Ch231 Organic Chemistry I

Ch231 Organic Chemistry I

Ch231 – Organic Chemistry I

Prof. Ruben Savizky

Email:

Telephone: (212) 353-4372

Class Hours: Thursday 11-1, Friday 1-2 (Room 105)

Office Hours: TBD. The best times to find me are right before or after class. If you would like to set up an appointment just email me. Room Number: NAB 413

Text:Klein, Organic Chemistry, 1st edition (Wiley), 2012

Topics to be covered:

  1. Structure and bonding
  2. Polar covalent bonds; acids and bases
  3. Overview of organic reactions
  4. Alkanes
  5. Cycloalkanes
  6. Stereochemistry
  7. Alkenes
  8. Alkynes
  9. Halides
  10. Nucleophilic substitutions and eliminations
  11. Alcohols, phenols, ethers, epoxides, thiols and sulfides
  12. Synthesis

Exams: There will be two exams (2 hours, 100 points each), and the final (3 hours, 100 points). There are NO make-up exams. They will be cumulative in the sense that the material from later in the course will rely on your understanding of concepts introduced earlier on. For each exam you will be provided with a reference sheet – a copy will be given to you before the exam so you will see the information that is on it. You will be allowed to use a scientific or graphing calculator.

Homework: Problem sets will generally be assigned at the end of each chapter. They will be graded and/or discussed.The problem sets will emphasize the concepts you learn in the course. Throughout the semester I will also assign readings from the primary scientific literature as well as computational projects using SPARTAN. These will attempt to show you applications of the concepts. For the literature readings, you will be given an article from the chemical literature and will be given one week to read it. You will also be expected to write a brief (one to four page) summary, which should include a brief synopsis of the paper, why it is significant, as well as the pros and cons of the experiment/technique/approach. We will then discuss the paper in class the following week. For the SPARTAN projects, you will also be given a week or two to complete each assignment. You will be expected to write a brief “lab report” of your findings. Your report should contain the basic elements of a technical paper: abstract, introduction, procedure, results, conclusion, and references.

Class participation: Please show respect and courtesy to me and your classmates. Do not talk or engage in distracting behavior during class. You will not be allowed to use any electronic device except a calculator – i.e. no laptop, iPad, Kindle, cell phone, etc.If you bring a cell phone to class, please silence it during class. Absolutely no text messaging or talking on the phone will be permitted during class.If you are caught using any electronic device (besides a calculator), making/receiving calls or checking/sending text messages during class, 5 points will be deducted from your calculated final grade for each violation. If behavior becomes an issue, you will be asked to leave.

Academic Dishonesty: Academic Dishonesty will not be tolerated. If you are caught cheating on any assignment or test for this course, you will fail the course and be reported for possible disciplinary probation, suspension, or expulsion from the college. Please note: If you are caught sending or receiving text messages during the exam, I will assume that you are cheating.

Grades: Your grade will be determined as follows:

Homeworks:30%

Exam 1:20%

Exam 2:20%

Exam 3:30%

Each student’s raw score will be calculated using the weighted average above. All the scores will be normalized (i.e. out of 100) and grades will be determined by cluster analysis.

Tentative schedule:“The best-laid schemes o' mice an' men / Gang aft agley” – Robert Burns, "To a Mouse, on Turning Her Up in Her Nest with the Plough" (1785)

Date / Topic / Chapter
Review: Structure, bonding, molecular orbitals and hybridization
SPARTAN Project:Acrylonitrile / 1
9/6 / Molecular representations / 2
9/7 / Molecular representations (continued)
9/13 / Acids and bases / 3
9/14 / Acids and bases (continued)
SPARTAN Project:Acidities of carboxylic acids
9/20 / Alkanes and cycloalkanes / 4
9/21 / Alkanes and cycloalkanes (continued)
SPARTAN Project:Internal rotation in dimethylperoxide and substituted cyclohexanes
9/27 / Stereochemistry / 5
9/28 / Stereochemistry (continued)
10/4 / Chemical reactivity and mechanisms / 6
10/5 / Chemical reactivity and mechanisms (continued)
10/11 / EXAM 1
10/12 / Substitution reactions / 7
10/18 / Substitution reactions (continued)
SPARTAN Project:SN2 reactions of bromide and alkyl chlorides
10/19 / Alkenes: Reactions and synthesis / 8
10/25 / Alkenes: Reactions and synthesis (continued)
10/26 / Alkenes: Reactions and synthesis (continued) / 9
11/1 / Alkenes: Reactions and synthesis (continued)
11/2 / Alkenes: Reactions and synthesis (continued)
Journal article:Dong,G.et al., Science, 2011, 333, 1609 / 9
11/8 / Alkynes / 10
11/9 / Radical reactions / 11
11/15 / EXAM 2
11/16 / Radical reactions (continued)
SPARTAN Project:3-cyano-4-methylcyclohexenyl and other radicals
11/20 / Synthesis and retrosynthesis / 12
11/21 / Synthesis and retrosynthesis (continued)
11/29 / Alcohols and phenols / 13
11/30 / Alcohols and phenols (continued)
12/6 / Ethers, epoxides, thiols and sulfides / 14
12/7 / Ethers, epoxides, thiols and sulfides (continued)
TBD / EXAM 3