Syllabus: SCC 251 – Organic Chemistry – Spring 2022

LAGUARDIA COMMUNITY COLLEGE
CUNY NATURAL SCIENCES DEPARTMENT

Organic Chemistry I SCC 251           

Course Instructor:  Professor J. Gonzalez

Office: M-206        Email: jagonzalez@lagcc.cuny.edu

Course Description:     

This course is part I of a two-semester sequence emphasizing, structure, reactivity, mechanisms and synthesis of alkanes, alkenes, alkynes, alkyl halides, stereochemistry, substitution, and elimination reactions. The laboratory stresses basic organic chemistry techniques.  The prerequisite is: SCC202.

The following is what is required to successfully pass this online course.

  • A computer (desktop/laptop) or mobile device (smartphone, tablet, iPad)
  • Microphone, speakers, headset, or earbuds
  • Stable high-speed internet connection
  • Webcam
  • Microsoft Office (Word, Excel, PowerPoint)
  • LaGCC student email
  • Zoom app

In order to be marked as present all student participants will be required to have their videos on and be on camera during lectures, labs and exams.

Some Advice:      

“ORGO.” You’ve heard horror stories about it, you’ve had nightmares about it and now you’re in the class! Before you switch majors, “Orgo” doesn’t have to be all that terrifying.  The question is why are you taking this course? Many of you will say you need organic chemistry to “get into that school, get that degree or get that job.” In other words, you need it to realize your career objectives.  You and I both know that once you finish your year of organic you will forget all about carbon, nomenclature, reactions, and mechanisms. So, what is really the point?

Organic chemistry teaches you how to solve problems in ways you may not have thought of before.  It teaches you to learn a concept, absorb the concept then manipulate the concept in different ways to solve a problem you have never been exposed to before.

This is a little different than “Gen Chem”, where you have equations, or you can derive a different equation to solve a problem.  Here you need to find the best theory or model to solve the problem at hand—and there may be more than one approach to the answer, more than one synthesis route to get the compound or more than one mechanism to explain the product.

Organic chemistry is challenging; no doubt about it. I will ask you questions not found in any book and not searchable on Google.  You will learn not to be afraid to tackle and solve problems on your own with no “solutions manual”.

My promise to you is that organic chemistry will help you acquire and improve your problem-solving skills and critical thinking skills—skills that are highly valued across all professions and anyone who is truly successful needs to develop these skills to solve problems.

Here is some advice for getting you through the first semester.

  • Don’t memorize.  Success in this course as in life is based on understanding WHY. WHY the reactions happen and how mechanisms occur.  Many of the concepts in this course will become clear after you have had a chance to analyze and review.  This review period is essential; therefore, you need to schedule regular study periods of at least 4 hours per day. As the semester progresses cramming will be impossible. 
  • Take notes and re-write them.  Write, re-write, re-write again then analyze your notes!  Listening to lectures and looking at PowerPoint slides will lull you into thinking that you understand the material but not so; only by writing and again re-writing the notes will you truly understand the ideas and reactions.
  • Form study groups with your colleagues, network!  You will be amazed at how much you can help each other.  And work on solving additional problems within the chapter or other textbooks for more practice. Create your own exam questions. 
  • Make the most of the resources you have available, including other textbooks, online sites, tutoring and OFFICE HOURS!  Do not wait till the day before a major exam to find me—that will be too late!

There is a brilliant organic chemistry professor, Brian Coppola at University of Michigan and he tried to find out what was the “magic” combination of things that students did (tutoring, online resources, re writing notes, study groups, etc.) to get B+ or better in organic.  After 20 years he could find no magic combination—–but what the unpublished study did show was that as long as the student did 6 activities outside the class consistently then their grades were far and above their peers’ grades. I suggest making a list of what strategies you will use to tackle organic chemistry, make sure you use at least 6 techniques!

List of activities pick any 6 or develop your own.

  • Read other textbooks
  • Summarize the material as you read
  • Re-write notes several times
  • Create concept maps
  • Form study groups
  • Do varied homework problems
  • Attend tutoring
  • Take practice exams
  • Find online resources
  • Take quizzes
  • Create outlines
  • Develop flash cards

Finally, stay focused and involved. If you give organic chemistry a chance, we can make it interesting and creative. Good Luck!

Suggested Text:  Organic Chemistry 10th edition, Francis A Carey, Robert M. Giuliano, McGraw Hill 2017.

Lectures

The procedure is the following; 

  1. Before each class you need to read the corresponding sections of the textbook.  As always you are not limited to the textbook
  2. I will send a Zoom link 15 min the lectures. 
  3. We will have our lecture and labs via Zoom conferencing. 
  4. All exams will be on Blackboard
  5. This schedule is subject to change without notice 

Students with Disabilities:

Every attempt will be made to accommodate any student with disabilities.  If you have a documented or undocumented disability, please see me after class as soon as possible to discuss necessary accommodations and/or contact the Office for Students with Disabilities at (718) 482-5279 or go to room M-102

Grading

Keep in mind there is NO extra credit given for this course

Evaluation:

Exams (3) @ 125 pts each                                     375 points

Cumulative Departmental Final                             125 points

Laboratory                                                           400 points

Total                                                                    900 points

Grading Standards:

A minimum of 60% out of 1000 points must be earned to receive a passing grade of D-

Grading Scheme:

A = 93-100                     A- = 90-92.9                           

B+ = 87-89.9                  B = 84-86.9                    B- = 80-83.9

C+ = 77-79.9                  C = 73-76.9                    C- = 70-72.9

D+ = 67-69.9                  D = 63-66.9                    D- = 60-62.9

F = < 60

Academic Integrity Policy:

Students are required to observe the College Policy regarding cheating on examinations and quizzes. A complete statement of the policy is available at the student counseling services.   Academic Dishonesty is prohibited in the City University of New York and is punishable by penalties ranging from a grade of F” on a given test, research paper or assignment, to an “F” in the course, or suspension or expulsion from the College.  Please visit this website to learn more about what is classified as academic dishonesty by CUNY (http://library.laguardia.edu/files/pdf/academicintegritypolicy.pdf)

Attendance Policy:

Attendance at all class sessions, lecture, and laboratory, is essential for proper understanding and mastery of the course material.  A student who is absent from more than one laboratory session seriously jeopardizes his/her grade for the course. The maximum number of unexcused absences is limited to 15% of the number of class hours, about 4 lectures.

Cell Phone Policy:

The use of cell phones, smart phones, or other mobile communication devices is disruptive, and is therefore prohibited during class. Except in emergencies, those using such devices must leave the classroom for the remainder of the class period. The use of cell phones in class is prohibited.

Make-up Policy:

There will be no make-up exams.  A student who has missed a test must have a doctor’s note.

Outline for OER Organic Chemistry I

Sections from Suggested Textbook Carey/Giuliano 10th Edition

Week 1

Review of Lewis Bonding Theory

  • Electrons, orbitals & ionic bonding (sections 1.1, 1.2)
  • Covalent, polar, dipoles electronegativity bonds, Lewis formulas, Octet Rule (sections 1.3, 1.4, 1.6)
    • multiple bonding
    • formal charge (sections 1.5)
  • Shorthand for chemists (section 1.4)
    • line bond formulas
    • dashes and wedges
    • curved arrows
  • Hybridization
    • sp3 hybridization (section 2.6)
    • sp2 hybridization (section 2.8)
    • sp hybridization (section 2.9)
  • Formal Charge
    • Formal charge (1.5, 1.6)
    • Dipole moments (1.10)
  • Resonance
    • Drawing resonance structures (1.7, 1.11)
    • Energy of resonance structures
    • Structure and reactivity from resonance
  • Alkanes & Cycloalkanes Intro to Hydrocarbons
    • Classes and intro to alkanes (section 2.1, 2.5)
    • Nomenclature branched & unbranched alkanes (section 2.14, 2.17)
    • Nomenclature isomers (section 2.15)
    • Nomenclature cycloalkanes (section 2.18)
    • Physical properties Alkanes (section 2.21)
    • Free radical reaction & halogenation mechanism of alkanes (section 10.4)

Week 2

  • Properties of Molecules
    • Bronsted-Lowry acidity (section 1.12)
      • Acidity trends (section 1.13, 1.14)
        • Electronegativity size and charge
        • Inductive effects
        • Hybridization
        •  Resonance
    • Lewis acids (section 1.15)
    • Bonds lengths/Bond strength (section 1.13)
  • Alkanes
    • Conformational analysis (section 3.1, 3.2)
    • Cis trans Stereo isomers (chapter 3)
      • Ethane Newman Projections (3.1, 3.2)
      • Butane

Week 3

  • Cycloalkanes
    • Ring size and strain (section 3.5)
    • Cyclopropane, cyclobutane, cyclopentane
    • Cyclohexane (section 3.7)
      • Conformational analysis
        • Drawing chairs
        • Ring flip
      • Mono substituted cyclohexene (sections 3.8, 3.9, 3.10)
        • Axial vs equatorial
      • Di substituted cyclohexene (sections 3.11, 3.12)
        • Cis/Trans isomerism
        • Preferred conformers
  • Stereochemistry
    • Stereoisomers (section 4.1)
    • Chirality and stereocenters (sections 4.2, 4.3)
    • Enantiomers (section 4.8)
      • Cahn-Ingold-Prelog Convention (R/S) (section 4.6)
      • Optical activity
    • Diastereomers
      • Cis/Trans isomers (Geometric)
    • Fischer Projections (section 4.7)

Week 4

  1.  Structure and synthesis of Alkenes
  2. IUPAC nomenclature (sections 7.1 through 7.8)
  3. Physical properties
  4. Cycloalkenes
  5. Synthesis of alkenes
    1. Dehydrohalogenation  (E1 and E2)
    1. Dehalogenation
    1. Dehydration of alcohols (stereoselectivity/regioselectivity )
    1. Substitution and elimination reactions competition
  6. Addition reactions of alkenes (section 8.1 through 8.15)
    1. Hydrogenation
    1. Electrophilic addition of hydrogen halides (Markovnikov’s Rule)
    1. Acid catalyzed hydration of alkenes
    1. Hydroboration oxidation
    1. Addition of halogens
    1. Ozonolysis
  1.  Alkynes (section sections 9.1 through 9.14)
    1. IUPAC nomenclature
    1. Physical properties
    1. Acidity and terminal alkynes
    1. Synthesis of alkynes

Weeks 5 and 6

  1. Substitution and Elimination Reactions of Alkyl Halides
    1. Alkyl Halides
      1. Nomenclature (section 5.2)
      1. Structure (section 5.6)
      1. Substitution/Elimination (sections 5.12, 5.13, 5.14, 5.15)
    1. Sn2 Substitution nucleophilic bimolecular
      1. Mechanism
        1. Arrow pushing
        1. Reaction-Energy Diagrams
        1. Stereochemistry
        1. Molecular Orbitals
      1. Examples of Sn2
      1. Factors affecting the rate of Sn2
        1. Substrate sterics
        1. Nucleophile
        1. Leaving group
        1. Solvent
    1. Sn1 Substitution nucleophilic unimolecular (sections 6.1 through 6.12)
      1. Mechanism
        1. Arrow pushing
        1. Reaction-Energy Diagrams
        1. Stereochemistry
      1. Factors affecting the rate of Sn1
        1. Substrate carbocation stability
        1. Leaving group
        1. Solvent
      1. Carbocation rearrangements
      1. Sn1 vs Sn2
    1. E1 Elimination unimolecular (section 7.12, 7.16, 7.18, 7.19
      1. Mechanism
        1. Arrow pushing
        1. Reaction-Energy Diagrams
      1. E1 vs Sn1
    1. E2 Elimination bimolecular
      1. Mechanism
        1. Arrow pushing
        1. Reaction-Energy Diagrams
        1. Transition state geometry
        1. Stereochemistry
      1. Positional Orientation (Zaitsev Rule)
        1. Alkene stability
        1. Bulky bases (Hofmann Products)
      1. E1 vs E2
      1. Substitution vs Elimination

CUMMULATIVE FINAL

This syllabus, which includes course materials and content, are subject to change without notice