CHEM 2323 - Organic Chemistry I Lecture
Syllabus for In-Person Class
Fall 2024

Instructor: Dr. Debbie Sackett
e-mail address: dsackett@austincc.edu
office: RGC 1333.03 (building 1000, enter through 1333.00)
office phone number: 512-223-3314

              COURSE DESCRIPTION

An introduction to the chemistry of carbon compounds. An integration of aromatic and aliphatic compounds treating the principal classes of each. Emphasis on molecular structure theory, stereochemistry, structure and reactivity, and reaction mechanisms.

Prerequisites: CHEM 1412 or equivalent. Students who do not have the proper prerequisites will be dropped from the class. Student may be required to show proof of prerequisites by uploading transcripts or CLEP test scores. Refer to the announcement in Blackboard. Students who do not have the proper prerequisites will be dropped from the class.

Co-requisite: CHEM 2123

Instructional Methodology – This is an in-person lecture.

Course Rationale: This course covers the fundamental facts; laws, principles, theories and concepts of chemistry necessary for further work in science or science related subjects.

COURSE MATERIALS

Textbook: "Organic Chemistry", 8th ed., by Bruice is the departmental text. You are free to use a current or older version of this text, or another book altogether. I personally like the book by Bruice. Do not attempt this course without a college-level textbook of some sort.

Molecular models: Molecular models are suggested, but not required for this course. The following sets are recommended for their quality and are available from a variety of online sources:

• Framework Molecular Models (from www.chemkits.com)
• Prentice Hall Molecular Model Set for Organic Chemistry

I created a short video illustrating the pros/cons of each model type. It is located in the FAQ folder of Blackboard.

Internet and computer access: You will need to have internet access in order to watch recorded lecture videos (optional). You will need to print lecture outlines and perhaps homework assignments. Everything can be accomplished on campus.

COURSEWORK AND GRADED COMPONENTS

Lecture Notes: An outline of the lecture notes for students can be found in Blackboard. Once a unit of material is complete, the instructor’s copy of the notes (with all of the information filled in) will be posted.

Lectures will be delivered during the schedule class time. Students can print the outlines and fill in the notes during lecture. Another option is that a student can simply watch the lectures, and print or study from the instructor completed notes at the end of a unit.

Practice Problems: Practice problems will be assigned for each unit, but not graded. Exam questions will come from the practice, homework, and lecture notes. Working the problems is strongly encouraged. Answer keys to the practice problems are posted in Blackboard.

Homework: There will be 19 graded homework assignments; one or two per week. Each assignment will be worth 5 points. Your homework grade will be based on the 15 highest grades, totaling 75 possible points or 12.5% of your final grade. You will be expected to upload your work/answers as a pdf file. More specific instructions will be provided in Blackboard.

Orientation Quiz: There will be a mandatory orientation quiz that must be completed in order to remain registered in the class. This quiz is worth 9 points.

Other Quizzes: There will be 4 additional quizzes throughout the semester. These are worth 9 points each. They are untimed and not monitored. You are expected and encouraged to work together and look for outside resources to help you with these activities. I can help with the quizzes, but only in a general way.

The total possible score for the quizzes is 45 points or 7.5% of your grade.

Exam Review Assignments: Immediately following the completion of material for an exam, a set of review problems will deploy. You will submit answers via a link in Blackboard. Upon submission, the answer key and a video explanation will deploy. There is a total of 5 review assignments. These are largely graded on completion, rather than accuracy. Each is worth 6 points. The total is 30 points or 5% of your grade.

Exams: There will be five regular exams, each worth 90 points. These exams will be given in class on the tentative dates shown below. Dates may change if college closure(s) directly affect the class.

If you miss an exam, you must contact me as soon as possible in order to arrange a makeup. This will very likely be offered through the testing center, no more than two days after the scheduled exam date. You must have a compelling, documented reason for missing the exam (e.g., hospitalization or incarceration).

There is a comprehensive final, worth 90 points. The final exam is optional. You can take this exam if you wish to replace a lower grade on a previous exam with the grade from the final exam. If you take the final exam and it is your lowest grade, it will be the dropped grade.

GRADING

Your final grade is based on your 5 highest exam grades, your 15 highest homework grades, quizzes and exam review assignments. There is no alternative to these grades or extra credit.

A standard scale will be used to assign a final grade in the class, as illustrated in the table below.

LECTURE OUTLINE, TEXTBOOK REFERENCES & CALENDAR

*Test dates are tentative and will be confirmed/changed with an announcement on Blackboard.

Unit/Title                                                                              Textbook reference

Unit 1: General Chemistry Review.......................................1.1-1.8, 1.14-1.16, 2.1- 2.5, 2.12, 8.3-8.5
Unit 2: Introduction to Hydrocarbons..........................................1.6-1.9, 1.11-1.13, 2.6-2.10, 3.1-3.3
Exam 1 (Sept. 18)

Unit 3: Conformations of Alkanes and Cycloalkanes..........................................................3.11-3.15
Unit 4: Stereochemistry...............................................................................4.1-4.10, 4.12-4.15
Unit 5: Alkyl Halides from Free Radical Substitution............................3.4, 5.4-5.6, 5.8, 12.1-12.5, 12.8
Exam 2 (Oct. 14)

Unit 6: Alcohols and Alkyl Halides: Nucleophilic Substitution.............................9.1-9.5, 9.14, 10.1-10.3
Unit 7: Structure and Preparation of Alkenes: Elimination Reactions...4.2, 5.1-5.3, 5.9, 9.6-9.12, 9.15, 10.4
Exam 3 (Nov. 3)

Unit 8: Reactions of Alkenes: Addition Reactions..............5.5, 5.7, 5.12, 6.1-6.5, 6.7, 6.9-6.13, 6.16, 12.7
Unit 9: Alkynes.............................................................................................7.1-7.7, 7.9-7.12
Unit 10: Conjugated Systems............................................................8.4-8.9, 8.12, 8.13, 9.13, 12.9
Exam 4 (Nov. 25)

Unit 11: Arenes and Aromaticity........................................8.1-8.3, 8.11, 8.16-8.20, 12.9, 18.10, 18.11
Unit 12: Electrophilic Aromatic Substitution............................................8.21, 18.1-18.8, 18.12-18.17
Exam 5 (Dec. 9)

Comprehensive Final (Dec. 11)

Other important dates include:
Last day to drop without receiving a ‘W’ on your transcript: 9/11/24
Last day to withdraw from the class: 11/21/24

GENERAL COURSE INFORMATION AND POLICIES

Attendance Policy: You are not required to attend lecture; however, your life will be so much easier if you do attend class.

Academic Integrity: Consider the following guidelines when accessing information for this class.

Homework, quizzes and review assignments: You may use all manner of resources to complete these activities. My goal is for you to collaborate with each other and to find resources (in addition to me) to help you be successful.

Exams: You are to use your knowledge and a limited amount of class materials (defined within the exam preparation folder in Blackboard).

Incomplete Grade Policy: An instructor may award a grade of “I” (Incomplete) if a student was unable to complete all of the objectives for the passing grade in a course due to medical/emergency reasons. Incompletes can be given if you complete 75% of the course work with at least a 70% average. An incomplete grade cannot be carried beyond the established date in the following semester. The completion date is determined by the instructor but may not be later than the final deadline for withdrawal in the subsequent semester.

Withdrawal Policy: It is the responsibility of each student to ensure that his or her name is removed from the roll should he or she decides to withdraw from the class. The instructor will not drop students, except if the student:

• does not have the proper prerequisites for the class
• has not successfully completed the orientation quiz by the deadline

If a student decides to withdraw, he or she should also verify that the withdrawal is submitted before the Final Withdrawal Date. The student is also strongly encouraged to retain their copy of the withdrawal form for their records. Students who enroll for the third or subsequent time in a course taken since Fall 2002, may be charged a higher tuition rate, for that course. State law permits students to withdraw from no more than six courses during their entire undergraduate career at Texas public colleges or universities. With certain exceptions, all course withdrawals automatically count towards this limit. Details regarding this policy can be found in the ACC college catalog.

The drop deadline is November 21,2024. The lecture and the lab are required in each chemistry course. If a student drops/withdraws from one section of the course, they must drop/withdraw from the corequisite.

If you stop attending class and do not withdraw yourself from the course, you will receive a grade of F for the semester. Reinstatement into a course after withdrawing is only possible if the student was withdrawn through college error. 

COMMON COURSE OBJECTIVES

Fundamentals: The Basics

• Atomic structural theory, Lewis structures, Formal charges, constitutional isomers, basic resonance theory
• Atomic, molecular, and hybrid orbitals, covalent bonding, shapes of molecules
• Polarity of molecules and bonds
• Physical properties and intermolecular forces
• Functional groups and families of organic compounds
• Acid and base properties, equilibria, and relative acid/base strengths, structural features affecting acidity (e.g., inductive effects, resonance, hybridization, etc.), selection of appropriate conjugate base for H removal
• Evaluate nucleophilic strength
• Potential energy diagrams of reactions, activation energies of reactions

Introduction to Mechanisms and Synthesis:

• Introduction to mechanisms
• Curved arrow notation
• Basic retrosynthetic analysis
• Synthesis of alkanes, alkenes, alkynes, and aromatic compounds
• Hammond Postulate

Organic Nomenclature

• IUPAC Nomenclature of alkanes, cycloalkanes, bicycloalkanes, alkenes, cycloalkenes, alkynes, alkyl halides, and aromatic compounds
• R/S Nomenclature system for chiral molecules
• E/Z Nomenclature system for alkenes

Stereochemistry

• Chirality
• Optical activity, specific rotation, optical purity, enantiomeric excess
• Enantiomers, diastereomers, meso compounds
• Stereoisomerism of cyclic compounds
• Stereochemistry in reactions
• Resolution of a racemic mixture

Hydrocarbons (Alkanes, cycloalkanes, alkenes, alkynes, dienes, and aromatics)

• Structure and physical properties
• Ring strain and conformations of cycloalkanes
• Conformational analysis of ethane and higher alkanes
• Cyclohexane- chair, boat, axial/equatorial positions, “flipping” between conformations
• Relative stabilities of alkenes and alkynes

Reactions and Their Mechanisms

• Nucleophilic substitution reactions (SN2 and SN1)
• Elimination reactions (E2 and E1)
• Homolytic bond dissociation Energies
• Free radical reactions, halogenation of alkanes, radical addition to alkenes
• Halogens and selectivity
• Hydrogenation of alkenes and alkynes
• Reduction of alkyl halides
• Alkylation of terminal alkynes
• Dehydrohalogenation of alkyl halides, Zaitsev and Hofmann rules
• Dehydration of alcohols
• Rearrangements of carbocation intermediates
• Debromination of vicinal dibromides
• Markovnikov’s rule and anti-Markovnikov’s reactions (Peroxide effect); Regioselectivity
• Addition of hydrogen halides, sulfuric acid, water, and halogens to alkenes and alkynes
• Stereospecific reactions
• Formation of halohydrins
• Oxidations of alkenes and alkynes, syn-hydroxylation, oxidative cleavage, ozonolysis
• Stability of allylic radicals and cations
• Conjugated dienes; their stabilities
• Resonance theory
• Allylic substitution
• 1, 2 and 1, 4 addition reactions; The Diels-Alder Reactions
• Aromaticity of benzene and other aromatic compounds
• Huckel’s Rule
• Antiaromatic, and Nonaromatic compounds
• Electrophilic aromatic substitution reactions, halogenation, nitration, sulfonation, Friedel- Crafts alkylation, Friedel-Crafts acylation, effects of substitutents on reactivity and orientation
• Reactions of alkyl side chains on aromatic rings, benzylic halogenation, addition to alkenyl benzenes, oxidation of alkyl side chains

STUDENT LEARNING OUTCOMES

Upon successful completion of this course, students will:

1. understand the structure and bonding of organic molecules
2. understand the nomenclature of aliphatic and aromatic compounds
3. understand conformational structures of alkanes
4. recognize and assign stereochemical designations of organic compounds
5. predict products from reactions of alkenes, alkynes, alkyl halides, dienes, and aromatic compounds based on a mechanistic understanding of these reactions and apply these reactions in multi-step syntheses

GENERAL EDUCATION COMPETENCIES

Upon completion of this course, students will demonstrate competence in:

• Critical Thinking

Gathering, analyzing, synthesizing, evaluating and applying information.

• Interpersonal Skills

Interacting collaboratively to achieve common goals.

• Quantitative and Empirical Reasoning

Applying mathematical, logical and scientific principles and methods.

• Technology Skills

Using appropriate technology to retrieve, manage, analyze, and present information.

• Written, Oral and Visual Communication
  Communicating effectively, adapting to purpose, structure, audience, and media

The information for this section is listed in the syllabus above.

The information for this section is listed in the syllabus above.

The information for this section is listed in the syllabus above.