Syllabus - Admissions



Syllabus

Marshall University, College of Science

Chemistry 327

Section 101

Introductory Organic Chemistry

Fall 2018

3 Credit Hours

Instructor:

 

| |

|Dr. Robert J. Morgan |  |

|Department of Chemistry  |E-mail:     morganr@marshall.edu |

|Marshall University  |Office: S-486 |

|Huntington, WV   25755 |Phone: 304-696-3159 |

| |Office : M(S486) 1-2, W(S455) 1-2, TR 2-3 |

| | |

| | |

Prerequisites: Chemistry 212. 

Course Description:

CHM 327 is a:

1. One semester survey of organic chemistry emphasizing structure, nomenclature, and reactivity.

2. Students who have been away from chemistry for a while, and would like a preview/review of Organic Chemistry I&2

3. Anyone who feels uncomfortable entering Organic Chemistry I.

4. Anyone who needs a refresher course in Organic Chemistry I, including those taking entry exams (MCAT, teaching etc.).

Course will close: December 13, 2018 @ 6:00 pm (EST). See below for details.

Required Materials:

Required:

Hart Craine/Hart/Hadad, organic Chemistry, A Short Course 13th ed. Cengage Learning ISBN-10: 1111425566​

online from the Marshall University Bookstore or they will take phone orders at 304-696-2461.

Reccomended: Study Guide with Solutions Manual for Hart/Craine/Hart/Hadad's Organic Chemistry: A Short Course, 13th, Edition ISBN-13: 978-1111425852 | ISBN-10: 111142585X

(This work is licensed under a Creative Commons License. Virtual Text of Organic Chemistry 1999. An interactive textbook covering the usual topics treated in a college sophomore-level course. Links are offered to advanced discussions of selected topics.)

Molecular Models:  If you have a hard time visualizing some of the three-dimensional aspects you may want to purchase an inexpensive set of molecular models but I would recommend that you not pay more than about $15.  And, I would suggest that you wait until you find that you really need them before buying them.

Attendance Policy:

This course is delivered online and requires not attendance in the traditional sense. The course is self-paced and has only has one deadline. You must take the final exam by the given deadline December 13, 2018 @ 6:00 pm (EST). At that time I will close the course and I will accept no further work.

By enrolling in this course, you agree to the University Policies listed below. (Admittedly some are silly as applied to an online course)Please read the full text of each policy be going to marshall.edu/academic-affairs and clicking on “Marshall University Policies.” Or, you can access the policies directly by going to

Academic Dishonesty/ Excused Absence Policy for Undergraduates/ Computing Services Acceptable Use/ Inclement Weather/ Dead Week/ Students with Disabilities/ Academic Forgiveness/ Academic Probation and Suspension/ Academic Rights and Responsibilities of Students/ Affirmative Action/ Sexual Harassment

Policy for Students with Disabilities:

Marshall University is committed to equal opportunity in education for all students, including those with physical, learning and psychological disabilities. University policy states that it is the responsibility of students with disabilities to contact the Office of Disabled Student Services (DSS) in Prichard Hall 117, phone 304 696-2271 to provide documentation of their disability. Following this, the DSS Coordinator will send a letter to each of the student’s instructors outlining the academic accommodation he/she will need to ensure equality in classroom experiences, outside assignment, testing and grading. The instructor and student will meet to discuss how the accommodation(s) requested will be provided. For more information, please visit or contact Disabled Student Services Office at Prichard Hall 11, phone 304-696-2271.

Note for students with visual impairments: This course contains a substantial number of graphics files that cannot be adequately described as text equivalents. If you contact the instructor arrangements can be made to provide the source files for the graphics and/or Braille embossed high resolution graphics.

Since this syllabus is rather long, I have included some hyperlinks to help you find specific information.

University Policies:

Academic Honesty and Plagiarism:

University policy states that any act of a dishonorable nature which gives the student engaged in it an unfair advantage over others engaged in the same or similar course of study is prohibited. You must do you own work inside and outside of this class. Cheating/plagiarism in or out of this class is prohibited.

You will be given a final grade of F for any instance of academic dishonesty. I am happy to assist you with anything you do not understand or have questions about. Cheating in this course includes, but is not

limited to:

l. Recording identical answers and screen captures as a classmate for your assignments.

lI. Plagiarizing material from the textbook or readings. To avoid plagiarism, read all assigned material first; complete your exercises second; then base your written answers to review questions on your experience; only refer to the textbook or readings as necessary.

Required Materials

Computer and Software Requirements

Contacting the Instructor

Course Objectives

How This Course Is Organized

List of Topics to Be Covered

Time Requirement

Target Dates and Deadlines

Grading Policies

Instructor Biographical Information

 

Required Materials:

TEXT:

Hart Craine/Hart/Hadad, organic Chemistry, A Short Course 13th ed. Cengage Learning ISBN-10: 1111425566​

online from the Marshall University Bookstore or they will take phone orders at 304-696-2461.

(This work is licensed under a Creative Commons License. Virtual Text of Organic Chemistry 1999. An interactive textbook covering the usual topics treated in a college sophomore-level course. Links are offered to advanced discussions of selected topics.)

Molecular Models:  If you have a hard time visualizing some of the three-dimensional aspects you may want to purchase an inexpensive set of molecular models but I would recommend that you not pay more than about $15.  And, I would suggest that you wait until you find that you really need them before buying them.

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Computer and Software Requirements:

• For a list of current requirements for the course please see Basic ECourse requirements and information

• You will need ready access to the internet.  Home access is highly recommended. Your computer should meet the minimum requirements listed here here and also have the required plug-ins. Plug in check

• Broadband access such as DSL or cable modem. Stating with Bb 9.1, Dial-up appears to too slow to be useful.

• You will also need the Sun Virtual Java Machine and you can download that from the download page

• Be sure to run the browser tuneup to make sure that you have all the correct browser settings. Note well that it is very important to have the correct cache settings for your browser.  If the cache is not set properly you may have problems accessing portions of the course. 

• If you have technical problems, please go to the

Help desk

• HELP DESK PHONE NUMBERS:

(304) 696-3200 (Huntington, WV)

(304) 746-1969 (Charleston, WV)

(877) 689-8638 (Toll free)

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Contacting the Instructor:

How to ask a question.

I find that if I tell students specifically what to do. They will ask more questions. Quiz questions and Exam questions are by far the most common questions I get. The quizzes are for learning so use them for that. The best questions are "I got question 4 on quiz #3, 5th attempt wrong! What did I do wrong? That's all I need.

quiz or exam#

question #

Attempt #.

You can take a screen shot if you want etc. but I don't need it.

Whenever you need help with the course or just want to ask a question about anything, you should feel free to contact me. I am a full time professor in the Chemistry Department at Marshall University. I have an office on the fourth floor of the Science building at the Huntington Campus.

The best method for contacting me is by e-mail. I tend to check my email all day long on regular class days (less frequent in the summer). Do not use the internal Bb messaging system. Send me an email. I tend to reply to e-mail as I receive it. I usually check e-mail in the evenings, just keep in mind that I probably cannot fix Bb related problems until the next weekday.   On weekends or evenings you can CC: your message to rjm8008@. (Especially if you believe the Marshall servers are down) I will normally respond by whichever method you used to send your message.  If you do not receive a response to an e-mail message within 48 hours you should assume that either your original message or my reply has gone astray in the e-mail system and you should resend the message.  Don’t feel you are “nagging me” I’m there to answer your questions.

Please note that while we tend to think of e-mail as being a nearly instantaneous means of communication there are times that there are significant delays in e-mail transmissions.  Under certain circumstances it has been known to take as much as 48 hours for an e-mail message to get between a Marshall University account and an account at a local internet service provider. 

I will establish an e-mail list that will be used to make general announcements.  Your Marshall University e-mail account will automatically be placed on this list. 

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Purpose of the Course

The purpose of the course is no give the student a general knowledge of organic chemistry. The course presents a survey of the important topics that will be encountered during a year of sophomore organic chemistry, but without the details required by professionals and science majors. The content in the course should be sufficient. The course is designed to meet the needs of majors in the fields of education, lab sciences, clinical technology, dietetics and even certain areas of biology and geology.

Structure of the Course

The course contains 43 quizzes, 3 exams and a final exam. You progress through the course by taking and making 80% on each quiz. When you pass a quiz the next one appears. After several quizzes, an exam will appear, after you take the exam the next module will appear and you progress through it the same way. Following completion of all three modules will allow you to take the final exam, and thereby completing the course.

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Using the Course Materials

This course is strongly based on the included lecture notes and the Hart text. My aim in the lecture notes is not to teach you all of Organic Chemistry, but rather help you to build problem solving skills necessary in the course chemistry.

Before taking a quiz:

A. Look through the ‘contents’ file in each section of a module

B. Read the lecture notes contained in the section.

C. Read the sections in Hart, and do the assigned problems.

Finally, I can also be a useful component of the course. Send me your questions and I can help you fill in the cracks that the other course materials may leave.

Organization of the Course:

Chemistry is a subject that builds on a foundation.  You cannot understand the later topics unless you understand the earlier topics.  You cannot go on to a new topic until you have mastered the current one.  This is especially true of organic chemistry. Having a poor understanding of the early topics will haunt you throughout the course. To prevent this I stop you at the end of each topic and give you one or more quizzes. You must make 80% (or higher) to go on to the next part of the course (quiz, exam or Learning module). Only the highest score on a quiz will count so you can never lower your grade by re-taking a quiz. Additionally, you may take the quiz as many times as you wish. The only requirement is that you may be required to wait a few minutes between each attempt. The quizzes are timed, but allow a generous amount of time to complete

When you first start the course, only one topic will be available to you.  Whenever you complete a topic, a new one will become available.  All of the older ones will stay available so that you can review them as needed.

I have divided the course into 41 units, with 43 quizzes. – Each Unit is about the size of an hour lecture in a regular B&M organic chemistry course, although a few units are longer and a few are shorter. Each unit will have one or two quizzes associated with it. You should be able to complete some topics in a few minutes but some will take more effort.

More on the quizzes, exams and final…

The course is divided into three roughly equal sized parts.  There is an hour exam after you complete each of these parts.  Each of these parts is about the size of one lecture exam in an Organic chemistry course. Click here for a detailed list of the topics.

The quizzes are your main learning vehicle. They have between 5 and 10 questions. Your object is not to get the questions correct! Your object is to figure out why you are getting questions wrong!

The exams are longer, and are based on the quizzes. The final is based on the exams. Hint: There is only one bank of questions!

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Time Requirement

NOTE WELL:  In a normal classroom setting for this course you would be expected to attend approximately 45 hours of lectures. You would also be expected to spend roughly double that amount of time studying for the course outside of class.  The e-course format does not work magic -- you should expect to spend at least the same number of hours completing this course.  Do not put off working on the course and then expect to be able to complete it in a couple of days.  The deadline for finishing the course is December 13, 2018 @ 6:00 pm (EST). On the day of December 13th, the final will be available for you. The course will then close and no more work will be counted toward your grade. Should this date, or anything else associated with the course change, you will be notified well in advance by your University email account.

Pace of the Course

Your major objective is to finish the course on time. It's that simple. In the past students in my other online organic chemistry courses have finished a month early and be done. Others procrastinate until the last few days and finish at the deadline. Some, albeit a minority, run out of time. If you wait until the last minute and run out of time you will not receive additional time, you will be graded on what you finish. I can also say that the students who pace themselves and do a little at a time, rather than cramming at the end do better. As a matter of style, I do not push you along, I believe that an online course should be as flexible as possible; you work on it when you have time. You are responsible for pacing yourself, so don't expect friendly reminders when I think you're behind. You may get one and you may not. You can of course ask.

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Due Dates:

While the only due date is to take the final exam on the indicated date. Below is a sample schedule you can use to test your progress in the course:

Week # Completed

3 Through Quiz 3.4(15 quizzes) Exam 1

6 Through Quiz 6.4 (26 quizzes) Exam 2

9 Through Quiz 9.4 (33 quizzes) Exam 3

14 Through Quiz 11.3 (43 quizzes) Exam 4, Final Exam

Deadlines:

There is only one deadline: the day of the final exam. The rest of the course is self paced. You progress through the course by passing (80% on each), and complete three exams. This qualifies you to take the final exam and complete the course.

Grading Policy:

There will be three hour exams and a final exam in addition to the quizzes. 

There is a total of 1000 points available in the course.

Exams(3, 130 points each)) 390 points

Quizzes(43, 10 points each) 430 points

Final exam 180 points

Total 1000 points

Letter grades will be then be assigned based on the following scale for your average.

•  Greater than 830 points = A

•  Between 750-829 points = B

•  Between 650-749 points = C

•  Between 550-649 points = D

•  Less than 550 points = F

       The hour exams will be given online. There is a time limit on the exams and it will be enforced by the computer -- no answers will be accepted after the time limit on an exam.  You will get the graded exam back with your score and feedback on your errors.  Exams are closed book, closed notes. You are on your honor to take the exams without any assistance and without referring to any materials other than a basic periodic table. The final exam will be handled the same way as the hour exams. You only get one attempt on each exam. The quizzes are all taken online and the scores and the correct answers are available to you as soon as you complete the quiz

Missed exams, quizzes and Final exam policy

For each item in the course you fail to complete you will receive 0 points.

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Finally, my object is to have a typo-free- error free course. There are over 3000 questions and many pages of lecture notes. Please email me any errors you find so I can correct them. I may develop a system to reward you for finding typos. This is a new course and there will be quite a few glitches. I don't usually re-grade your quizzes if you find errors because you can take them over and over again. I do however hand grade all your wrong answers on exams and the final.

Please help me continue the hunt for problems by emailing me anything you think is an error or is causing you a problem.

Biographical Information:

 I received my B.S. in Chemistry from Queens College, and completed my Ph.D. at The City University of New York in 1992.  My dissertation research was in the area of the synthesis of Ru(II) based photocatalysts. I also taught for four years at Long Island University, before joining the Marshall University faculty in 1997.  I have taught a wide variety of courses at LIU and MU including instrumental analysis, and all levels of organic chemistry. I have taught Organic Chemistry I at a total of four Universities, and have taught this course in the classroom three times.

My research interests are currently in synthesis of ligands and development of fluorescent dyes, for which I hold two Patents. 

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 Structure of the Course

Modules for Exam I

Chapter 1. Bonding and isomerism

1.1 Bonding, Valence and Lewis structures

1.2 Formula writing and isomerism

1.3 Formal charges, Resonance and Arrow formalism

1.4 bonding and orbitals

1.5 Classification

Chapter 2. Alkanes and Cycloalkanes

2.1 Structure and properties of Alkanes

2.2 Alkyl groups

2.3 The IUPAC system

2.4 Conformations of alkanes and cycloalkanes

2.5. Reactions of alkanes

Chapter 3. Alkenes and alkynes

3.1. Nomenclature of alkenes and alkynes

3.2. Structure and bonding in alkenes and alkynes

3.3. Reactions of alkenes

3.4. Reactions of alkynes

Exam I

Modules for Exam II

Chapter 4 Aromatic Compounds

4.1 introduction and Nomenclature

4.2 Electophillic aromatic substitution

4.3 Disubstituted benzenes

4.4 Synthesis

Chapter 5. Stereoisomerism

5.1. Stereoisomers priorizing and EZ

5.2. Steroisomers Nomenclature RS

5.3 Multiple stereocenters

Chapter 6. Organic Halogen Compounds

6.1 substitution reactions

6.2 The SN2 mechanism

6.3 The SN1 mechanism

6.4 Elimination reactions and SN1 Vs SN2 repeatable online quizzes

Exam II

Modules for Exam III

Chapter 7 Alcohols, phenols and thiols

7.1 Properties of alcohols and phenols

7.2 Alcohol Nomenclature

7.3 Reactions of alcohols and phenols

Chapter 8 ethers and epoxides

8.1 Ether Nomenclature

8.2 Reactions of ethers

Chapter 9. Aldehydes and ketones

9.1 Nomenclature of aldehydes and ketones

9.2 Properties, preparation and bonding

9.3 Addition of oxygen and nitrogen nucleophiles

9.4 addition of carbon nucleophiles

Exam III

Modules for Exam IV

Chapter 10. Carboxylic Acids and Their Derivatives

10.1 Nomenclature of carboxylic acids

10.2 Nomenclature of Carboxylate derivatives

10.3 Properties of Carboxylic acids

10.4 Preparation and reactions of Carboxylic acids

10.5. Reactions of Carboxylate derivatives

Chapter 11. Amines and Related Nitrogen Compounds

11.1 Nomenclature of amines

11.2 Properties and preparation amines

11.3 Reactions of amines

Exam IV

Final Exam

Assessments

Course Objectives:

|Student Learning Outcomes |How students will |How each |

|(by chapter) |practice each |outcome |

| |outcome |will be |

| |in this course |assessed |

| | |in this course |

|Bonding and Isomerism (Chapter 1) |repeatable online |quizzes exams |

|Define the octet rule. |quizzes | |

|Recognize polar covalent bonds in a molecule | | |

|Recognize a polar molecule | | |

|Draw molecules with multiple covalent bonds | | |

|Determine the valence of a second row element | | |

|Recognize the presence of simple isomerism in organic molecules. | | |

|Define the two types of ions. | | |

|Use Lewis diagrams to illustrate ion formation. | | |

|Write the chemical formula for a simple ionic compound. | | |

|Write Lewis structures for simple organic compounds | | |

|Write Condensed Stick structures for simple organic compounds | | |

|Determine the formal charge on an element in a compound | | |

|Determine the overall charge of an ion | | |

|Recognize resonance structures | | |

|Determine the relative stability of resonance structures | | |

|Recognize resonance hybrids | | |

|Determine the orbitals used in bonding in a compound | | |

|Determine the hybridization of an atom in a compound | | |

|Recognize the presence of a pi bond in a molecule | | |

|Determine the geometry about a carbon atom | | |

|Classify organic molecules base of their molecular framework | | |

|Recognize a heterocyclic compound | | |

|Recognize a carbocyclic compound | | |

|Determine the chemical formula of a simple covalent | | |

|Recognize functional groups in an organic molecule | | |

|Recognize and identify the presence of common functional groups in organic molecules, | | |

|including but not limed to: alcohols, ketones, aldehydes, amines, amides, ethers nitriles, | | |

|thiols and amides. | | |

|• Predict the general shape of a simple organic molecule. | | |

|• Identify hydrocarbons as alkanes, alkenes, alkynes or aromatic | | |

|Alkanes and Cycloalkanes…(Chapter 2) |repeatable online |quizzes |

|Recognize the composition and properties typical of organic and inorganic compounds. |quizzes |exams |

|Identify and name simple (straight-chain) alkanes given formulas and write formulas for | | |

|straight-chain alkanes given their names. | | |

|Learn how alkane molecules can have branched chains and recognize compounds that are | | |

|isomers. | | |

|Write condensed structural formulas for alkanes given complete structural formulas. | | |

|Draw line-angle formulas given structural formulas. | | |

|Name alkanes by the IUPAC system and write formulas for alkanes given IUPAC names. | | |

|Identify the physical properties of alkanes and describe trends in these properties | | |

|Identify the main chemical properties of alkanes. | | |

|Name cyclic alkanes by the IUPAC system and write formulas for cyclic alkanes given IUPAC | | |

|names | | |

|Make reasonable predictions about the overall shape of cycloalkane molecules, especially | | |

|substituted cyclohexanes. | | |

|Identify substituents in cyclohexane structures being axial or equatorial positions. | | |

|Name halogenated hydrocarbons given formulas and write formulas for these compounds given | | |

|names. | | |

|Name cycloalkanes given their formulas and write formulas for these compounds given their | | |

|names. | | |

|Describe functional groups and explain why they are useful in the study of organic | | |

|chemistry. | | |

|Recogzize an oxidation reation of a hydrocarbon | | |

|Recognize an incomplete oxidations reaction from its equations | | |

|Recognize a complete combustion reaction from its equation. | | |

|Write the equation of a free-radical reaction | | |

|Recognize a free radical | | |

|Alkenes and Alkynes (Chapter 3) |repeatable online |quizzes |

|Recognize an alkene and an alkyne |quizzes |exams |

|Identify dienes and polyenes. | | |

|Recognize and classify polyenes as isolated, cumulative or conjugated | | |

|Name alkenes given formulas and write formulas for alkenes given names. | | |

|Name alkynes given formulas and write formulas for alkenes given names. | | |

|Identify bonding in alkenes and alkynes from pictures or formulae | | |

|Recognize alkenes that can exist as cis-trans isomers. | | |

|Classify isomers as cis or trans. | | |

|Identify the various types of bonds (sigma, pi) in orbital diagrams of alkenes and alkynes.| | |

| | | |

|Identify the hybridization of carbon atoms in alkenes and alkynes | | |

|Identify the physical properties of alkenes and describe trends in these properties. | | |

|Recognize a hydrogen halide | | |

|Write equations for the addition reactions of alkenes with hydrogen, halogens, hydrogen | | |

|chloride, hydrogen bromide, and water. | | |

|Use the Markovnikov rule to predict which isomer will be formed in addition reactions of | | |

|alkenes with hydrogen chloride, hydrogen bromide, and water | | |

|Predict the likely product(s) of reaction of alkenes with strong oxidizing agents | | |

|Predict the likely product(s) of reaction of conjugated dienes with halogens and | | |

|hydrohalogens | | |

|Recognize energy diagrams | | |

|Identify all aspects of an energy diagram. E.g activation energy, enthalpy transition | | |

|staqte and reaction intermediate | | |

|Identify a multi-step reaction from its energy diagram. | | |

|Differentiate between the thermodynamic and the kinetics of a reaction | | |

|Identify a carbocation | | |

|Describe the stability of a carbocation from its formula | | |

|Identify an anti-Markovnikov reaction | | |

|Recognize and be able to predict the products of a hydroboration/oxidation reaction | | |

|Recognize a polymerization reaction | | |

|Identify a cleavage reactions | | |

|Recognize the reagents and products of an ozonolysis reaction | | |

|Use the Markovnikov rule to predict which isomer will be formed in addition reactions of | | |

|alkynes with hydrogen chloride, hydrogen bromide | | |

|Predict the likely product(s) of reaction of alkenes | | |

|Describe the general physical and chemical properties of alkynes. | | |

|Name alkynes given formulas and write formulas for alkynes given names | | |

|Aromatic Compounds (Chapter 4) |repeatable online |quizzes |

|Describe the bonding in benzene and the way typical reactions of benzene differ from those |quizzes |exams |

|of the alkenes | | |

|Recognize aromatic compounds from structural formulas. | | |

|Name aromatic compounds given formulas. | | |

|Recognize an electrophilic aromatic substitution reactions | | |

|Predict the products of nitration, halogenation, sulfonation, and Friedel-Crafts reactions | | |

|of aromatic compounds | | |

|Identify ortho/para and meta directing groups base on their chemical formulae | | |

|Identify other aromatic compounds base of their structural formulae | | |

|Recognize a multistep synthesis, and be Able to write chemical equations for the individual| | |

|reactions. | | |

|Predict the products of catalytic hydrogenation of aromatic compounds | | |

|Predict the products of oxidation of side chains of aromatic compounds | | |

|Write formulas for aromatic compounds given their names. | | |

| | | |

| | | |

|Stereochemistry (Chapter 5) |repeatable online |quizzes |

|Identify the existence of stereoisomers given a structural formula |quizzes |exams |

|Recognize the existence of stereocenters given a structural formula | | |

|Determine the name of a stereocenters given a structural formula, including all | | |

|stereochemical descriptors. | | |

|Identify the difference between constitutional isomers and stereoisomers. | | |

|Name the different type of stereoisomers and able to identify the type of isomerism | | |

|exhibited by a particular pair of structures. | | |

|Describe the difference in properties observed for pairs of geometric isomers. | | |

|Draw the structure of a chiral compound using wedge-dash symbolism. | | |

|Draw the structure of a chiral compound using Fischer projection formulas. | | |

|Describe how chemical reactions are different for the two components of a pair of | | |

|enantiomers. | | |

|Describe how the physical properties enantiomeric pairs are the same for most properties | | |

|but are different with regard to interaction with plane polarized light. | | |

|Draw the structures of diastereomers using wedge-dash symbolism. | | |

|Draw the structures of diastereomers using Fischer projection formulas. | | |

|Describe the differences in chemical and physical properties when comparing a | | |

|diastereomeric pair. | | |

|Recognize when a compound exhibits meso forms. | | |

|Organic Halogen Compounds; Substitution and Elimination Reactions (Chapter 6) | | |

|Identify the general structure for an alkyl halide. | | |

|Identify a nucleophile or an electrophile from a chemical formula | | |

|Recognize a nucleophilic substitution reaction | | |

|Recognize a SN1 reaction mechanism, from a chemical equation | | |

|Recognize a SN2 reaction mechanism, from a chemical equation | | |

|Determine the mechanism (SN1 or SN2) Given the equation for a nucleophilic substitution | | |

|reaction | | |

|Recognize an elimination reaction from a chemical equation | | |

|Recognize a E2 reaction mechanism, from a chemical equation | | |

|Recognize a E1 reaction mechanism, from a chemical equation | | |

|Identify a dehydrohalogenation reaction from a chemical equation | | |

|Determine whether the mechanism of a reaction is E1, E2, SN1 or SN2 | | |

|Recognize a SN1 reaction mechanism, from a chemical equation | | |

|Identify a polyhalogenated compound, and deterimine its usages | | |

|Alcohols, Phenols and Thiols (Chapter 7) |repeatable online |quizzes |

|Identify the general structure for an alcohol a phenol and a thiol. |quizzes |exams |

|Identify the structural feature that classifies alcohols as primary, secondary, tertiary | | |

|Name alcohols, phenols and thiols with both common names and IUPAC names. | | |

|Explain why the boiling points of alcohols are higher than those of ethers and alkanes of | | |

|similar molar masses. | | |

|Explain why alcohols of four or fewer carbon atoms are soluble in water while comparable | | |

|alkanes are not soluble. | | |

|Describe how to prepare alcohols from alkenes. | | |

|Predict the product of dehydration of an alcohol. | | |

|Give examples of reactions of alcohols to form ethers. | | |

|Identify a primary, secondary or tertiary alcohol from its chemical formula | | |

|Recognize an alcohol behaving as a base or an acid in a chemical equation | | |

|Identify the conjugate base and the conjugate acid of an alcohol or a phenol or a thiol, | | |

|given a chemical formula. | | |

|Determine the relative acid strength of alcohols and phenols given their chemical formulae.| | |

| | | |

|Recognize a dehydration reaction | | |

|Identify the factors that will result in a dehydration reaction | | |

|Identify the products of a dehydration reaction, given the formulae of the starting | | |

|materials starting materials. | | |

|Identify the products of the reaction of hydrogen halides or thionyl chloride with alcohols| | |

|given the formulae of the starting materials. | | |

|Describe the result of the oxidation of a primary alcohol. | | |

|Describe the result of the oxidation of a secondary alcohol. | | |

|Identify the products of Jones’ reagent or PCC with primary or secondary alcohols | | |

|Predict the products of nitration, halogenation, sulfonation, and Friedel-Crafts reactions | | |

|of phenols | | |

|Describe the structure and uses of some common polyhydric alcohols. | | |

|Explain why phenols are significantly stronger acids than alcohols. | | |

|Describe the process for interconverting disulfides and thiols. | | |

|Ethers and Epoxides (Chapter 8) | | |

|Identify and name simple ethers, aromatic ethers and cyclic ethers. | | |

|Describe the structure differences between an alcohol and an ether that affects physical | | |

|characteristics and reactivity of each. | | |

|Describe the structure and uses of some ethers | | |

|Predict the starting materials needed to synthesize a particular ether using the Williamson| | |

|reaction. | | |

|Recognize an organolithium reagent | | |

|Describe the properties, preparation and uses of a an organolithium reagent | | |

|Identify the products of the reaction of an organolithium reagent with water (D2O) | | |

|Recognize a Grignard reagent | | |

|Describe the properties, preparation and uses of a Grignard Reagent | | |

|Identify the products of the reaction of a Grignard reagent with water (D2O) | | |

|Predict the starting materials needed to synthesize a particular ether using the Williamson| | |

|reaction. | | |

|Identify the products of an alkyl halide and an alkoxide base (RO-) | | |

|Recognize the limitations of the William synthesis for the preparation of ethers | | |

|Predict the products of the cleavage reaction of an ether, given the structure of the ether| | |

|and BBr3 or HI) | | |

|Identify and name simple epoxides. | | |

|Describe the reactivity of an epoxide and an acyclic ether. | | |

|Predict the products of the reaction of an epoxide with an acid, a base, a Grignard reagent| | |

|or an organolithium compound. | | |

|Describe the reaction for the preparation of a given epoxide from an alkene and MCPBA | | |

|Recognize a cyclic ether, and differentiate its reactivity from that of an epoxide. | | |

|Aldehydes and Ketones (chapter 9) |repeatable online |quizzes |

|Identify the general structure for an aldehyde and a ketone. |quizzes |exams |

|Use common names to name aldehydes and ketones | | |

|Use the IUPAC system to name aldehydes and ketones. | | |

|Recognize the different types of oxidation reactions for aldehydes and ketones. | | |

|Describe the reduction reactions of aldehydes and ketones using sodium borohydride. | | |

|Identify aldehydes and ketones that can exhibit tautomerism, and be able to identify the | | |

|tautomers | | |

|Predict the products of aldehydes and ketones with hydrogen cyanide. | | |

|Identify the products of alcohol oxidations with jones’ reagent and PCC | | |

|Describe the electronic nature of the carbonyl group, and contrast it with that of a C=C | | |

|bond | | |

|Compare the boiling points of aldehydes and ketones to those of alcohols and hydrocarbons | | |

|of similar molar mass | | |

|Describe a general nuclephillic addition reaction | | |

|Recognize an acetal, a hemiacetal and a gem diol from their formulae | | |

|Describe, and predict the products of the addition of oxygen nucleophiles (alcohols and | | |

|water) to aldehydes and ketones | | |

|Recognize an imine, an oxime, and hydrazine from their formulae | | |

|Describe, and predict the products of the addition of nitrogen nucleophiles (ammonia and | | |

|amines) to aldehydes and ketones | | |

|Describe, and predict the products of the addition of nitrogen nucleophiles (primary | | |

|amines, hydroxyl amine, and hydrazine) to aldehydes and ketones | | |

|Recognize a cyanohydrin from its formula | | |

|Describe, and predict the products of the addition of HCN, acetylide anion and Grignard | | |

|reagents to aldehydes and ketones | | |

|Recognize the different types of oxidation reactions for aldehydes and ketones. | | |

|Describe the catalytic hydrogenation reactions of aldehydes and ketones. | | |

|Describe the reduction reactions of aldehydes and ketones using sodium borohydride and | | |

|lithium Aluminum hydride. | | |

|Recognize an a-hydrogen in an aldehyde or a ketone | | |

|Predict the equilibrium products resulting from the addition of a base to an aldehyde or a | | |

|ketone. | | |

|Predict the products of the addition of D2O to the conjugate base of an aldehyde or a | | |

|ketone. | | |

|Predict the product(s) of a simple aldol condensation reaction. | | |

|Carboxylic Acids (Chapter 10) |repeatable online |quizzes |

|Identify the general structure for a carboxylic acid, an ester, an anhydride, amide, |quizzes |exams |

|nitrile and an acyl halide. | | |

|Identify the functional group for a carboxylic acid, an | | |

|ester, an anhydride, amide, nitrile and an acyl halide. | | |

|Name carboxylic acids, esters, anhydrides, amides and acyl halides with common names. | | |

|Name carboxylic acids, esters, anhydrides, amides and acyl halides according to IUPAC | | |

|nomenclature. | | |

|Describe the preparation of carboxylic acids. | | |

|Compare the boiling points of carboxylic acids with alcohols of similar molar mass. | | |

|Compare the solubilities of carboxylic acids in water with the solubilities of comparable | | |

|alkanes and alcohols in water. | | |

|Name the typical reactions that take place with carboxylic acids. | | |

|Describe how carboxylic acids react with basic compounds. | | |

|Compare the boiling points of esters with alcohols of similar molar mass | | |

|Compare the solubilities of esters in water with the solubilities of comparable alkanes and| | |

|alcohols in water. | | |

|Identify and describe the substances from which most esters are prepared. | | |

|Describe the typical reactions that take place with esters. | | |

|Identify the products of an acidic hydrolysis of an ester, and amide or a nitrile in base | | |

|or acid. | | |

|Identify the products of a Grignard reagent and carbon dioxide | | |

|Identify the products of an acid catalyzed esterification | | |

|Identify the products of an ammonolysis reaction of an ester. | | |

|Identify the products of a reduction of an ester with lithium aluminum hydride | | |

|Identify the products of a Grignard reagent and an ester | | |

|Identify the products of the reaction of a carboxylic acid and PCl5 or SOCl2 | | |

|Identify the products of the reaction of an acyl chloride with water, ammonia or an alcohol| | |

| | | |

|Identify the products of acetic anhydride with water, an alcohol or ammonia | | |

|Identify the conjugate bases of esters and products of a Claisen Condensation. | | |

|Amines and Related Nitrogen Compounds (Chapter 11) |repeatable online |quizzes |

|Identify the general structure for an amine. |quizzes |exams |

|Identify the functional group for amines. | | |

|Determine the structural feature that classifies amines as primary, secondary, or tertiary | | |

|Use nomenclature systems to name amines. | | |

|Explain why the boiling point of primary and secondary amines are higher than those of | | |

|alkanes or ethers of similar molar mass but are lower than those of alcohols. | | |

|Describe methods of preparation of amines, including hydrogenation, and other methods of | | |

|reduction | | |

|Describe trends in basicity of amines | | |

|Compare the basicity of amines | | |

|Describe common reactions of amines, including acyl and alkyl substitution, reactions of | | |

|and formation of diazonium salts. | | |

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|Student Learning Outcomes |

|(by module) |

|Module 1 (Chapters 1- ?) |

|Please see Learning outcomes for chapter 1-5 above) |

|Module 2 (Chapters ?- ?) |

|Please see Learning outcomes for chapter above) |

|Module 3 (Chapters ?- ?) |

|Please see Learning outcomes for chapter above) |

|Module 4 (Chapters ?- ?) |

|Please see Learning outcomes for chapter 1-5 above) |

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