CHM4251 ORGANIC CHEMISTRY II with Lab
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 with Lab. 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.
[KRSN: CHM2020]
Course Classification: Lecture/Lab (3 hour lecture / 2 hour lab)
Prerequisites:
CHM 4250 Organic Chemistry I with Lab and basic computer skills
Co-requisites:
NONE
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. This course is designed to help the student to prepare for professional applications in a science such as chemistry or biology, and medicine and other pre-professional fields.
Core Outcomes:
The learning outcomes and competencies detailed in this course meet, or exceed the learning outcomes and competencies specified by the Kansas Core Outcomes Project for this course, as sanctioned by the Kansas Board of Regents.
Learner Outcomes:
Upon completion of this course, the student will be able to:
• Characterize organic molecules using spectroscopic techniques; mass spec, IR, and NMR.
• Demonstrate an understanding of the fundamentals of bonding and reactivity in conjugated and aromatic systems.
• Demonstrate the ability to apply IUPAC nomenclature rules, including stereogenic centers, and identify functional groups in molecules related to Organic II topics.
• Predict products and demonstrate an understanding of the mechanisms of reactions involving ethers, epoxides, thiols, aldehydes, ketones, carboxylic acids and their derivatives, and amines.
• Demonstrate an understanding of formation and reactivity of enolates, including thermodynamic versus kinetic control.
• Demonstrate an ability to prepare, separate, purify, and characterize organic compounds, including using spectroscopic data.
• Effectively communicate procedures, results, experimental data, sources of experimental error, and conclusions drawn from data.
• Demonstrate awareness of potential safety hazards and conduct organic experiments safely and responsibly, including proper hazardous waste disposal.
Unit Outcomes for Criterion Based Evaluation:
The following outline defines the minimum core content not including the final examination period.
UNIT 1: SPECTROSCOPY
Outcomes: Upon completion of this unit, the student will discuss and apply spectroscopic techniques to determine structural aspects and identify organic molecules.
The student will be able to:
- Describe the techniques and apply UV-Visible spectroscopy and infrared spectroscopy to identify structural features of organic molecules.
- Describe the techniques and apply Nuclear Magnetic Resonance (NMR) spectroscopy to identify structures of organic molecules.
UNIT 2: CONJUGATED SYSTEMS
Outcomes: Upon completion of this unit, the student will be able to discuss and apply Diels-Alder and addition reactions of conjugated systems to achieve the synthesis of a target molecule.
The student will be able to:
- Identify types of conjugated systems and apply IUPAC nomenclature rules.
- Illustrate the mechanism for Diels-Alder reactions.
- Describe the stereospecific, bicyclic, and asymmetrical products of Diels Alder reactions.
- Discuss the relationship between structures of conjugated systems and wavelength in ultraviolet spectroscopy.
UNIT 3: AROMATIC COMPOUNDS AND REACTIONS
Outcomes: Upon completion of this unit, the student will be able to identify and discuss properties of aromatic structures and predict products of aromatic reactions.
The student will be able to:
- Evaluate aromaticity of a structure based on structural and conceptual perspectives.
- Apply IUPAC nomenclature rules to aromatic compounds.
- Describe electrophilic reactions and mechanisms of aromatic compounds.
- Distinguish between activating and deactivating substituents and ortho-para and meta directing substituents in electrophilic aromatic substitution reactions.
- Design a Friedel-Crafts Alkylation or Acylation synthesis for a target compound.
UNIT 4: ORGANOMETALLIC REACTIONS
Outcomes: Upon completion of this unit, the student will be able to describe organometallic reactions and utilize these reactions to complete a desired synthesis.
The student will be able to:
- Discuss the mechanism and predict products of reactions that utilize organolithium and organomagnesium (Grignard) reagents.
- Discuss the mechanism and predict products of reactions that utilize organocuprate (Gilman) reagents.
- Discuss the mechanism and predict products of reactions that utilize the organozinc (Simmons-Smith) reagent.
- Discuss the mechanism and predict the products of reactions that utilize palladium catalyzed cross coupling reagents such as the Suzuki and Heck reactions.
UNIT 5: OXIDIZING AND REDUCING AGENTS
Outcomes: Upon completion of this unit the student will be able to describe the properties of oxidizing and reducing agents and select the appropriate reagent to complete a desired transformation of a functional group.
The student will be able to:
- Discuss common reducing agents for carbonyl compounds such as sodium borohydride and lithium aluminum hydride, and select an appropriate reducing agent to complete the desired reduction of a carbonyl compound.
- Discuss common oxidizing agents such as chromium VI compounds, and select an appropriate oxidizing agent for the conversion of an alcohol to a carbonyl compound.
UNIT 6: ALDEHYDES AND KETONES
Outcomes: Upon completion of this unit, the student will be able to discuss the structures and reactivity of aldehydes and ketones.
The student will be able to:
- Describe the reactions of aldehydes and ketones with nucleophiles at the carbonyl group.
- Illustrate and discuss the mechanisms of the reactions that produce acetals, cyanohydrins, imines, enamines, and the Wittig reaction.
UNIT 7: CARBOXYLIC ACIDS AND DERIVATIVES
Outcomes: Upon completion of this unit, the student will be able to describe the properties, apply nomenclature, and discuss reactivity of carboxylic acids and derivatives.
The student will be able to:
- List the structures and relative reactivity of carboxylic acid derivatives.
- Illustrate the mechanism for the synthesis of carboxylic acids and derivatives.
- Propose a synthetic reaction sequence for acid chlorides, esters, amides, and hydrolysis products of carboxylic acid derivatives.
- Describe factors that affect the acidity of carboxylic acids.
UNIT 8: ENOLS AND ENOLATES
Outcomes: Upon completion of this unit, the student will be able to describe and apply alkylation, addition, and condensation reactions of enols and enolates.
The student will be able to:
- Discuss the structure, nomenclature and reactivity of nucleophilic enols.
- Differentiate between thermodynamic and kinetic regioselectivity of enolates.
- Describe the reactions of enols and enolates with carbonyls and conjugated unsaturated molecules.
UNIT 9: AMINES
Outcomes: Upon completion of this unit, the student will be able to discuss and apply the basic character and reactivity of amines.
The student will be able to:
- Describe the structural basis for the basicity of amines.
- Identify structures, apply nomenclature, and describe the reactivity of amines.
- Illustrate the synthesis of an amine.
- Discuss nitrosation, reduction, and re-arrangements of amines.
- Describe the Hofmann elimination of quaternary amines.
UNIT 10: CARBOHYDRATES
Outcomes: Upon completion of this unit, the student will be able to discuss and analyze the chemistry and structure of carbohydrates.
The student will be able to:
- Illustrate the structure and nomenclature of carbohydrates by drawing and naming.
- Discuss the stereochemical configuration and biological importance of carbohydrates.
- Differentiate relative and absolute configurations of carbohydrates and illustrate chirality 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.
Projects Required:
Laboratory notebook.
Textbook:
Contact the Bookstore for current textbook information.
Materials/Equipment:
Refer to course syllabus.
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.
DISCLAIMER: THIS INFORMATION IS SUBJECT TO CHANGE. FOR THE OFFICIAL COURSE PROCEDURE CONTACT ACADEMIC AFFAIRS.
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