Feb 19, 2020  
2019 - 2020 Cowley College Academic Catalog 
    
2019 - 2020 Cowley College Academic Catalog

CHM4251 ORGANIC CHEMISTRY II COURSE PROCEDURE


CHM4251 ORGANIC CHEMISTRY II

5 Credit Hours

Student Level:

This course is open to students on the college level in the sophomore year.

Catalog Description:

CHM4251 - Organic Chemistry II (N) (5 hrs.) 

A continuation of CHM5250 Organic Chemistry I. This course is an introduction to NMR, IR, and mass spectroscopy, synthetic organic chemistry, and compounds of biological interest. This course is for science and pre-professional students and includes laboratory experimentation.

Course Classification: Lecture/Lab

Prerequisite: 

CHM4250 Organic Chemistry I and basic computer skills.

Controlling Purpose: 

This is the second semester of a two-semester course in organic chemistry.  This material will allow the student to become functional in the mechanistic rational for the behavior of organic reactants and important synthetic reaction mechanisms.  The student will also be able to read and interpret IR, MNR, and mass spectrometer data.

Learner Outcomes:

Upon completion of the course, the student will have the conceptual tools to understand and apply the relationship between the structures of organic compounds and their properties.

Unit Outcomes for Criterion Based Evaluation:

The following defines the minimum core content not including the final examination period. Instructors may add other content as time allows.

UNIT 1: Carboxylic Acids and Their Derivatives

Outcomes: Upon completion of this unit, the student will understand the properties, nomenclature and reactivity of carboxylic acids and their derivatives.

  • List the structure and reactive sites of carboxylic acids and their derivatives.
  • Demonstrate the mechanism for the synthesis of carboxylic acids.
  • Propose a synthetic reaction sequence for the acid chlorides, esters, and hydrolysis products of carboxylic acids.
  • Describe the rational for the acidity of carboxylic acids.

UNIT 2: Synthetic Transformations of Carboxylates

Outcomes: Upon completion of this unit, the student will have gained an understanding of synthetic transformations of carboxylates.

  • Describe the synthesis of a Grignard reagent.
  • Illustrate a synthesis of a carboxylic derivative with an organometallic reagent.

UNIT 3: Enols and Enolates

Outcomes: Upon completion of this unit, the student will have gained an understanding of Alkylation and Condensation of Enols and Enolates.  

  • Relate the structure, nomenclature and reactivity of nucleophilic enols.
  • Differentiate between thermodynamic and kinetic regioselectivity of enoltes.
  • Describe the reactions of enols and enolates with carbonyls and carbanions.

UNIT 4: Diels-Alder and Polyenes

Outcomes: Upon completion of this unit, the student will have gained an understanding of Diels-Alder and Addition reactions of Polyenes.

  • Relate the structural details and nomenclature of polyenes.
  • Illustrate the reaction pathways for Diels-Alder reactions.
  • Describe the stereospecific, bicyclic, and unsymmetrical products of Diels Alder reactions.
  • Demonstrate relationship between structure and wavelength in ultraviolet spectroscopy.

UNIT 5:  Unsaturated Carbonyl and Carbanion

Outcomes: Upon completion of this unit, the student will have gained an understanding of the structure and reactivity of unsaturated carbonyl and carbanions species of Ylides.

  • Describe the reactions of electrophilic unsaturated carbonyls with nucleophiles.
  • Diagram a Michael reaction and a Wittig reaction of a carbonyl compound.

UNIT 6:  Aromatic Electrophilic Reactions

Outcomes: Upon completion of this unit, the student will have gained an understanding of the structure and reactivity of aromatic compounds.

  • Demonstrate knowledge of aromaticity from structural and theoretical considerations.
  • Relate nomenclature for aromatic compounds.
  • Describe electrophilic reactions and sulfonation of aromatics.
  • Distinguish between activators, deactivators and director substituents of benzene rings.
  • Postulate a Friedel-Crafts Alkylation and Acylation synthesis.

UNIT 7:  Radical Reactions of Alkanes

Outcomes: Upon completion of this unit, the student will have gained an understanding of free radical reactions of alkanes.

  • Describe halogenation of alkane radicals and detail a mechanistic pathway.
  • Illustrate Anti-Markovnikov additions with bromides.
  • Describe the oxidation and auto-oxidation of free radicals and phenols in biochemical species.

UNIT 8:  Amines

Outcomes: Upon completion of this unit, the student will have gained an understanding of the chemistry of Amines.

  • Describe the structural basicity of amines.
  • Illustrate the structure, nomenclature, and reactivity of amine species.
  • Describe the synthesis of an amine.
  • Discuss the nitrosation, reduction, and re-arrangements of amines.
  • Describe the Hofmann elimination of quaternary amines.

UNIT 9: Aromatic Systems

Outcomes: Upon completion of this unit, the student will have gained an understanding of the synthetic transformations of aromatic systems by nucleophilic substitution, oxidation, and the Sandmeyer reaction.

  • Discuss the mechanism and transformation of aryl compounds by the Sandmeyer reaction.
  • Describe the mechanism and rational for nucleophilic aromatic substitution.
  • Describe the synthesis of azo dyes and indicators.
  • Discuss the spectroscopic analysis of aromatic species by ultra-violet spectra.

UNIT 10: Heterocyclic Compounds and Reactivity

Outcomes: Upon completion of this unit, the student will have gained an understanding of Heterocyclic compounds and reactivity.

  • Express knowledge of nomenclature and structure of heterocycles by identification of species by IUPAC name.
  • Discuss the mechanism for the reactions of heterocycles as acids and bases.
  • Describe the synthesis of heterocycles with nucleophilic carbonyl compounds.
  • Discuss the mechanism of importance for biologically active heterocycles.

UNIT 11:  Carbohydrates

Outcomes: Upon completion of this unit, the student will have gained an understanding of the chemistry and structure of carbohydrates.

  • Illustrate the structure and nomenclature of carbohydrates by drawing and naming.
  • Discuss the stereo chemical configuration and biological importance of stereo chemical carbohydrates.
  • Differentiate relative and absolute configurations of carbohydrates and chiralty with Fischer projections.
  • Discuss the reactions of monosaccharides as carbonyl compounds.
  • Discuss the synthetic transformation of monosaccharides and the characteristics of polysaccharides, and other naturally occurring sugars.

UNIT 12:  Electrocyclic, Cycloaddition, and Carbene Concerted Reactions

Outcomes: Upon completion of this unit, the student will have gained an understanding of electrocyclic, cycloaddition, and carbene concerted reactions.

  • Discuss the evolution of the concerted reaction theory.
  • Describe photochemical dimerization and the MP picture of the Diels-Alder reaction.
  • Illustrate electrocyclic reactions of cyclobutenes and cyclohexatrienes.
  • Discuss the mechanism of the Cope re-arrangement.
  • Discuss the Claisen re-arrangement.

Projects Required:    

None

Textbook:   

Contact the Bookstore for current textbook information.

References:  

MSDS Catalogue, CRC Handbook of Chemistry and Physics, the Merck Index

Materials/Equipment:  

Organic lab glassware, Gas Chromatograph, PC computers, Fume Hood, Organic molecular model kits, Meltemps.

Attendance Policy:

Students should adhere to the attendance policy outlined by the instructor in the course syllabus.

Grading Policy:

The grading policy will be outlined by the instructor in the course syllabus.

Maximum class size:

Based on classroom occupancy

Course Timeframe:  

The U.S. Department of Education, Higher Learning Commission and the Kansas Board of Regents define credit hour and have specific regulations that the college must follow when developing, teaching and assessing the educational aspects of the college. A credit hour is an amount of work represented in intended learning outcomes and verified by evidence of student achievement that is an institutionally established equivalency that reasonably approximates not less than one hour of classroom or direct faculty instruction and a minimum of two hours of out-of-class student work for approximately fifteen weeks for one semester hour of credit or an equivalent amount of work over a different amount of time. The number of semester hours of credit allowed for each distance education or blended hybrid courses shall be assigned by the college based on the amount of time needed to achieve the same course outcomes in a purely face-to-face format.

Refer to the following policies:

402.00 Academic Code of Conduct

263.00 Student Appeal of Course Grades

403.00 Student Code of Conduct

Disability Services Program:  

Cowley College, in recognition of state and federal laws, will accommodate a student with a documented disability.  If a student has a disability, which may impact work in this class which requires accommodations, contact the Disability Services Coordinator.