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The City College of New York Department of Chemistry Chemistry 26100: Organic Chemistry I Section: AB Lecture: M and W 9:00 AM – 10:50 AM Dr. Issa Salame (212) 650 – 6924 Office Location: MR1224 [email protected] ****************************************************************************** Catalog Description: An introduction to the chemistry of carbon compounds, current interpretation of the reactions and properties of these compounds. Prerequisites: Co-requisites:

Chem 10401 or 10400

Hours/Credits:

4 per week, 3 hours lecture, 1 hour recitation, 3 credits

Textbook: Organic Chemistry, David Klein, Third Edition, Wiley, 2017. Molecular models: (Dr. Darling’s) are available in the bookstore and on the internet (http://www.darlingmodels.com/KIT #1 ISBN 0-9648837-1-6). Course objectives: This course is the first of a two-semester sequence. The objective of the course is to provide introduction to organic chemistry, via discussion of reactivity, key reaction mechanisms, retrosynthetic analysis, and structure determination via IR, NMR, and MS spectroscopies. The course strives to enhance the critical thinking and the problem solving skills of the students.

After completing this course students should know: 1. Lewis structures, resonance forms, acid/base theories, orbital hybridization and geometry of molecules, functional groups, constitutional isomers, cis/trans isomers.

Department outcomes a, b

2. IUPAC nomenclature of alkanes, Newman projection formulas, cycloalkane conformations, cis/trans isomers of cycloalkanes.

a, b

3. Recognize and write structures for chiral and achiral molecules, (R) and (S) configurations, racemates, enantiomers, diastereomers, meso compounds, Fisher projection formulas.

a, b

4. Mechanism of SN1, SN2, E1 and E2 reactions. Predict the products of the substitution and elimination reactions including stereochemistry.

a, b

1

5. Predict the products of carbocation rearrangements, dehydration, dehydrohalogenation and dehalogenation reactions.

a, b

6. Predict the products of additions, oxidations, reductions and cleavages of alkenes, including regiochemistry and stereochemistry. Acetylide ions in the synthesis of alkynes.

a, b

7. Predict the products of additions, oxidations, reductions and cleavages of alkynes. Predict the products of hydration, hydroboration, and hydroxylation of alkenes. Use Grignard and organolithium reagents for the synthesis of alcohols. Reaction of alcohols and pinacol rearrangement of diols.

a, b

8. Predict the mechanism and products of radical reactions

a, b

9. Do retrosynthetic analysis to solve multistep synthesis problems

a, b

10. Interpret simple infrared and mass spectra. Use the information derived from the IR and MS spectra to propose a tentative structure for an unknown organic compound.

a, b

Topics covered: 1. Carbon Compounds and Chemical Bonds 2. Representative Carbon Compounds: Functional Groups, Infrared Spectroscopy, & Intermolecular Force 3. An Introduction to Organic Reactions: Acids and Bases 4. Alkanes: Nomenclature, Conformational Analysis, & An Intro to Synthesis 5. Stereochemistry: Chiral Molecules 6. Ionic Reactions - Nucleophilic Substitution & Elimination Reactions: Alkyl Halides 7. Alkenes & Alkynes: Properties & Synthesis, Elimination Reactions of Alkyl Halides 8. Alkenes & Alkynes II: Addition Reaction 9. Spectroscopic Methods of Structure Determination 10. Radical Reactions 11. Alcohols & Ethers 12. Alcohols from Carbonyl Compounds, Oxidation-Reduction & Organometallic Compounds Course schedule: Section: AB Lecture:

M and W: 9:00 am – 10:50 am

Relationship of course to program outcomes: The outcome of this course contribute to the following departmental educational outcomes: a.

demonstrate an understanding of the fundamental principles of chemistry, including atomic and molecular structure, quantum chemistry, chemical bonding, stoichiometry, kinetics and mechanism, equilibrium, thermochemistry and thermodynamics, molecular structure and function,

Course Objective Numbers 1-13, 16

2

b.

c. d. e. f. g. h. i. j. k.

electrochemistry, and the periodic chemical properties of the elements. apply the fundamental principles of chemistry to life sciences, the environment, materials, engineering, and emerging technological fields of chemistry, as well as to everyday situations. conduct experiments and learn fundamental laboratory skills analyze and interpret data apply mathematical concepts to chemical problems work as part of a problem-solving team convey facts, theories and results about chemistry in written form use oral presentation to convey facts, theories and results about chemistry access and utilize chemical information technology design and execute scientific research apply ethical responsibilities and professional conduct

1-13, 16

NA 12 - 14 NA 15 NA NA NA NA NA

Assessment tools: The final grade is calculated as follows: Best two scores of the three in-class examinations (50%) Final Examination (50%) * The lowest grade exam will be dropped. Missing an exam will result in receiving a zero grade for that particular exam and thus dropping that grade. There will not be any Make-up Exams. PROBLEMS: The assigned problems are a very important part of the course. You are responsible for all problems, within and at the end of each chapter. If you can do the problems, you should do well on the exams. EXAMS: There will be three 90 minute exams during the semester of which you should take at least two. If you take all three exams your lowest exam score will be dropped while computing your grade. If you take only two of the 90 minute exams, all scores will count. These three exams will account for 50% towards your final grade, and the Final Examination for 50%. The date of the Final Examination will be set by the registrar, and will cover ALL CHAPTERS (1-12) studied. Office Hours: Wednesdays: 11:30 am – 12:30 pm Thursdays: 10:00 am – 11:00 am Or by appointment via zoom Absence Policy (Attendance) Students are expected to attend every class session of each course in which they are enrolled and to be on time. An instructor has the right to drop a student from a course for excessive absence. Students are advised to determine the instructor’s policy at the first class session. They should note that an instructor may treat lateness as equivalent to absence. (No distinction is made between excused and unexcused absences.) Each instructor retains the right to establish his or her own policy, but students should be guided by the following general College policy: In courses designated as clinical, performance, laboratory or field work courses, the limit on absences is established by the individual instructor. For all other courses, the number of hours 3

absent may not exceed twice the number of contact hours the course meets per week. When a student is dropped for excessive absence, the Registrar will enter the grade of WU. Academic Integrity The CCNY policy on academic integrity will be followed in this course. The document can be found at: http://www1.ccny.cuny.edu/current/integrity.cfm In addition, the Policy on Academic Integrity can be found in the Undergraduate Bulletin 2007 - 2009 in Appendix B.3 on page 312. All students must read the details regarding plagiarism and cheating in order to be familiar with the rules of the college. Cases where academic integrity is compromised will be prosecuted according to these rules. Allowing the student to do extra work after the final grade has been awarded: A student offers the instructor many reasons why the academic work submitted during the semester was not an adequate representation of his/her grasp of the course content. The instructor agrees to read the extra work and change the grade, if the work is warranted. Although similar to the above situation in that the student is being allowed to do work after the course is over, this scenario differs in its details. This arrangement presents two problems: firstly, it is unfair to those students who have not been offered such an opportunity and have completed coursework sufficiently and on time; secondly, it circumvents the mandated appeals process. Consequently, it is a violation of the academic policy of the school. Allowing the student to negotiate a grade: A student does no extra work after the award of a final grade, yet he/she bases a campaign for a higher grade on the sheer force of an argument. The higher grade may be wrested from the professor by the brilliance of the student’s debate or by the latter’s subtle but persistent erosion of the instructor’s strength of refusal. As the instructor is paid for his/her expertise in a field, they are expected to exercise competency in his/her determination of an appropriate grade for a student. Consequently, it is a violation of the academic policy of the school. Department “INC” Grade Policy "Makeup exam for INC grades in Chemistry courses will be completed no later than two weeks after the end of classes. INC may be assigned to students who have a passing grade in the course but who are unable to take the final examination. A passing grade is computed by averaging all examinations / assignments which include a zero grade for missed examinations / assignments [or In calculating the passing grade, missed class examination / assignment is given a value of zero and included in the computation of the grade]. A student must have a very good reason (such as a conflict with another scheduled examination, death of spouse, injury sustained in a catastrophic incident, etc., and {proof is also required}) for missing the scheduled final exam and be given an INC grade. If the reason is not forthcoming, then a letter grade of F should be assigned. An Incomplete Grade Agreement form must be signed by the Instructor before the student is allowed to take the makeup exam. Payment of a fee at the Bursar's office is required in order to take the makeup examination. The Registrar may waive the fee if the reason for granting an INC grade is conflict with another scheduled examination. Grades for a makeup exam will be submitted within one week of the administration of the exam. Disability In compliance with CCNY policy and equal access laws, appropriate academic accommodations are offered for students with disabilities. Students must first register with The AccessAbility Center for reasonable academic accommodations. The AccessAbility Center is located in the North Academic Center, Rm. 1/218. Tel: (212) 650-5913. Under The Americans with Disability 4

Act, an individual with a disability is a person who has a physical or mental impairment that substantially limits one or more major life activities. If you have any such issues, I encourage you to visit the AccessAbility Center to determine which services may be appropriate for you. Courtesy Noise and excessive chatter, eating, drinking, or use of unauthorized electronic equipment is not allowed in the classroom. TEXTBOOK PROBLEMS: The assigned problems are a very important part of the course. You are responsible for all problems, within and at the end of each chapter. If you can do the problems, you should do well on the exams. Class Schedule Wednesday August 26th

Monday August 31st

Wednesday September 2nd Monday September 7th

Chapter 1. A Review of General Chemistry: Electrons, Bonds, and Molecular Properties 1

Chapter 1. A Review of General Chemistry: Electrons, Bonds, and Molecular Properties 1

Chapter 2. Molecular Representations

*** NO CLASSES *** *** LABOR DAY *** COLLEGE CLOSED ***

Wednesday September 9th

Chapter 2. Molecular Representations

Monday September 14th

Chapter 3. Acids and Bases

Wednesday September 16th

Chapter 4. Alkanes and Cycloalkanes

Monday September 21st

Chapter 4. Alkanes and Cycloalkanes

Wednesday September 23rd

Chapter 4. Alkanes and Cycloalkanes

Monday September 28th

*** NO CLASSES *** *** COLLEGE OPEN ***

5

Tuesday September 29th

Monday Schedule *** FIRST EXAMINATION ***

Wednesday September 30th

Chapter 5. Stereoisomerism

Monday October 5th

Chapter 5. Stereoisomerism

Wednesday October 7th

Chapter 6. Chemical Reactivity and Mechanisms

Monday October 12nd

Wednesday October 14th

Monday October 19th

*** NO CLASSESS **** *** COLUMBUS DAY *** COLLEGE CLOSED *** Monday Schedule Chapter 7. Alkyl Halides: Nucleophilic Substitution and Elimination Reactions

Chapter 7. Alkyl Halides: Nucleophilic Substitution and Elimination Reactions

Wednesday October 21st

Chapter 8. Addition Reactions of Alkenes

Monday October 26th

Chapter 8. Addition Reactions of Alkenes

Wednesday October 28th

Catch-up and review for Third Examination

Monday November 2nd

*** SECOND EXAMINATION ***

Wednesday November 4th

Chapter 9. Alkynes

Monday November 9th

Chapter 9. Alkynes

Wednesday November 11th

Chapter 10. Radical Reactions

Monday November 16th

Chapter 11. Synthesis 6

Wednesday November 18th

Chapter 12. Alcohols and Phenols

Monday November 23rd

Chapter 12. Alcohols and Phenols

Wednesday November 25th

Friday Schedule *** No CLASS ***

Monday November 30th

Chapter 14. Infrared Spectroscopy and Mass Spectrometry

Wednesday December 2nd

Chapter 14. Infrared Spectroscopy and Mass Spectrometry

Monday December 7th

*** THIRD EXAMINATION ***

Wednesday December 9th

Catch-up and review for Final Examination

Final Examination will be scheduled during the final exam period between Monday the 14th and Saturday the 19th of December of 2020.

Our Final Exam Date is:

12

2020

Our Final Exam Time is 8:00 – 10:15 am

“I hear, I forget. I see, I remember. I do, I understand.” Chinese proverb

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