
below.Show all intermediate structures and mark electron flows with
arrows.
O
NH2
GGGGGGBF GGGGGG
H3O+
O
OH+ NH+4
H O
H
H
+
GGGGGGGGB
FGGGGGGGG
+HO
H
HO+
NH2GGGGGGBF GGGGGG
OH
OHH
NH2
+
GGGGGGBF GGGGGG
GGGGGGGGGGGGGGGGGGGGGGGGB
FGGGGGGGGGGGGGGGGGGGGGGGG
OH
OH
NH3+
Organic Chemistry II 67
-
14. Give a brief definition for three (3) of the following
terms. Useexamples where appropriate.
Note: Only the first three questions answered will be markedso
onlygive answers for those items you want marked.
a. mercapto group
a thiol SH
b. carbinolamine
COH
NH2
c. Fischer esterification reaction
an acid catalyzed reaction between a carboxylic acid and an
alcohol
R C
O
OH + ROHH+
GGGGGGBF GGGGGG R C
O
OR + H2O
d. thioester
O
SR
e. enolate ion
O
f. , -unsaturated carbonyl compound
O
68 Chemistry 360 / Student Manual
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15. An unknown Compound A shows the molecular ion M+ at m/z
114(C7H14O), with a single major fragment at m/z 71 in its mass
spectrum.
The infrared spectrum of Compound A displays a strong
absorptionband at 1715 cm1, and its 1H NMR spectrum is shown
below.
Derive the structure of Compound A. Justify your answer.
1H NMR
ppm7 6 5 4
1H
3 2 1
6H
0
degree of unsaturation = 1
1715 cm1 C = O
NMR C
CH3
CH3
H
14H 7H = 7H; therefore, the molecule is symmetrical.
MS C
O
CH
CH3
CH3
major fragment
m/z 28
m/z 43
m/z 71
Compound A:
H3C
CH
H3C
C
O
C H
CH3
CH3
END OF EXAMINATION
Organic Chemistry II 69
-
70 Chemistry 360 / Student Manual
-
Sample Final Examination
The final examination is three (3) hours long. In the actual
examination, youwill not be allowed to consult your books or notes;
however, you will bepermitted to use a calculator or slide rule.
You will also be provided with aperiodic table and a set of 1H NMR
chemical shifts and infrared stretchingfrequencies.
Part A:
1. Provide the IUPAC name for each of the compounds below.
IUPAC name:
a.NH
pyrrolidine
b.
O
CN
3-cyano-2-cyclohexen-1-one
c.
O
Cl 2-chlorocyclopentanone
d.
SH
Br
4-bromobenzenethiol
e. Li Cu(CH3)2 lithium dimethylcuprate
f. NH2 aniline
Organic Chemistry II 71
-
2. Draw the IUPAC the chemical structure for each of the
compounds below.
a. D-glyceraldehyde
CH O
H OH
CH2OH
b. N,N-dimethyl cyclopentylamine
N
c. (S) 4-bromo-2-hexanone
H
OBr
d. 2-ethylcyclohexane-1,3-dione
O
O
e. 2-butene-1-thiol
SH
f. 3-chloropyridine
Cl
N
72 Chemistry 360 / Student Manual
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3. Rank the basicity of the amines below (1 = least basic, 3 =
most basic)
H2N CH2CH3NH
NH2
3 2 1
4. Write the resonance structures for the anion below.
O O
O O
O O
O O
There are three resonance structures.
Organic Chemistry II 73
-
5. a. What alkyl halide would you use to prepare
4-phenylbutanoic acidusing the malonic ester synthesis?
Br
+ CH2(CO2R)2
b. What alkyl halide would you use to prepare
4-phenyl-2-butanoneusing the acetoacetic ester synthesis?
Br+
ORC
O
O
6. a. What is the structure of the carboxylic acid precursor
to3-methylaniline
CH3
NH2
when prepared by the Curtius reaction?
CH3
CO2H
b. Is the structure of this carboxylic acid the same as or
different from thestructure of the carboxylic acid needed to
prepare 3-methylaniline bythe Hofmann reaction?
It is the same.
74 Chemistry 360 / Student Manual
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7. a. Circle the most stable stable cation
+
+
+
1 2 2, allylic
b. Circle the optically active compound
Cl
Cl
Br
CH3 H3C
H
Cl
CHO
C
OHH
HHO
OHH
CH2OH
H2OH
8. Draw the structure of the carbonyl compound whose 1H NMR
spectrumis summarized in the table below.
Chemical shift (ppm)
Signalmultiplicity
2.1 singlet (3 H)
2.4 quartet (2 H)
1.1 triplet (3 H)
O
Organic Chemistry II 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
onlygive answers for those items you want marked.
a. HC
HHO
OHH
CH2OH
O
GGGGGGGGGGGGGGGGA
HNO3
CO2H
HHO
OHH
CO2H
b.
NO2
GGGGGGGGGGGGGGGGGGGGGA
1. SnCl2, HCl
2. HNO2, H2SO43. Nal
N N+
HSO4
GGGA
I
c.CN GGGGGGGGGGGGGGGGGGGGGA
1.MgBr
2. H3O+
O
76 Chemistry 360 / Student Manual
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d. O
OH GGGGGGGGGGGGGGGA1. Br2, PBr3
2. H2OBr
O
OH
e.N
+
O
GGGGGGGGGGA
1. THF
2. H+
O O
f.O
OH
GGGGGGGGGGGGGGGGGGGA
1. SOCl2
2. H N
O
N
g.O
O
GGGGGGGGGGGGGGGGGGGGGGGGGA
1. NaOCH3, CH3OH
2. H3O+
O
OH
GGGGGGGGGGGA
O
Organic Chemistry II 77
-
h.O
GGGGGGGGGGGGA
NH2NH2
KOH
i..
..
H
OHH
GGGGGGGGGGGGGGGGA
CrO3
H3O+
O
.
.
H
H
j.
OH
O
OH
GGGGGGGGGGGGGGGGGGGGGGGA
1.
O
Clpyridine
2. CH3OH, HCl
O
O
O
O
78 Chemistry 360 / Student Manual
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k.
O
GGGGGGGGGGGGGGGGGGGGGGGA
NaOCH3, CH3OH .
OH
OCH3
l.SH
GGGGGGGGGGGGGGA
l2
H2OS S
m.O + (C6H5)3P
+
C
H CH3
GGGGGGGGGGA OO
CHCH3
n.
OH
OH GGGGGGGGGGGGAPCC
CH2Cl2
O
O
H
Organic Chemistry II 79
-
10. In your own words, define five (5) of the terms given
below.
Note: Only the first five questions answered will be markedso
onlygive answers for those items you want marked.
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
isdissolved in water; it is caused by reversible opening and
closing ofthe hemiacetal, which gives a mixture of anomers
c. chemical shift
the position in a 1H NMR spectrum where a nucleus absorbs
d. parent peak
the peak in the mass spectrum corresponding to the molecularion,
M+
e. enol
a vinyl alcohol, OH
f. anomers
cyclic stereoisomers of sugars that differ only in their
configurationat the hemiacetal (anomeric) carbon
g. Hell Volhard-Zelinskii reaction
formation of an -bromo carboxylic acid
RCH2CO2H GGGGGGGGGGA1. Br2
PBr32. H2O
RC
Br
HCO2H
h. mixed aldol
aldol reaction between one or more aldehydes and one or
moreketones, one of which has no H and thus cannot form anenolate
ion
i. ,-unsaturated ester
O
OR
80 Chemistry 360 / Student Manual
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11. Propose the step-wise mechanism for each of the
transformationsbelow. Use arrows to show electron flow where
appropriate.
a.
N N+
HSO4
+
NH2
GGGGGGGGA
N N
NH2
DGGGGGGGGGGGGGGGGGGG
N N NH2+ H2SO4
+
H HSO4
b.
OH
H
O
H
!
GGGGGGGGGGGGGGAD GGGGGGGGGGGGGG
ethanol
NaOH OH O
H
O
H
HO
H
O
H
EGGGGGGGG
GGGGGGGGC
+
GGGGGGGGGGBF GGGGGGGGGG
H2O
H
OH
O
H+ OH
Organic Chemistry II 81
-
12. Propose and show the synthetic pathway for two of
thetransformations below.
Note: Only the first two questions answered will be markedso
onlygive answers for those items you want marked.
a. Either
CN
GGGGGGGGA
NH2
O
OH
1.NaO
HDGGGGGGGGGGGGGG
2.H3O+
GGGGGGGGGGGGGGASOCl2
O
Cl
1.NaN
3GGGGGGGGGGGGGGGGA
2.H2O/
or
CN
GGGGGGGGA
NH2
O
OH
1.NaO
HDGGGGGGGGGGGGGG
2.H3O+
GGGGGGGGGGGGGGASOCl2
O
Cl
1.NH3
GGGGGGGGGGGGGGGGGGGA
2.Br 2/NaO
H
H2O
82 Chemistry 360 / Student Manual
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b. O
GGGGGGGGGGGGGGGGA
HO
O
O2N
O
1.HNO3,H
2SO
4DGGGGGGGGGGGGGGGGGGGGGGG
GGGGGGGGGGGGGGGGGGGGA
1. SnCl2/HCl
2. HNO2/H2SO4
N N
O+
Cu2O/Cu(N
O3) 2/H2O
GGGGGGGGGGGGGGGGGGGGGGGGGGGGGGA
HSO4
c.O O
OGGGGGGGGA
O
product
O
CO OEt
1.NaO
Et/EtO
HDGGGGGGGGGGGGGGGGGGGGGGG
2.Br
GGGGGGGGGGGA
1. H3O+
2. heatproduct + CO2 + EtOH
Organic Chemistry II 83
-
13. a. Compound A, C10H18O undergoes reaction with dilute H2SO4
at25C to yield two alkenes, C10H16, B and C. The major
alkeneproduct B gives only cyclopentanone after ozone
treatmentfollowed by reduction with zinc in acetic acid.
Identify A, B and C.
degree ofunsaturation = 2
C10H18OA GGGGGGGGGGGGA
dil H2SO4 BC10H16degree of
unsaturation = 3
+ CC10H16
O3
DGGGGGGGGG
2n/HoAc
O
B is
A must beOH
and C should be
84 Chemistry 360 / Student Manual
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b. Compound A is a D-aldopentose C5H10O5 that can be oxidized
toan optically inactive aldaric acid B on treatment with HNO3.
On Kiliani-Fischer chain extension, Compound A is converted
tocompounds C and D: Compound C can be oxidized to an
opticallyactive aldaric acid E, where as Compound D is oxidized to
anoptically inactive aldaric acid F.
What are the structures of A to F?
A
OH
OH
OH
CH2OH
CHO
GGGGGGA
Kiliani
FischerC
OH
OH
OH
OH
CH2OH
CHO
+ D
HO
OH
OH
OH
CH2OH
CHO
HNO3
DGGGGGGGGGGG
HNO3
DGGGGGGGGGGG
HNO3
DGGGGGGGGGGG
B
OH
OH
OH
CO2H
CO2H
E
HO
OH
OH
OH
CO2H
CO2H
opticallyactive
F
OH
OH
OH
OH
CO2H
CO2H
opticallyinactive
Therefore,
D is
OH
OH
OH
OH
CH2OH
CHO
F is
OH
OH
OH
OH
CO2H
CO2H
Organic Chemistry II 85
-
C is
HO
OH
OH
OH
CH2OH
CHO
E is
HO
OH
OH
OH
CO2H
CO2H
A is
OH
OH
OH
CH2OH
CHO
B is
OH
OH
OH
CO2H
CO2H
86 Chemistry 360 / Student Manual
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Note: The remainder of this examination is based on the three
optional unitsin this course. You have studied one of the possible
three units. Pleasecomplete only one (1) of the following
questions
Unit 26 Biomolecules: Amino Acids, Peptides and Protein
15. Threonine, (2S, 3R)-2-amino-3-hydroxybutanoic acid, has two
chiralitycentres.
a. Draw the Fischer projection of threonine
SH2N
OHR
CH3
CO2H
b. Draw the predominant form of threonine in a pH 4.0 buffer
solution.The isoelectric point of threonine is 5.6.
HO H
H2N H
O
O
.
.
c. Use the amidomalonate synthesis to prepare the amino
acidphenylalanine beginning with diethyl acetamido malonate.
O
CCH3HN
CH CO2Et
CO2Et
GGGGGGGGGGGGA
1. NaOEt
2. PhCH2BrPhCH2 C
CO2Et
HN
CO2Et
O
GGGGGGGA
H3O+
heatPhCH2 CH CO
2
+NH3
Organic Chemistry II 87
-
Unit 27 Biomolecules: Lipids
16. a. Draw the major products you would expect from the
reaction ofcholesterol and the following reagents
HOcholesterol
i. GGGGGGGGGGGGGGACrO3
H+
O
ii. GGGGGGGGGGGGGGGGGGGA
O
O
O
pyridineO
O
iii. GGGGGGGGGGGGGGABr2
CH2Cl2
HO
.
BrBr
88 Chemistry 360 / Student Manual
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b. Draw the molecules below in chair conformations, and
indicatewhether the bridgehead methyl is axial or equatorial.
i.
.
H
H
axial CH3 group
ii.
H
H
axial CH3 group
Organic Chemistry II 89
-
Unit 28 Biomolecules: Nucleic Acids
17. a. Describe, using chemical structures, two major structural
differencesbetween DNA and RNA.
O
PO
O
deoxyriboseDNA
OCH2O
HO
base
O
NH
ON
sugar
thymineunique base
O P
O
O
OCH2O
OH OH
base
riboseRNA
O
NH
ON
sugar
uracilunique base
b. Explain each of the following terms:
i. replication
process by which double-stranded DNA uncoils and is replicated
toproduce two new copies
ii. messenger RNA
During transcription, a short segment of the DNA double
helixrewinds and complementary RNA line up to produce mRNA, aform
of RNA that carries genetic messages to ribosomes, the cellpart
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
sequencebelow?
(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 Chemistry 360 / Student Manual