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CCOG for CH 243 Summer 2022

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Course Number:
CH 243
Course Title:
Organic Chemistry III
Credit Hours:
5
Lecture Hours:
40
Lecture/Lab Hours:
0
Lab Hours:
30

Course Description

Introduces carboxylic acids, carboxylic acid derivatives, amines, carbohydrates, amino acids, proteins, lipids, nucleic acids, heterocyclic compounds, spectroscopy and selected topics. This is the third course in a three course sequence. Prerequisites: CH 242. Audit available.

Addendum to Course Description

Chemistry 243 is the third 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 243 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.

Intended Outcomes for the course

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 material covered in Organic Chemistry III.
  • Demonstrate a basic understanding of organic chemistry principles to effectively solve problems encountered in everyday life and in science using appropriate computational skills.

Aspirational Goals

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.

Course Activities and Design

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.

Outcome Assessment Strategies

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 and Problem Solving - 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. 

Course Content (Themes, Concepts, Issues and Skills)

The following list of topics may be covered in CH 242 or 243 depending on the campus you take the respective course at.

Mass Spectrometry

  • Given a mass spectrum identify the presence of Br, Cl, I, N, and/or S in a compound. (Benchmark 90%) 

  • Draw the molecular formula of a compound given a mass spectrum. (Benchmark 75%) 

  • Draw homolytic and heterolytic fragmentation mechanisms to explain the major peaks in a given mass spectrum. (Benchmark 85%) 

  • Describe the unique fragmentation for alcohols and ketones. (Benchmark 75%) 

Organometallic Reagents

  • Describe the preparation of and use of Li and Mg based organometallic reagents. (Benchmark 80%) 

  • Draw the mechanism, using curved arrow notation, for the different types of organometallic reactions involving Li, MgX and R2CuLi and predict the outcome of such reactions. (Benchmark 80%) 

  • Describe the differences in reactivity for organometallics involving Li, MgX or and R2CuLi and predict the outcome of reactions with electrophiles. (Benchmark 80%) 

Nomenclature and Structure Writing

  • Use the language of organic nomenclature rules to properly name and draw structures using different types of structural presentations for aldehydes, ketones, carboxylic acids, as well as names of common benzene derivatives.  (Benchmark 80%) 

  • Use the language of organic nomenclature rules to properly name and draw structures using ortho-, meta-, para- nomenclature for substituents on a benzene ring. (Benchmark 90%) 

  • Use nomenclature priorities for complex organic structures containing more than one functional group. (Benchmark 75%)

Electrophilic Aromatic Substitution (EAS)

  • Define electrophilic aromatic substitution (EAS) and explain the reaction mechanism of a strong electrophile to benzene. (Benchmark 80%) 

  • Draw the mechanism, using curved arrow notation, for the different types of electrophilic addition reactions of aromatic rings and predict the outcome of such reactions. (Benchmark 75%) 

  • Use energy diagrams to describe an EAS reaction mechanism and distinguish between kinetic and thermodynamic stability of the EAS reactions and label products and/or reactants as kinetically and/or thermodynamically stable. (Benchmark 80%) 

  • Draw the mechanism for the electrophilic aromatic substitution in terms of a reaction coordinate diagram. Label and identify the structure of the intermediate. (Benchmark 90%) 

  • Predict the outcome for the different types of EAS reactions including the use of Electron Donating Groups (EDGs) and Electron Withdrawing Groups (EWGs) of aromatic compounds. (Benchmark 80%) 

  • Demonstrate the ortho, para and meta directing effects of EAS reactions by drawing resonance structures and explaining them. (Benchmark 85%) 

  • Describe the limitations of Friedel-Craft reactions and use synthetic alternatives to draw multistep synthetic routes. (Benchmark 75%) 

  • Distinguish between EAS activators and deactivators and describe the result when these are in competition. (Benchmark 80%) 

  • Describe the effect of an electron withdrawing or donating group on the pKa of hydrogen atoms on an aromatic ring. (Benchmark 85%) 

  • Demonstrate an understanding of acidity and pKa by ranking a set of aromatic compounds from most acidic to least acidic. (Benchmark 85%) 

Nucleophilic Aromatic Substitution (NAS)

  • Define nucleophilic aromatic substitution (NAS) and explain the reaction of nucleophiles with benzene. (Benchmark 80%) 

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

  • Use energy diagrams to describe an NAS reaction mechanism and distinguish between kinetic and thermodynamic stability of the NAS reactions and label products and/or reactants as kinetically and/or thermodynamically stable. (Benchmark 90%) 

  • Describe the NAS mechanism in terms of a reaction coordinate diagram and be able to label the intermediate. (Benchmark 90%) 

  • Predict the outcome for the different types of NAS reactions including the use of Electron Donating Groups (EDGs) and Electron Withdrawing Groups (EWGs) of aromatic compounds. (Benchmark 75%) 

  • Demonstrate the ortho-, para- and meta- directing effects of NAS reactions by drawing resonance structures and explaining them. (Benchmark 85%) 

Nucleophilic Addition to Carbonyl Compounds

  • Draw an example of an α,β-Unsaturated Carbonyl and describe the difference between a 1,4-addition and 1,2- addition product in terms of the reactants used. (Benchmark 75%) 

  • Draw the mechanism, using curved arrow notation, for the different types of  1,4-addition and 1,2- addition products and predict the outcome of such reactions. (Benchmark 75%) 

  • Use energy diagrams to describe 1,4-addition and 1,2- addition product mechanism and distinguish between kinetic and thermodynamic stability of the 1,4-addition and 1,2- addition product reactions and label products and/or reactants as kinetically and/or thermodynamically stable.  (Benchmark 90%) 

  • Draw the mechanism, using curved arrow notation, for the reaction in which an aldehyde can be converted to an alcohol.  (Benchmark 80%) 

  • Describe the effect of Le Chatelier’s Principle to equilibrium reactions in hydrate, hemiacetal and acetal formation.   (Benchmark 85%) 

  • Draw the mechanism, using curved arrow notation, and be able to predict the products for reactions involving the formation of an imine, enamine and acetal.  (Benchmark 75%) 

Reactivity of Carboxylic Acids, Amides, Acid Halides and Acid Anhydrides

  • Describe the reactivity of carboxylic acid with a nucleophile(including reduction reactions).  (Benchmark 85%) 

  • Draw the mechanism, using curved arrow notation, for the reaction in which a carboxylic acid forms an ester and the acid or base hydrolysis of an ester to a carboxylic acid.  (Benchmark 75%) 

  • Draw the products of the following reactions: transesterification, formation of an amide from a carboxylic acid, acid or base amide hydrolysis, nitrile hydrolysis. (Benchmark 75%) 

  • Draw the mechanism, using curved arrow notation, for the reaction in which an acid halide undergoes nucleophilic acyl substitution.  (Benchmark 80%) 

  • Given an acid halide or anhydride, draw the products of reactions with the following reagents: amines, water, alcohols, lithium or magnensium type Grignard reagents, dialkyl curprate reagents, and the reducing agents NaBH4 and LiAlH4. (Benchmark 80%) 

Enolate and Enol Nucleophiles

  • Determine the most acidic hydrogen present in a carbonyl compound and explain why. (Benchmark 90%) 

  • Draw the mechanism, using curved arrow notation, for the reaction of an enolate ion with a methyl or primary alkyl halide and predict the outcome of such reactions. (Benchmark 75%) 

  • Draw the mechanism, using curved arrow notation, for the reaction of an enol in acid catalyzed alpha-halogenation and predict the outcome of such reactions. (Benchmark 75%) 

Reactions at the α-Carbon

  • Draw the mechanism, using curved arrow notation, for the base catalyzed aldol reaction involving aldehydes and ketones.  (Benchmark 75%) 

  • Use energy diagrams to describe the difference in reactivity of aldehydes and ketones in aldol reactions.   (Benchmark 90%) 

  • Demonstrate an understanding of aldehydes and ketones as electrophiles and nucleophiles and their relative strengths by predicting the products of aldol reactions. (Benchmark 80%) 

  • Draw the mechanism, using curved arrow notation, for the dehydration (elimination) after a either a base or acid catalyzed aldol reaction forming the aldol condensation product.  (Benchmark 80%) 

  • Predict the product(s) for α substitution in aldehydes, ketones, and β-diketones and β-diesters followed by decarboxylation. (Benchmark 75%) 

Multi-step Synthesis

  • Determine the correct multi-step reaction sequence given a starting molecule and a target molecule using reactions listed in previous objective and including: converting a nitro group to an amino group, oxidizing an alkyl group to a carboxylic acid, acylation and de-acylation of anilines, sulfonation and de-sulfonation of aromatic rings, and protecting groups (specifically cyclic acetal). (Benchmark 75%) 

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 90%) 

  • Use environmentally- friendly microscale and/or macroscale organic chemistry laboratory techniques to successfully produce reliable experimental results (Benchmark 90%) 

  • Using of environmentally friendly and microscale and macroscale organic chemistry laboratory techniques to successfully produce reliable results. (Benchmark 90%) 

  • Using a combination of physical methods such as melting point, boiling points and solubility as well as qualitative chemical tests and spectroscopy (including infrared spectrometry, proton NMR spectroscopy and Mass Spectrometry) to separate and analyze compounds in a mixture or from a set of reactions. (Benchmark 90%) 

  • Perform the experimental protocol in lab and be able to troubleshoot when problems arise.  (Benchmark 95%) 

  • Write formal written reports in the form of a manuscript (using the format of a Journal of Organic Chemistry manuscript).  (Benchmark 85%) 

  • Complete, design, and orally present an independent organic research project that utilizes a combination of the experimental techniques learned in the year-long organic chemistry sequence. In the design of this project, students need to obtain accurate safety and waste disposal procedures for all compounds utilized and synthesized in the project. (Benchmark 85%)