Aug 14, 2022  
College Catalog 2022-2023 
    
College Catalog 2022-2023
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CHEM 2280 - Organic Chemistry 2

Credit Hours: 4.00


Prerequisites: CHEM 2260  with grade C or better

This course is a continuation of CHEM 2260. Electrophilic and nucleophilic aromatic reactions are explored. The chemistry of the functional groups (alcohols, aldehydes, ketones, acids, acid derivatives, ethers, amines, thiols, etc.) is studied with a continuing emphasis on mechanisms. Organic synthesis is also a major theme of this course, including the role of carbanions.

Billable Contact Hours: 4

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OUTCOMES AND OBJECTIVES
Outcome 1: Upon completion of this course, students will be able to demonstrate a working knowledge of the preparation and reactions of compounds containing polyenes and allylic functionalities.

Objectives: During the course, students will:

  1. Identify various conjugated systems.
  2. Rationalize the increased stability of allylic systems.
  3. Predict the product distribution of addition reactions to allylic systems.
  4. Illustrate common reactions of conjugated systems.
  5. Differentiate between conjugated, isolated and cumulated dienes.
  6. Describe methods to prepare dienes.
  7. Predict the products of conjugate and direct addition of dienes.
  8. Predict the products of the Diels-Alder reaction.
  9. Explain the stereospecificity and regioselectivity of the Diels-Alder reaction.
  10. Rationalize pericyclic reactions using molecular orbital theory.

Outcome 2: Upon completion of this course, students will be able to demonstrate a working knowledge of the basic properties and reactions of arenes.

Objectives: During the course, students will:

  1. Describe aromatic stability.
  2. Use resonance to describe the structure and stability of aromatic compounds.
  3. Provide acceptable IUPAC names for mono- and polysubstituted derivatives of benzene.
  4. Compare the physical properties of aromatic and aliphatic hydrocarbons.
  5. Predict the product(s) following the reduction of a compound containing a benzene ring.
  6. Predict the product(s) following reactions that manipulate substituents on a benzene ring.
  7. Justify the stabilizing effect of benzene as a substituent.
  8. Use Hückel’s Rule to explain aromaticity.
  9. Explain the stability of annulenes.
  10. Justify the stability of aromatic ions and heterocyclic compounds.

Outcome 3: Upon completion of this course, students will be able to demonstrate a working knowledge of the electrophilic aromatic substitution (EAS) reactions of arenes.

Objectives: During the course, students will:

  1. Contrast the EAS reactions of arenes and eletrophilic addition reactions of alkenes.
  2. 3Predict the product(s) of representative EAS reactions of benzene.
  3. Rationalize the product(s) of EAS reactions of benzene mechanistically.
  4. Explain the regioselectivity of EAS reactions involving substituted benzenes.
  5. Account for the rates of EAS reactions of substituted benzenes using mechanisms and resonance.
  6. Predict the product(s) of EAS reactions of polysubstituted benzene rings.
  7. Predict the product(s) of EAS reactions involving heterocyclic and polycyclic aromatic compounds.

Outcome 4: Upon completion of this course, students will be able to demonstrate a working knowledge of organometallic compounds and their usefulness in carbon-carbon bond forming reactions.

Objectives: During the course, students will:

  1. Provide acceptable IUPAC names and structures to organometallic compounds.
  2. Describe reactions to prepare organometallic reagents.
  3. Compare the basic behavior of certain organometallic reagents.
  4. Predict the product(s) of reactions involving organometallic reagents.
  5. Use mechanisms to illustrate reactions involving organometallic reagents.
  6. Devise synthetic procedures using retrosynthetic analysis.
  7. Describe the preparation and reactions of carbenes and carbenoids.
  8. Recognize the stability of transition-metal organometallic compounds using the 18-electron rule.
  9. Explain the usefulness of transition-metal organometallic compounds in catalysis.

Outcome 5: Upon completion of this course, students will be able to demonstrate a working knowledge of the properties and reactivity of compounds containing alcohol, diol and thiol functionalities.

Objectives: During the course, students will:

  1. Illustrate natural sources and the properties of alcohols, diols and thiols.
  2. Explain common procedures for the preparation of alcohols and diols.
  3. Predict the product(s) of common reactions involving alcohols and diols.
  4. Provide acceptable IUPAC names and structures for thiols.
  5. Predict the product(s) of common reactions involving thiols.
  6. Use mechanisms to illustrate reactions involving alcohols, diols and thiols.

Outcome 6: Upon completion of this course, students will be able to demonstrate a working knowledge of the properties and reactivity of compounds containing ether, epoxide and sulfide functionalities.

Objectives: During the course, students will:

  1. Provide acceptable IUPAC names and structures for compounds containing ether, epoxide and sulfide functionalities.
  2. Describe the structure, bonding and physical properties of ethers, epoxides and sulfides.
  3. Illustrate the complexing ability of crown ethers and their usefulness as phase transfer reagents.
  4. Explain common procedures for the preparation of ethers, epoxides and sulfides.
  5. Predict the product(s) of common reactions involving ethers, epoxides and sulfides.
  6. Use mechanisms to illustrate reactions involving ethers, epoxides and sulfides.

Outcome 7: Upon completion of this course, students will be able to demonstrate a working knowledge of the properties and reactivity of compounds containing aldehyde and ketone functionalities.

Objectives: During the course, students will:

  1. Provide acceptable IUPAC names and structures for compounds containing aldehyde and ketone functionalities.
  2. Describe the structure, bonding and physical properties of compounds containing the carbonyl functional group.
  3. Explain common procedures for the preparation of aldehydes and ketones.
  4. Predict the product(s) of common nucleophilic addition reactions involving aldehydes and ketones.
  5. Use mechanisms to illustrate nucleophilic addition reactions involving aldehydes and ketones.
  6. Explain substitution effects on the stability and reaction rates of the carbonyl group.
  7. Describe the usefulness of acetals as protecting groups.
  8. Depict the synthesis of alkenes using the Wittig reaction.
  9. Explain the stereoselectivity of nucleophilic addition reactions of aldehydes and ketones.

Outcome 8: Upon completion of this course, students will be able to demonstrate a working knowledge of the properties and reactivity of compounds containing enol and enolate functionalities.

Objectives: During the course, students will:

  1. Describe the structure, bonding, physical and chemical properties of compounds containing the enol functional group.
  2. Predict the product(s) of reactions involving the ?-carbon atom and explain their formation mechanistically.
  3. Rationalize the equilibrium in keto-enol tautomerism.
  4. Predict the product(s) of acid and base catalyzed aldol addition and condensation reactions.
  5. Use mechanisms to illustrate acid and base catalyzed aldol addition and condensation reactions.
  6. Predict and explain the product(s) of direct and conjugate addition to ?,?-unsaturated carbonyl containing compounds.
  7. Use mechanisms to illustrate direct and conjugate addition to ?,?-unsaturated carbonyl containing compounds.

Outcome 9: Upon completion of this course, students will be able to demonstrate a working knowledge of the properties and reactivity of compounds containing carboxylic acid functionalities.

Objectives: During the course, students will:

  1. Provide acceptable IUPAC names and structures for compounds containing carboxylic acid functionalities.
  2. Describe the structure, bonding and physical properties of compounds containing the carboxylic acid functional group.
  3. Discuss substituent effects on the acidity of carboxylic acids.
  4. Rationalize the formation of micelles from carboxylate salts.
  5. Explain common procedures for the preparation of carboxylic acids.
  6. Predict the product(s) of common reactions involving carboxylic acids.
  7. Use mechanisms to illustrate common reactions involving carboxylic acids.

Outcome 10: Upon completion of this course, students will be able to demonstrate a working knowledge of the properties and reactivity of compounds containing amine functionalities.

Objectives: During the course, students will:

  1. Provide acceptable IUPAC names and structures for compounds containing amine functionalities.
  2. Distinguish between 1º, 2º and 3º amines.
  3. Describe the structure, bonding and physical properties of compounds containing the amine functional group.
  4. Discuss substituent effects on the basicity of amines.
  5. Rationalize the usefulness of tetralkylammonium salts as phase-transfer catalysts.
  6. Explain common procedures for the preparation of amines.
  7. Use mechanisms to illustrate the preparation of amines.
  8. Predict the product(s) of common reactions involving amines.
  9. Use mechanisms to illustrate common reactions involving amines.

Outcome 11: Upon completion of this course, students will be able to demonstrate a working knowledge of the properties and reactivity of compounds containing phenol functionalities.

Objectives: During the course, students will:

  1. Provide acceptable IUPAC names and structures for compounds containing phenol functionalities.
  2. Describe the structure, bonding and physical properties of compounds containing the phenol functional group.
  3. Discuss substituent effects on the acidity of phenol and its derivative.
  4. Predict the product(s) of common reactions involving compounds containing phenol functionalities.
  5. Use mechanisms to illustrate common reactions involving phenols.

COMMON DEGREE OUTCOMES (CDO)
• Communication: The graduate can communicate effectively for the intended purpose and audience.
• Critical Thinking: The graduate can make informed decisions after analyzing information or evidence related to the issue.
• Global Literacy: The graduate can analyze human behavior or experiences through cultural, social, political, or economic perspectives.
• Information Literacy: The graduate can responsibly use information gathered from a variety of formats in order to complete a task.
• Quantitative Reasoning: The graduate can apply quantitative methods or evidence to solve problems or make judgments.
• Scientific Literacy: The graduate can produce or interpret scientific information presented in a variety of formats.

CDO marked YES apply to this course:
Communication: YES
Critical Thinking: YES
Information Literacy: YES
Quantitative Reasoning: YES
Scientific Literacy: YES

COURSE CONTENT OUTLINE
Chemistry of Aromatic Compounds

  1. Rxns of Benzene and Substituted Benzenes
  2. Substituent Effects in Aryls, Synthesis of Aryls
  3. Structure, Properties, and Rxns of Aryl Halides
  4. Nomenclature, Structure, and Physical Properties of Amines
  5. Basicity and Preparation of Amines
  6. Rxns of Amines
  7. Structure, Properties, and Preparation of Phenols
  8. Rxns of Phenols

Organometallic Compounds

  1. Nomenclature and Preparation of Organometallic Compounds
  2. Use of Organometallic Reagents in Organic Synthesis

Chemistry of the Functional Groups

  1. Preparation of Alcohols, Diols, and Thiols
  2. Rxns of Alcohols, Diols, and Thiols
  3. The Chemistry of Ethers, Epoxides, Sulfides
  4. Nomenclature, Structure, and Preparation of Aldehydes and Ketones
  5. Rxns of Aldehydes and Ketones
  6. Organic Synthesis Involving Aldehydes and Ketones
  7. Properties and Structure of Enols and Enolates
  8. Rxns of Enols and Enolates
  9. Structure, Properties, and Preparation of Carboxylic Acids
  10. Rxns of Carboxylic Acids
  11. Structure, Properties, and Preparation of Carboxylic Acid Derivatives
  12. Rxns of Carboxylic Acid Derivatives
  13. The Claisen Condensation
  14. Other Rxns of Esters

Primary Faculty
Yang, Zhiqiang
Secondary Faculty

Associate Dean
Young, Randall
Dean
Pritchett, Marie



Official Course Syllabus - Macomb Community College, 14500 E 12 Mile Road, Warren, MI 48088



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