Chem. 130 Organic Chemistry
Spring 2016
Schedule number: 20645
Professor Jeffrey Gustafson
JGustafson@mail.sdsu.edu
COURSE INFORMATION
Class Days: MWF
Class Times: 11:00-11:50
Class Location: SHW-011
Office Hours: TBD (according to doodle poll on blackboard)
Office Hours Location: CSL 208
Course Overview
Chem 130 covers the fundamental organic chemistry needed for fields related to health and the environment. Importantly this
class will prepare students for Chem 160 (biochemistry), and thus we will spend time on applications of organic chemistry to
biochem (after all biochem is just applied organic chemistry). Organic chemistry differs from general chemistry in that it focuses
on only a few elements (C, H, N, O, F, Cl, Br, I). The 3-dimensional shape of molecules is particularly important and thus a
molecular model kit (sold at book store) is HIGHLY recommended (and will be allowed on exams). We will also discuss
fundamental organic transformations and how they care applied to everyday life.
Enrollment Information
Prerequisites: The prerequisite for Chem 130 is Chem 100. If you have not taken Chem 100 or Chem 200, then you should not
be taking this course. (Note: Other college chemistry courses may qualify as a prerequisite. I will consider these and you should
see me after the first day of class.)
Course Materials
Required Text: Essential Organic Chemistry, 3rd Edition, Paula Bruice (ISBN-13: 978-0321593771-1
Optional Model Kit: Prentice Hall Molecular Modeling Kit for Organic Chemistry (or comparable)
Electronic Homework: The best way to learn organic chemistry is through doing it. Thus 33% of the classes’ grade (360 points,
30 points per chapter) will be from homework. Unfortunately hand graded homework is not feasible so we have to turn to
online homework. We will be using the online homework that comes with the textbook called mastering chemistry. If you go to
blackboard and look on the tool panel you will see a link to ‘mastering chemistry’ that will take you to the homework site. Each
chapter will have pre- and post-chapter assignments. The Pre-chapter assignments are due the day before we start the chapter.
The post-lecture assignments are due a week after we finish the chapter.
Lecture Notes: My personal lecture notes will be put up on Blackboard. These notes cover the major topic I will go over, but are
not a replacement for coming to class and reading the book!! Worked problems and examples done on the board generally
will not be posted. You will miss this material if you don’t attend.
Course Structure and Conduct
This course will be taught in a traditional lecture ‘chalk talk’ format. It is imperative you start the post-chapter homework as
we cover the chapter in lecture. It is also important that you read the book and do the pre-lecture homework before lecture so
that you are somewhat familiar with the material as I present it. As there is a large amount of material to be covered, I ask that
questions be saved for before class, during my office hours, or after my lecture. The best advice for this class is to be proactive.
Start the homework early, come to my office hours if you feel you are falling behind, and read ahead in the book and notes.
Course Assessment and Grading
Exams: There will be three exams during lecture (150 points each) and one final (250 points). Dates: Exam 1 (chap 1-3): Feb
8th. Exam 2 (chap 4-6): March 7. Exam 3 (chapter 7-9): April 11th. Chapters 11-13 will be represented on the final exam. (note
we will not cover chapter 10 in this class).
Final Exam: Monday May 9, 1030-1230 in TBD
There will be three 1 hour midterm exams during the semester, each worth 150 points. There will be roughly 35 multiple
choice questions. The 2 hour final exam is cumulative and is worth 250 points. If beneficial your final exam score can replace
your lowest exam score. Because of this there will be no make-up exams. If you miss an exam, for *any reason*, your final
exam score will automatically replace it. The final exam is not optional and cannot be dropped. There will be no quizzes. The
online homework is worth 360 points. Your final grade will be based on a maximum of 1060 points, distributed as follows: 3
exams (150 points each), 1 Final Exam (250 points), Online Homework (360 points).
Letter Grade Assignment: Depending on class performance the Exams may be curved, but never downward. If necessary the
class average of each exam will be curved upward to a 72 % (the lowest B-).
90%
A
66%
C
86%
A–
62%
C–
82%
B+
58%
D+
78%
B
54%
D
72%
B–
50%
D–
70%
C+
<50%
F
Student Learning Outcomes (broken down by chapter…basically the type of questions that will be asked on exams):
*****Pre chapter homework is due the day we start the chapter Post Chapter homework is due 7 days after we finish the
chapter. Please see mastering chemistry homework schedule linked to blackboard******
Chapter 1 (1/20-1/25)
Explain the terms atomic number, mass number, atomic weight, molecular weight, and isotope.
Describe the relative polarity of bonds, and determine the direction of the dipoles.
Represent compounds using Lewis structures, showing lone pairs and formal charges.
Represent organic compounds using Kekule' structures and condensed structures.
Describe how carbon forms a double bond.
Predict bond angles from the number of lone pairs.
Demonstrate the ability to think critically and employ critical thinking skills.
Chapter 2: (1/27-1/29)
Predict relative acidities and basicities.
Describe the species in a proton-transfer reaction and describe conjugate acids and bases.
Use pKa values of the reactants to determine the products of an acid-base reaction.
Use pKa values to determine the position of equilibrium of an acid-base reaction.
Write equations for acid-base reactions using curved arrows to show where the electrons start from and where they end up.
Predict relative acidities and basicities.
Predict how electronegativity, size, and hybridization affects acidity.
Describe how substituents affect the strength of an acid.
Chapter 3: (2/1-2/5)
Name alkanes using systematic (IUPAC) nomenclature.
Distinguish primary, secondary, and tertiary carbons and hydrogens.
Draw all possible constitutional isomers for a given molecular formula.
raw condensed and skeletal structures of alkanes, alkyl halides, ethers, alcohols, and amines from their systematic and/or
common name.
Predict relative boiling points of compounds based on their structure, polarity, and ability to form hydrogen bonds.
Describe how angle strain is related to ring size.
Identify and draw stereoisomers of disubstituted cyclohexane and predict their relative stabilities.
Describe how angle strain is related to ring size.
Identify and draw stereoisomers of disubstituted cyclohexane and predict their relative stabilities.
Chapter 4:
(2/10-2/17)
Draw constitutional isomers
Identify asymmetric centers.
Identify compounds that can exist as enantiomers.
Identify constitutional isomers, stereoisomers, geometric isomers, enantiomers, diastereomers, and meso compounds.
Draw stereoisomers of cyclic compounds and recognize whether a pair of stereoisomers are identical, enantiomers, or
diastereomers
Determine the configuration of enantiomers.
Chapter 5: (2/19-2/24)
Name an alkene given its structure, and draw the condensed and/or skeletal structure of an alkene given its name.
Predict the relative stabilities of alkenes based on their structures and/or heats of hydrogenation.
Show how curved arrows can be used to describe the bond-breaking and bond-making steps that occur as reactants are
converted into products, and how they can be used to predict the product of a reaction.
Chapter 6: (2/26-3/4)
Identify the orbitals used in formation of a triple bond.
Name an alkyne given its structure, and draw the structure of an alkyne given its name.
Identify and draw keto-enol tautomers.
Predict the products obtained from the addition of hydrogen to an alkyne.
Describe how alkyl halides, alcohols, and alkanes can be synthesized from alkenes.
Predict the products formed from the addition of a hydrogen halide to an alkene.
Predict the products formed from the acid-catalyzed addition of water to an alkene.
Predict the products of the acid-catalyzed addition of water to an alkyne.
Predict the products obtained from the addition of hydrogen to an alkyne.
Predict the stereoisomers obtained from electrophilic additions reactions of alkenes.
Chapter 7 (3/9-3/16)
Draw resonance contributors and resonance hybrids.
Rank resonance contributors according to their predicted stabilities.
Propose mechanisms for reactions for compounds with double bonds.
Predict the products of Diels-Alder reactions.
Predict relative reactivities of dienophiles in Diels-Alder reactions.
Chapter 8 (3/18-3/23)
Predict the products of nucleophilic substitution reactions, including their stereochemistry.
Predict the major products of elimination reactions, including their stereochemistry.
Predict how the alkyl group affects the rate of a nucleophilic substitution reaction.
Predict how changing the concentration of the reactants affects the rate of substitution and elimination reactions.
Predict how the alkyl group affects the rate of a nucleophilic substitution reaction.
Predict how the leaving group affects the rate of a nucleophilic substitution reaction.
Predict how the alkyl group and/or the leaving group affects the rate of an elimination reaction of an alkyl halide.
Predict how changing the polarity of a solvent will affect the rate and/or the equilibrium constant of a reaction.
Describe how compounds can be synthesized using nucleophilic substitution reactions.
Chapter 9 (3/25-4/8 ***spring break is 3/28-4/1***)
Name an alcohol given its structure, and draw the structure of an alcohol given its name.
Decribe how alcohols can be converted to alkyl halides.
Predict the major products of the dehydration of alcohols and describe the relative rates at which alcohols undergo
dehydration.
Predict the products of the reactions of alcohols with oxidizing reagents.
Propose mechanisms for the dehydration reactions of alcohols.
Predict the major products of the dehydration of alcohols and describe the relative rates at which alcohols undergo
dehydration.
Predict the products obtained from ether cleavage (including the mechanisms).
Predict the products obtained from the reaction of epoxides with nucleophiles (including the mechanisms) and why the product
of the reaction depends on whether the reaction is carried out under acidic or neutral/basic conditions.
Describe how alcohols can be converted to alkyl halides.
Show how to convert an alcohol to a related compound with a different functional group.
Chapter 11: (4/13-4/18)
Name carboxylic acids and carboxylic acid derivatives and, given their names, draw their structures.
Describe how an acid catalyzes the hydrolysis of an ester.
Predict the products of the reactions of carboxylic acids and carboxylic acid derivatives with nucleophiles.
Predict the products of the reactions of carboxylic acids and carboxylic acid derivatives with nucleophiles.
Predict the products of the reactions of carboxylic acids and carboxylic acid derivatives with nucleophiles.
Describe how carboxylic acid derivatives can be synthesized.
Describe how acyl chlorides can be used to prepare carboxylic acid derivatives.
Predict the products of the reactions of carboxylic acids and carboxylic acid derivatives with nucleophiles.
Describe the conditions needed to form an amide.
Describe the mechanism for acid-catalyzed hydrolysis of an amide
Predict the products of the reactions of carboxylic acids and carboxylic acid derivatives with nucleophiles.
Describe the mechanism for the reaction of carboxylic acids and carboxylic acid derivatives.
Chapter 12: (4/20-4/25)
Name aldehydes and ketones and, given their names, draw their structures.
Describe how hemiacetals and acetals are formed.
Describe the difference between conjugate and direct addition and the types of nucleophiles that undergo each reaction.
Predict the products of the reactions of aldehydes, ketones, and carboxylic acid derivatives with nucleophiles.
Propose methods that can be used to synthesize alcohols.
Show how amides can be used to synthesize a variety of compounds.
Identify the products obtained from the reaction of carbonyl compouns with hydride ion.
Chapter 13: (4/27-5/2)
Explain why the a-hydrogen of aldehydes, ketones, and esters are acidic and predict their relative acidities.
Draw keto-enol tautomers and the mechanisms for intercoversion of the tautomers.
Predict the products of aldol additions and retro-aldol additions.
Predict the products of Claisen condensations.
Predict the carboxylic acids that will undergo decarboxylation when heated.
Draw keto-enol tautomers and the mechanisms for intercoversion of the tautomers.
Demonstrate how a substitutent can be placed on the a-carbon of a ketone.
Predict the products of crossed aldol additions.
Students with Disabilities
If you are a student with a disability and believe you will need accommodations for this class, it is your responsibility to contact
Student Disability Services at (619) 594-6473. To avoid any delay in the receipt of your accommodations, you should contact
Student Disability Services as soon as possible. Please note that accommodations are not retroactive, and that accommodations
based upon disability cannot be provided until you have presented your instructor with an accommodation letter from Student
Disability Services. Your cooperation is appreciated.
Academic Honesty
The University adheres to a strict policy regarding cheating and plagiarism. These activities will not be tolerated in this class.
Become familiar with the policy (http://www.sa.sdsu.edu/srr/conduct1.html). Any cheating or plagiarism will result in failing
this class and a disciplinary review by Student Affairs.
Examples of Plagiarism include but are not limited to:

Using sources verbatim or paraphrasing without giving proper attribution (this can include phrases, sentences,
paragraphs and/or pages of work)

Copying and pasting work from an online or offline source directly and calling it your own

Using information you find from an online or offline source without giving the author credit

Replacing words or phrases from another source and inserting your own words or phrases

Submitting a piece of work you did for one class to another class
If you have questions on what is plagiarism, please consult the policy (http://www.sa.sdsu.edu/srr/conduct1.html) and this
helpful guide from the Library:( http://infodome.sdsu.edu/infolit/exploratorium/Standard_5/plagiarism.pdf)
Extra help and tips for Success
Help is available in a variety of forms.
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Work with your classmates on difficult material.
Talk to your laboratory TA.
Get a tutor. The Chemistry office (GMCS 209) or I can also help you to find one.
There will be a review session the Thursday before each exam at 5:00 PM.
10 Musts to get a good grade:

Attend all lectures and labs.
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Read material in book and notes before lecture, prior knowledge will help you become engaged in lecture and better
comprehend material.
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Write questions down, and attend office hours.
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Do assigned homework (worth more than an exam!).
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Discuss concepts with classmates, or study partner.
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Don’t fall behind!
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Try to see the big picture. Organic chemistry builds upon itself. Many of the topics within a chapter are just a slight
variation of something you learned.
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Be curious. Always ask why? Curiosity makes a scientist tick.
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Focus on understanding concepts, not memorization.
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Actively read tests and notes… every few minutes you should try a problem.
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With Studying it is quality not quantity. Focus on comprehension not memorization.