Portland Community College | Portland, Oregon

Chemistry 241 is the first term of a one-year sequence of an Organic Chemistry course designed for science majors, chemical engineering majors, and pre-professional students. An agreement made with the State Universities in Oregon will allow students to receive upper division credit for Organic Chemistry 241, 242, and 243, upon successful completion of the ACS Organic Exam in CH 243. The aim of the year long course is to bring a realistic approach to the study of mechanisms and functional group chemistry, and to provide an emphasis on the biological environment, and medical applications of organic chemistry. Chemistry 241 is a five-credit course that meets three hours per week for lecture, three hours per week for lab, and one hour per week for recitation.

Upon completion of this course the student will be able to:

• Demonstrate an intermediate ability to use effective written and/or oral communication through the application of organic chemistry concepts and reasoning using the language of chemistry. 
• Demonstrate a basic understanding of how organic chemistry impacts the natural and technological environments.
• Demonstrate an intermediate ability to use detailed data collection and analysis in order to explore organic chemical principles, effectively communicate, and critically evaluate results in the context of the material covered in Organic Chemistry I.
• Demonstrate a basic understanding of organic chemistry principles to effectively solve problems encountered in everyday life and in science using appropriate computational skills.

Core Outcome 4: Cultural Awareness

Demonstrate appropriate cultural awareness within the organic chemistry field.

Core Outcome 6:  Self Reflection

Demonstrate effective self-reflective skills within the organic chemistry field.

The entire course promotes different types of learning: active, collaborative, and independent learning. The lecture portion of this class is designed to stimulate interest in the subject and promotes active, collaborative, and independent learning. The laboratory utilizes microscale equipment, modern analytical instrumentation, and the application of typical laboratory procedures. The lab portion of this class is used to promote both collaborative and active learning in a lab setting and engage the student in the world of science through individual research projects. The recitation portion of this class, through team learning, focuses on small group problem solving.
 

PCC Core Outcome Mapping: Core Outcome Communication - Mapping Level Indicator 3

Demonstrate an intermediate ability to use effective written and/or oral communication through the application of organic chemistry concepts and reasoning using the language of chemistry. 

PCC Core Outcome Mapping: Core Outcome Community and Environmental Responsibility - Mapping Level Indicator 2

Demonstrate a basic understanding of how organic chemistry impacts the natural and technological environments.

PCC Core Outcome Mapping: Core Outcome Critical Thinking - Mapping Level Indicator 3

Demonstrate an intermediate ability to use detailed data collection and analysis in order to explore organic chemical principles, effectively communicate, and critically evaluate results.

PCC Core Outcome Mapping: Core Outcome Professional Competency - Mapping Level Indicator 2

Demonstrate a basic understanding of organic chemistry principles to effectively solve problems encountered in everyday life and in science using appropriate computational skills.

General

At the beginning of this course, the instructor will detail the methods used to evaluate student progress and the criteria for assigning a course grade.  These methods will include:

• Written homework assignments designed to promote integration and analysis of lecture material
• Quizzes and/or exams that include multiple choice, short answer and essay questions to integrate, apply, and critically evaluate material covered in the class
• In class collaboration through small group activities
• Written laboratory reports and oral or written presentation of research projects to demonstrate application of the scientific method and the proper use of peer-reviewed sources. 
• Completion of assigned laboratory work as demonstrated by proper documentation of experiments in a lab notebook. 

Introduction to the Study of Organic Chemistry 

• Identify molecular geometry, shape, polarity, and hybridization of structures as applied to organic compounds. (Benchmark 100%)

• Draw a set of resonance structures showing movement of electrons and identify the most stable structure in a set. (Benchmark 90%)

• Use curved arrow notation to properly follow electron flow in chemical reactions and resonance structures. (Benchmark 85%)

• Determine acid-base strength by ranking a set of molecules in order of acid strength, base strength, or pKa values and predict the strength of an acid or base based on structural features such as inductive effects, size of an atom, electronegativity, hybridization, and/or resonance effects. (Benchmark 85%)

• Use pKa and/or your knowledge of acid-base strength to predict the outcome of both Lewis and Bronsted acid-base reactions. (Benchmark 85%)

• Given the structure of a molecule, determine the IMF’s present and rank physical properties such as bp, mp, and/or solubility in a series of molecules based on the strength of the intermolecular forces (IMFs). (Benchmark 90%)

• Draw and recognize functional groups, and show how structures of compounds relate to their physical and chemical properties. (Benchmark 85%)

• Predict the relative differences in boiling points, melting points, and water solubilities for the various families of common organic compounds. (Benchmark 85%)  

Nomenclature and Structure Writing

• Use the language of organic nomenclature rules to properly name alkanes, alkenes, alkynes, alcohols, alkyl halides, ethers, and amines and draw structures using different types of structural presentations. (Benchmark 85%)

• Label an alkyl halide, alcohol, or amine as primary (1°), secondary (2°), or tertiary (3°). (Benchmark 95%)

• Draw chair representations of cyclohexanes and identify the axial and equatorial positions, and determine the most stable chair conformation for substituted cyclohexane molecules. (Benchmark 75%)

• Sketch conformations of alkanes and cycloalkanes using perspective representations such as sawhorse, Newman, and Fischer. (Benchmark 75%)

• Differentiate between the three types of strain (torsional strain, steric strain and angle strain) that contribute to the stability of cyclic compounds. (Benchmark 85%)

Alkenes, Structure, and Reactivity

• Define nucleophile and electrophile, explain their relationship to acids and bases, and classify compounds as behaving as a nucleophile or an electrophile.  (Benchmark 90%)

• Draw the mechanism, using curved arrow notation, for the different types of electrophilic addition reactions of alkenes and predict the outcome of such reactions. (Benchmark 85%) 

• Describe the evidence for the existence of carbocations, their relative stabilities, and predict when a carbocation rearrangement will occur and the product that will be formed based on rearrangements such as 1,2-Hydride shift, 1,2-Methyl shift , or ring expansion.  (Benchmark 70%) 

• Describe the mechanism in terms of a reaction coordinate diagram and be able to label the intermediate, transition states, and the rate-determining step and decide whether the reaction is exergonic or endergonic. (Benchmark 85%)

• Predict the outcome for the different types of alkene electrophilic addition reactions and predict the stereochemistry of the product(s) arising from such reactions using reaction mechanisms and the stability of reaction intermediates to explain the stereochemical outcome of the transformations. (syn vs. anti-addition) and E/Z reactant designation. (Benchmark 75%)

Isomerism

• Define isomerism and identify a set of compounds as conformers, constitutional isomers, and stereoisomers.  (Benchmark 85%)

• Use the Cahn-Ingold-Prelog priority rules to rank a set of substituents in order of group priority and given an alkene structure assign each double-bond as E,Z, cis, trans, or neither E nor Z. (Benchmark 90%)

• Classify alkene electrophilic addition reactions  as regioselective (Markovnikov or Anti-Markovnikov) or stereoselective (syn- or anti-addition).  (Benchmark 80%)

The Organic Laboratory

• Keep an up-to-date laboratory notebook and be able to communicate results and ideas effectively in writing through a carefully drafted discussion and conclusion. (Benchmark 80%)

• Use environmentally-friendly microscale and/or macroscale organic chemistry laboratory techniques to successfully produce reliable experimental results. (Benchmark 80%)

• Use  a combination of laboratory techniques including melting points, boiling points, solubility as well as qualitative chemical tests, simple and fractional distillations, steam distillation, refractive index, and infrared spectroscopy to separate and analyze compounds in a mixture or from a set of reactions.  (Benchmark 80%)

• Successfully complete  the experimental protocol efficiently in lab, which includes  troubleshooting when problems arise.  (Benchmark 85%)

• Identify and label the major functional group peaks in the infrared spectrum for alkanes, alkenes, alkynes, alcohols, amines, esters, ethers, carboxylic acids and other carbonyl-containing compounds. Use this information to match infrared spectra with the corresponding molecular structures (Benchmark 80%)

Choose one of the following:

• Write a formal written report in the form of a manuscript using a format similar to the Journal of Organic Chemistry. (Benchmark 75%) 

OR

• Complete a literature search and deliver an oral presentation on a topic related to organic chemistry.  (Benchmark 80%)

The following list of topics may be covered in CH 241 or 242 depending on the campus you take the respective course at.

• Be able to define and give an example for each of the following terms:  superimposable, chiral, achiral, chiral carbon, asymmetric carbon, stereocenter, stereoisomers, enantiomers, diastereomers, chirality, optical isomers, meso compound, racemic mixture and tautomers. (Benchmark 85%)

Alkynes, Structure and Reactivity

• Draw the mechanism, using curved arrow notation, for the different types of electrophilic addition reactions of alkynes and predict the outcome of such reactions. (Benchmark 80%) 

• Use your knowledge of stereoisomerism and stability of reaction intermediates to predict the outcome of alkyne reactions. (Benchmark 80%)

• Apply knowledge of bonding theories and structure to predict the reactivity of alkynes. (Benchmark 90%)

• Describe reactions of acid-catalyzed hydration and hydroboration of alkynes and show mechanistically that ketones and aldehydes are major products. (Benchmark 80%)

• Explain what is meant by tautomer and draw structures that show the keto-enol interconversion. (Benchmark 80%)

• Predict the outcome of a variety of reactions of alkynes such as reduction to produce alkanes or alkenes, addition reactions, and substitution reactions. (Benchmark 75%)

• Explain the higher acidity of alkynes relative to that of alkenes and alkanes, and arrange a given set of organic functional groups in order of their acidity. (Benchmark 85%)