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Course Content and Outcomes Guide for CH 242 Effective Spring 2021

Course Number:
CH 242
Course Title:
Organic Chemistry II
Credit Hours:
5
Lecture Hours:
40
Lecture/Lab Hours:
0
Lab Hours:
30
Special Fee:
$12.00

Course Description

Introduces radical reactions; substitution and elimination reaction mechanisms; structure and chemistry of alcohols, ethers, epoxides and their sulfur analogues; organometallic compounds; arenes and aromaticity; structure and chemistry of aromatic compounds; NMR, UV-VIS and Mass Spectroscopy; and special topics as time and interest permit. Prerequisites: CH 241. Audit available.

Addendum to Course Description

The course covers aspects of each of the following: Structure and Chemistry of Alkenes, Structure and Chemistry of Alkynes, Conjugation in Alkenes, Concerted Reactions (Diels Alder), Arenes and Aromaticity, Structure and Chemistry of Aromatic Compounds, UV-VIS Spectroscopy. Special topics are included as time and interest permits.
Prerequisite: Successful completion of Chemistry 241

Chemistry 242 is the second 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 242 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 should 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 II.
  • 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 241 or 242 depending on the campus you take the respective course at.

Stereochemistry

  • 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%),

  • Classify different types of alkene reactions as oxidation or reduction reactions, and predict the outcome of such reactions and apply stereochemical principles to predict the structure of the major product(s).(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 85%)

  • Use your knowledge of stereoisomerism and stability of reaction intermediates to predict the outcome of alkyne reactions.  (Benchmark 85%)

  • Apply knowledge of bonding theories and structure to predict the reactivity of alkynes. (Benchmark 80%)

  • Describe reactions of acid-catalyzed hydration and hydroboration of alkynes and show mechanistically that ketones and aldehydes are major products.  Explain what is meant by tautomer and draw structures that show the keto-enol interconversion. (Benchmark 75%)

  • Predict the outcome of a variety of alkyne reactions including  reduction reactions 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 80%)

The following list of topics will be covered in CH242, regardless of campus.

Nucleophilic Substitution and Elimination Reactions

  • Draw the mechanism, using curved arrow notation, for the four different types of nucleophilic substitution and elimination reactions (SN1, SN2, E1 and E2). (Benchmark 80%)

  • Predict the outcome of a variety of reactions with leaving groups and nucleophiles. (Benchmark 80%)

  • Use your knowledge of stereoisomerism to predict the outcome of substitution and elimination reactions. (Benchmark 75%)

  • Explain the terms nucleophile and leaving group and arrange a set of compounds in the order of reactivity towards substitution and elimination reactions. (Benchmark 75%)

  • Given a starting reagent and a target product propose a multi-step (minimum 3 –step) synthesis using substitution and/or elimination reactions. (Benchmark 75%)

  • Identify and explain the factors that affect substitution and elimination reactions. (Benchmark 80%)

  • Given a set of alkenes, arrange them in order of stability, and correlate this order to the heat of hydrogenation of these alkenes. (Benchmark 85%)

  • Draw all possible products for an elimination reaction and rank the products in correct stability order. (Benchmark 75%)

  • Identify the necessary lab conditions (nucleophile, leaving group, solvent, and temperature) for SN1, SN2, E1, and E2 reaction mechanisms. (Benchmark 75%)

Reactivity of Radicals

  • Draw the mechanism, using curved arrow notation, for the different types of radical reactions of alkane and alkenes and predict the outcome of such reactions. (Benchmark 75%)

  • Describe and identify the different steps in a radical reaction mechanism, including the most stable radical. (Benchmark 80%)

  • Calculate the approximate product yields of a radical halogenation reaction. (Benchmark 75%)

  • Use energy diagrams to describe a reaction mechanism and distinguish between kinetic and thermodynamic stability and label products and/or reactants as kinetically and/or thermodynamically stable. (Benchmark 85%)

  • Given a starting reagent and a target product propose a multi-step (minimum 3 –step) synthesis using electrophilic addition, substitution, elimination, and/or radical reactions. (Benchmark 75%)

  • Draw the reaction mechanism for any chain-growth polymer up to tetramers. (Benchmark 75%)

  • Classify polymers as chain-growth or step-growth mechanisms. (Benchmark 75%)

  • Predict the product for reactions between monomers. (Benchmark 75%)

Aromaticity

  • Classify molecules as aromatic, antiaromatic, or nonaromatic based on the criteria for each of these terms. (Benchmark 75%)

UV Visible Spectroscopy

  • Draw and label molecular orbital diagrams using only the p-orbitals for conjugated molecules. (Benchmark 80%)

  • Distinguish between HOMO and LUMO energy states and use these to explain the wavelength trends observed in UV-Vis Spectra. (Benchmark 85%)

  • Describe molecular orbitals of conjugated double bonds and recognize the differences (in properties and reactivity) among isolated, conjugated, and cumulated dienes.  (Benchmark 80%)

NMR Spectroscopy (In lecture or lab)

  • Draw the structure of a molecule consistent with FTIR, C-NMR, H-NMR spectra, and a given molecular formula. (Benchmark 75%)

  • Label the peaks and identify the splitting patterns in C- and H- NMR spectra. (Benchmark 80%)

  • Be able to predict the splitting pattern (spin-spin coupling, N+1 rule) in the 1H NMR spectrum of a compound given its structure.  Sketch a doublet, triplet, quartet, quintet, and multiplets with correct relative heights.   (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 85%)

  • Use environmentally friendly, microscale and macroscale organic chemistry laboratory techniques to successfully produce reliable results. (Benchmark 85%)

  • Use a combination of physical methods such as melting point, boiling points and solubility as well as qualitative chemical tests and spectroscopy (including infrared spectrometry, carbon, and proton NMR spectroscopy) to separate and analyze compounds in a mixture or from a set of reactions. (Benchmark 85%)

  • Predict the product(s) of Diels-Alder Reactions, including electrophilic additions (1,2 versus 1,4 additions), cycloaddition reactions and the stereochemistry of products.  (Benchmark 85%)

  • Successfully complete  the experimental protocol efficiently in lab, which includes  troubleshooting when problems arise.  (Benchmark 90%)

  • Write a formal written report in the form of a manuscript using a format similar to the Journal of Organic Chemistry. (Benchmark 80%) 

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%)