Chemistry 261: Organic Chemistry I, Fall 2015
001: TR8:00 - 9:15 Chapman 211
002: MWF 11:15-12:05 Murray G202
Instructor: Dr. Jennifer Krumper Course webpage: sakai.unc.edu
Text:Organic Chemistry (Bruice, 7th ed.)Prerequisite: a grade of C- or better in 102
Other Materials:i>Clicker brand clicker (required; use any clicker made by this company), subscription to ALEKS (required; available online), subscription to MasteringChemistry (required; bundled with your textbook at the bookstore), HGS model kit (required), student solutions manual (optional).
Contact Information. To promote personal connection, reach me in person rather than by email. Use email () only in emergency situations.
Bring science or course content questions to Q&A sessions. This way, all students have equal access to help with tough topics in the class.
Q&A sessions: Locations: ★ = Murray G202; = Murray G307; = KenanC143; $$= Chapman 211
Day / Early / Late Afternoon / EveningM / 2:30-3:15 (Dr. K.; ★) / 6:00-7:00 (261 mentors; )
Tu / 12:00-12:45 (Dr. K.; ) / 3:30-4:30 (Dr. C.; ★) / 7:00-8:00 (261 mentors; $$)
W / 8:30-9:30 (261 mentors; ) / 2:30-3:15 (Dr. J.; ★)
Th / 2:00-2:45 (Dr. K.; ★) / 6:00-7:00 (261 mentors; $$)
Office hours (non-science questions): Kenan C147F
W: 1:30-2:15F: 2:45-3:30 or: catch me after class or a Q&A session
Office hours are set aside for questions about logistic matters, general strategies for success, or just to say hello. I would love to meet you, so make it a point to drop by at least once during the semester.
If you wish to discuss an examin office hours, bring: 1) the exam you wish to discuss, 2) your notes + practice problems, and 3) a completed post-exam reflection survey (available on sakai).
Course Description
Chemistry 261 is the first half of a two semester, cumulative overview of organic chemistry. We will cover the fundamental tools of organic chemistry and apply these to the reactions of alkanes, alkenes, alkynes, alkyl halides, ethers, and alcohols.
You may find this course unusual for a science class, and surprisingly similar to acquiring a second language. You will only be asked to perform simple mathematical operations, but you will learn many reagents (nouns) and to develop a feel for the mechanisms (verbs) by which these reagents act. Later, you will approach multi-step chemical synthesis, which is analogous to sentence construction.
Becoming fluent in the language of organic chemistry requires deep learning and long-term retention of what you’ve learned. This can be achieved only by working a wide variety of practice problems and by engaging deeply with the material every day.
The Chemistry 261 Community
Our class emphasizes teamwork and good sportsmanship. Grading is on a flat scale, not a curve. In Chemistry 261, therefore, ultra-competitive behavior is not only unattractive,it is also unnecessary.
Academic Honesty
Cheating is NOT a part of the Chemistry 261 culture, nor does it benefit the cheater. Academic dishonesty carries heavy consequences:
Some student work (e.g. exams, MasteringChemistry) must be completed individually and without external aids. Other work (e.g. group questions in class) may be completed with help from peers and/or selected external aids. If you are unsure whether a task is intended to be individual or group work or whether you may use outside aids, ASK!
All course materials including notes and assignments are covered by University Copyright Policy:
Chemistry 261 is an Engaged-Learning Class
How well you learn depends largely on your choices: do you engage with the material every day, or do you cram for exams? Do you think deeply about what you’re learning, or do you skim the surface? The course structure ofChem 261 is designed to reward activities that support learning with class points. These are called Daily Work Points, and they comprise 15% of your grade.
To earn Daily Work Points, you will prepare for each week of class with a pre-class assignment: video lectures and/or selected textbook reading to do, followed by a graded ALEKS or MasteringChemistry problem-solving activity. We will then check your understanding in class and delve into more challenging topics with clickerquizzesand group work. Chemistry 261 mentors and I will rove during these activities help you build the skills you need in the right way. After class, you will reinforce your skills by doingtextbook practice problems and graded online self-tests(in MasteringChemistry) to ensure you have mastered the skills of organic chemistry. Each part of this class structure has been shown to improve success in chemistry.
You may not earn a score higher than 100% on Daily Work, but many more Daily Work points will be offered than are necessary to earn a 100% (see Daily Work grading chart). This will allow you to make up points lost by the occasional missed class, dead clicker battery, or missed MasteringChemistrydeadline.
Daily Work and Attendance
Your overall Daily Work score (15% of your grade) is roughly 50% based on in-class work. Excellent attendance is required.
ALEKS: Course Code = JW9TN-TJF6L
We will use an online learning system called ALEKS for the first few weeks of the term. ALEKS is quite different from other online homework systems: it assesses your skills and assigns specific tasks catered to you. No two students will have exactly the same set of learning tasks in ALEKS. Work individually in ALEKS. The program is designed such that collaboration of any kind will create a significant amount of extra work for you. More information is available under “261 Startup” on sakai.
Pre-Class Assignments
Video lecturesand/or reading will be assigned before each week of classes. ALEKS Objectives and/or pre-class questions in MasteringChemistry(Course = KRUMPER261FA2015)will due each Sunday night to hold you accountable for these Pre-Class Assignments. These assignments aregraded and required: their content will be tested on exams.
Pre-class assignments in MasteringChemistry and/or ALEKS will be due at 11:59pm on Sundays.
Clicker Activities
We will do a variety of problem solving activities in class using clickers. Some activities will test your mastery of the Pre-Class Assignment. For these clicker quizzes, you will be instructed to work individually, and your score will be based on your performance.You may use notes you have taken on the Pre-Class Assignment on the clicker quiz, but other materials (e.g. your book) are excluded.
Throughout class period, we will learn new concepts and skills in lecture, then apply these to real organic chemistry problems. You will work together with a team to master these tasks. You will earn points for simply participating in these activities.
No makeups will be given for in-class clicker points. (See notes on Daily Work and Attendance above.)
Practice Problems
A list of recommended practice problems from your text for each exam’s content will be posted under “Daily Work and HWK” on sakai. These practice problems are the key to your success in Organic Chemistry. Years of experience have shown me that successful students in the course doall of the recommended textbook problemsand they open their textbooks to solve problems every day.
Self Tests in MasteringChemistry: Course = KRUMPER261FA2015
Self Tests will be assigned in MasteringChemistryon a weekly basis. Self Test problems are much like end-of-chapter problems from the textbook, and they are intended to augment, rather than replace textbook practice. Consider your performance on Self Tests as a measure of whether you have done enough practice problems. You will have 90 minutes to complete each week’s Self Test.
No late work will be accepted in MasteringChemistry for any reason. The MasteringChemistry clock will be used to determine the submission date/time. This clock may differ from yours, so submit your work well in advance. You may use your book or other resources,but all MasteringChemistry assignments are to be worked by you alone. No collaboration is allowed before the due date, but discussion of MasteringChemistrycontent is encouraged after you’ve turned it in.
Self Tests in MasteringChemistry will be due at 8:00 am on Wednesdays.
Quizzes, Exams, and Final
See schedule for dates of midterms and the final. Unless you have a valid medical, emergency, or university sanctioned excuse, a missed exam will be scored as a zero. Excused absences must be accompanied bydocumentationfor alternative arrangements to be made. If you know will need to miss an exam in advance (e.g. for a medical procedure or University field trip), you may arrange to take the exam early. Arrangements for early exams must be made at least two weeksin advance. Email Dr.K. if you become ill on the day of the exam or have a last minute difficulty taking the exam.
Q&A Sessions
Attendance at Q&A sessions (see schedule on first page) will be encouraged with Daily Work points, and you can collect these points by completing a weekly poll in sakai. If you are totally unable to attend any of the Q&A sessions for a week, you may attest to this fact (on your honor) and be awarded credit in absentia.
Weekly Q&A attendance polls will be due on sakaiat 11:59pm on Sundays.
Grading
Your Daily Work % score will be calculated as a % of 200Daily Work points.More than 280 points of Daily Work will be available, but your score may not exceed 100%.
Item / Points ea. / Number / Min. total pts.
ALEKS / 36 / 1 / 36
Clicker Activities (every class period) / MWF: 4
TuR: 6 / ~ 35
~23 / ~ 140
MasteringChemistry Pre-Class assignments / 3 / ~12 / ~36
MasteringChemistry Self-Tests / 3 / ~12 / ~36
Review Session Attendance (credit for 1 per week) / 3 / ~12 / ~36
Minimum Daily Work Points Available / >280
Maximum Daily Work Points Applicable to Final % score / 200
Grade Breakdown
Item / Points Possible / % of Grade
Daily Work (more info below) / Daily Work % score is scaled to 75 points / 15%
Midterms / 300
(3 scores: 100 ptseach) / 60%
(3 scores: 20% each)
Final Exam / 125 / 25%
Total / 500 / 100%
Grade thresholds may be scaled down at the instructor’s discretion, but guaranteed minimum values are listed below. (e.g. a score of 68% is guaranteed a C-)
Percentage score / Course grade / Percentage score / Course grade / Percentage score / Course grade / Percentage score / Course grade
93.0 – 100 / A / 87.0 – 89.9 / B+ / 75.0 – 79.9 / C+ / 60.0-66.9 / D
90.0 – 92.9 / A- / 83.0 – 86.9 / B / 70.0 – 74.9 / C / < 60.0 / F
80.0 – 82.9 / B- / 67.0 – 69.9 / C-
How to Succeed in Organic Chemistry
Be a good class citizen. Smile at your classmates and introduce yourself to them. Ask someone how their day is going. Switch off all electronic devices (phones, computers, etc.) while in class.
Print up the list of recommended textbook practice problems and mark your progress on it. Keep a spiral notebook or binder for your practice problems; it is useful for the purpose of review to have them all collected in one location.
Do some organic chemistry every day. Complete all the Pre-Class Assignments before coming to class. Complete all the recommended practice problems. Stay on top of your ALEKS work and Sapling Homework.
A good study session feels like a hard workout; expect to be tired afterwards. Be well rested when you start studying and study with focus + determination.
How to Succeed in Organic Chemistry, Continued
Use the textbook wisely. While each student learns differently, be wary of over-reliance on the textbook. We will not cover every topic presented in the assigned chapters in Bruice, and we may cover topics with less or more detail than Bruice. As such, it can be a poor use of time to read the textbook carefully. Student time is often better spent working problems and using the text for reference, rather than to learn material. Specific sections that are important for you to read thoroughly will be flagged in your pre-class assignment. If a section is not flagged, however, it is suggested that you learn the content from theassigned video or lecture notes, rather than the text. For non-flagged sections, you are urged to use the text for reference only.
Hand write your notes, both from the videos and in class. You may take notes on a tablet, but organic chemistry requires a great deal of drawing; typing is not practical. Keep notes organized, and take notes in more than one color. Color-coding greatly assistsin tracking the movement of atoms in organic reactions.
Review to the class notes posted on sakai after class. The class is fast-paced and clicker activities are presented rapid fire. Your time is best spent working out solutions to questions rather than transcribing question text. It is wise to take sketchy/partial notes on in-class questions: just enough to flag the question in your notes and work out an answer. All notes and clicker activities presented in class are posted on sakaiimmediately after class. Look these up and fill in the gaps in the notes you took on in-class questions.
Attend Q+A sessions. There are many Q&A sessions offered each week, hosted both by mentors and by Dr.K. Attend these sessions. Bring your questions and/or just bring your desire to learn.
Form a study group.Working with a study group outside of class will help you learn the material deeply. Your in-class working group is a great place to form these connections. Exchange contact information and follow up – call others and ask if they want to study together.
Make and study flash cards. It is extremely helpful to work with a shuffle-able deck of reaction flash cards when we get into reaction chemistry (Chapter 6 and beyond). Flash cards train you to recognize reactions without the context cues provided by seeing them on a page in your notes or the text. The act of making the flash cards is also an excellent way to review the reactions we’ve learned.
Use non-assigned electronic resources. If you purchase a current version of textbook in the bookstore bundle or an eText, you will receive free access to MasteringChemistry. Mastering offers a “study area” with a host of practice multiple-choice problems. Google can provide a wealth of extra practice problems, too.
Venues for extra help with 261:
1)The Learning Center coordinates free tutoring by appointment:
2)The chemistry department recommends tutors for hire:
Tentative Schedule: Chemistry 261, Fall 2015, section 001 TR 8:00 amDate / Day / # / Topics/Skills / Relevant Text Sections/Events
8/18 / Tu / 1 / Chemistry 101 review: electronegativity, structural formulae, Lewis Structures, formal charges, resonance / 1.0 – 1.4, 2.8
8/20 / Th / 2 / resonance, skeletal structures / 8.3 – 8.6, some 3.3
8/25 / Tu / 3 / Chemistry 101 review: atomic and molecular orbitals, hybridization / 1.5 – 1.12
8/27 / Th / 4 / Chemistry 101 review: hybridization & molecular geometry / 1.13 – 1.16, 2.1 –2.6
9/1 / Tu / 5 / Bronsted and Lewis; Alkane Nomenclature; Functional Groups / 2.6 – 2.9, 2.12; 3.1 – 3.6; 5.5; 3.7
9/3 / Th / 6 / Acyclic alkane conformations: C-C bond rotation / 3.8 – 3.10
9/8 / Tu / 7 / Cycloalkane conformations; Thermodynamics of equilibrium / 3.11 – 3.15; pp. 206-207
9/10 / Th / 8 / Chirality, enantiomers / 4.1 – 4.6
9/15 / Tu / 9 / Optical activity, multiple stereoisomers / 4.7 – 4.14
9/17 / Th / 10 / alkene structure, stereochemistry, kinetics, + thermodynamics in the context of electrophilic addition of HX to an alkene / 5.1 – 5.6; 6.1 – 6.3 (Background: 5.7; 5.9 – 5.12 (skip p.215))
9/22 / Tu / 11 / Exam 1 / Chapters 1-4
9/24 / Th / 12 / Hammond Postulate, cation stability, hydration / 6.4 – 6.5
9/29 / Tu / 13 / Hydration and alcohol addition / 6.5 – 6.7
10/1 / Th / 14 / carbocation rearrangements, hydroboration; X2 addition, peroxyacid oxidation / 6.7– 6.10
10/6 / Tu / 15 / ozonolysis, hydrogenation, alkene stability, stereochemistry review, synthesis / 6.11 – 6.15; 6.18
10/8 / Th / 16 / Alkyne reactivity, Alkynes + HX, X2, Alkyne hydration / 7.1, 7.4 – 7.8
10/13 / Tu / 17 / Addition of H2 to alkynes,Alkyne deprotonation, C-C bond formation, synthesis / 7.9 – 7.12
10/15 / Th / Fall break / No class
10/20 / Tu / 18 / Additions to dienes,Review and Synthesis practice / 8.17 – 8.18; 6.14-6.15, 6.18, and 7.12
10/22 / Th / 19 / Exam 2 / Chapters 5-7
10/27 / Tu / 20 / Introduction to SN2; Factors and Trends for SN2, SN1 / 9.1 – 9.4
10/29 / Th / 21 / SN1/2 competition, solvent effects / 9.5 –9.9
11/3 / Tu / 22 / Intro to E2, intro to E1; E2 stereochemistry / 10.1 –10.4; 10.6 – 10.7
11/5 / Th / 23 / More on E1/2; SN1/2 vs. E1/2 and synthesis using these reactions / 10.5 –10.11
11/10 / Tu / 24 / Intro to alcohols / 11.1 – 11.4
11/12 / Th / 25 / Oxidation of alcohols, ethers, epoxides / 11.5 – 11.8
11/17 / Tu / 26 / Epoxides; intro to radicals / 11.7 – 11.8; 13.1 – 13.3
11/19 / Th / 27 / Exam 3 / Chapters 8-11
11/24 / Tu / 28 / Reactivity and selectivity in halogenation, Radical additions to alkenes; Allylic and benzyllic halogenation; / 13.4 – 13.5; 13.7 – 13.9
11/26 / Th / Thanksgiving Break / No class
12/1 / Tu / 29 / synthesis with radicals and REVIEW / 13.10
12/10 / Th / Final Exam section 001: 8:00 am, Chapman 211
Tentative Schedule, Fall 2015, Section 002 MWF 11:15 am
Date / Day / # / Topics/Skills / Relevant Text Sections
8/19 / W / 1 / Chemistry 101 review: electronic structure, electronegativity, structural formulae, covalent bonds, Lewis Structures / 1.0 – 1.4
8/21 / F / 2 / Chemistry 101 review: Lewis Structures, formal charges, resonance, skeletal sturctures / 2.8, 8.3 – 8.6, some of 3.3
8/24 / M / 3 / Chemistry 101 review: atomic and molecular orbitals, hybridization / 1.5 – 1.9
8/26 / W / 4 / Chemistry 101 review: hybridization & molecular geometry / 1.10 – 1.14
8/28 / F / 5 / hybridization practice, Bronsted Acids / 1.15 – 1.16; 2.1 – 2.6
8/31 / M / 6 / Bronsted Acids: structural factors / 2.6 – 2.7
9/2 / W / 7 / Bronsted and Lewis Acids; Functional Groups, Nomenclature / 2.9, 2.12, 5.5, 3.1 – 3.4, 3.6
9/4 / F / 8 / Physical properties, Acyclic alkane conformations: C-C bond rotation / 3.8 – 3.10
9/7 / M / Labor Day / No class
9/9 / W / 9 / Cycloalkane conformations; Thermodynamics of equilibrium / 3.11 – 3.15; pp. 206-207
9/11 / F / 10 / Chirality, enantiomers / 4.1 – 4.6 (skip Fischer projections)
9/14 / M / 11 / R and S naming, Optical activity, and enantiomeric excess / 4.7 – 4.10
9/16 / W / 12 / Multiple stereocenters / 4.11 – 4.14
9/18 / F / 13 / alkene structure, stereochemistry, curved arrows / 5.1 – 5.6
9/21 / M / 14 / Exam 1 / Chapters 1-4
9/23 / W / 15 / kinetics, + thermodynamics in the context of electrophilic addition of HX to an alkene / 6.1 – 6.3 (Background: 5.7; 5.9 – 5.12 (skip p.215))
9/25 / F / 16 / Markovnikov’s Rule, cation stability, Hammond Postulate / 6.4 – 6.7
9/28 / M / 17 / Addition of H2O and ROH / 6.5– 6.6
9/30 / W / 18 / Addition of ROH, carbocation rearrangements, hydroboration / 6.6– 6.8
10/2 / F / 19 / hydroboration, X2 addition, peroxyacid oxidation / 6.8 – 6.10
10/5 / M / 20 / ozonolysis, hydrogenation, alkene stability,stereoselectivity in addition rxns / 6.11 – 6.15
10/7 / W / 21 / Synthesis; Alkyne reactivity, Alkynes + HX, X2 / 6.18; 7.1, 7.4–7.6
10/9 / F / 22 / Alkyne hydration + tautomerization, / 7.7 – 7.8
10/12 / M / University Day / No Class
10/14 / W / 23 / Addition of H2 to alkynes; alkyne deprotonation, C-C bond formation, synthesis / 7.9 – 7.12
10/16 / F / Fall Break / No Class
10/19 / M / 24 / Dienes / 8.17 – 8.18
10/21 / W / 25 / Exam 2 / Chapters 5-7
Tentative Schedule, Fall 2015, Section 002 MWF 11:15 am, Continued
10/23 / F / 26 / SN2 Introduction / 9.1
10/26 / M / 27 / SN2 Factors and Trends; SN1 / 9.2 - 9.4
10/28 / W / 28 / SN1, SN1/2 competition / 9.5 – 9.6
10/30 / F / 29 / solvent effects, Intramolecular substitution reactions and biological examples / 9.7 – 9.9
11/2 / M / 30 / E2 with stereochemistry / 10.1– 10.2, 10.6 – 10.7
11/4 / W / 31 / More on E2 stereochemistry, E1 with stereochemistry / 10.3 –10.7
11/6 / F / 32 / SN1/2 vs. E1/2 and synthesis using these reactions / 10.9 – 10.10
11/9 / M / 33 / Intro to alcohols / 11.1 – 11.2
11/11 / W / 34 / More on alcohols / 11.3 – 11.4
11/13 / F / 35 / Oxidation of alcohols, ethers / 11.5 – 11.6
11/16 / M / 36 / Ethers and Epoxides / 11.6 – 11.7
11/18 / W / 37 / Intro to radical halogenation / 13.1 – 13.3
11/20 / F / 38 / Exam 3 / Chapters 8-11
11/23 / M / 39 / Reactivity and selectivity in halogenation, Radical additions to alkenes / 13.4 – 13.5; 13.7
11/25-11/27 / W / Thanksgiving Break / No class
11/30 / M / 40 / Allylic and benzyllic halogenation; synthesis with radicals / 13.8 – 13.10
12/02 / W / 41 / REVIEW
12/04 / F / 12:00 pm:Final Exam for section 002