Builds on the concepts introduced in CHEM-241. Emphasizes acid-base chemistry, spectroscopy, and retrosynthetic analysis. Reaction mechanisms and physical properties of the following functional groups will be explored: carbonyl chemistry (aldehydes, ketones, and carboxylic acid derivatives); carboxylic acids; amines; carbohydrates; lipids; amino acids, proteins; and nucleotides. This course is designed to meet the requirements for science majors, pre-professional biology, pre-professional chemistry, as well as premedical, pre-dental, pre-pharmacy, veterinary, and chemical engineering students. Four hours of lecture per week without lab.
Goals, Topics, and Objectives
After completing Chemistry 242, students should:
- Be further acquainted with how organic chemistry impacts their lives on a daily basis.
- Be able to understand the basic mechanisms by which alkynes, ethers, aldehydes, ketones, carboxylic acids, carboxylic acid derivatives (acid halides, anhydrides, esters, amides, nitriles), other acid derivatives (sulfonamides, imides, phosphoric anhydrides, chromic anhydrides), amines, aromatics and other conjugated systems react.
- Be experienced in using critical thinking and the scientific method.
- Be more familiar with the work of organic chemists.
- Be prepared to enroll in higher level classes in chemistry
- Find greater appreciation for the complexity and beauty of the interrelationship between organic chemistry and biology.
Upon successful completion of this course, students should be able to (* indicates critical thinking objectives):
- Continued application of many concepts mastered in Chem 241 such as:
Drawing Organic Compounds Predicting acid-base equilibria by using pKa’s Chirality (“Handedness”) in chemical reactions and interactions of biochemicals
- Nomenclature; Structure; Physical and Chemical Properties of:
Alkanes and Cycloalkanes Alkenes Alkyl halides Alcohols Ethers
- Nomenclature; Structure; Physical and Chemical Properties of:
ethers, aldehydes, ketones, carboxylic acids, carboxylic acid derivatives (acid halides, anhydrides, esters, amides, nitriles), other acid derivatives (sulfonamides, imides, phosphoric anhydrides, chromic anhydrides), amines, aromatics and other conjugated systems
- Thorough study of the following reaction mechanisms:
- Williamson ether synthesis Acid-catalyzed addition of alcohols to alkenes (formation of ethers) Epoxidation of alkenes using RCO3H Halohydrin formation / Internal SN2 Acid-catalyzed opening of epoxides
- Nucleophilic opening of epoxides
- Grignard addition to aldehydes and ketones.
- Addition of terminal alkyne anions to aldehydes and ketones.
- Formation of a cyanohydrin.
- Phosphonium ylide formation / Wittig reaction.
- Acid catalyzed formation of hemiacetals and acetals.
- Reactions of 1,3-dithiane anions with electrophiles.
- Imine formation from aldehydes and ketones.
- Keto/Enol tautomerization. (i) Acid-catalyzed. (ii) Base-catalyzed.
- Acid-Catalyzed a-halogenation of a ketone.
- Base-Catalyzed a-halogenation of a ketone (Haloform reaction).
- NaBH4 reduction of aldehydes and ketones.
- Wolff-Kishner Reduction Fischer esterification.
- Formation of methyl esters using diazomethane (CH2N2).
- Reaction of carboxylic acids with SOCl2 Decarboxylation of b-carbonyl containing carboxylic acids.
- Nucleophilic acyl substitution.
- Acid-catalyzed hydrolysis of carboxylic acid derivatives.
- Base-catalyzed hydrolysis of carboxylic acid derivatives.
- Reactions of Carboxylic acid derivatives with alcohols.
- Reaction of acid halides with amines to give amides.
- Reactions of esters with Grignard reagents and organolithium reagents.
- Reduction of Carboxylic acid derivatives.
- The Hofmann rearrangement of primary amides.
- Base-catalyzed aldol reactions/Base-catalyzed dehydrations.
- Acid-catalyzed aldol reactions/Acid-catalyzed dehydrations.
- Claisen condensation.
- Dieckmann condensation.
- Formation of Isopentenyl pyrophosphate (precursor to cholesterol/hormones/terpenes).
- Alkylation/Acylation of enamines.
- Acetoacetic/Malonic ester syntheses.
- Michael reaction: Conjugate addition (1,4) of stabilized enolate anions.
- Kolbe synthesis: carboxylation of phenol towards the pharmaceutical synthesis of aspirin.
- Benzylic Resonance Electrophilic aromatic substitution: Chlorination Formation of the nitronium ion/Sulfonation.
- Friedel-Crafts alkylation/Friedel-Crafts acylation and generation of acyl cation.
- Other Friedel-Crafts Reactions Formation of the nitrosyl cation (NO+).
- Reactions of secondary amines with the nitrosyl cation to give N-nitrosamines.
- Reactions of primary amines with the nitrosyl cation to give diazonium ions.
- The Tiffeneau-Demjanov rearrangement.
- The Hofmann Elimination.
- The Cope elimination 1,2 and 1,4-addition to a conjugated diene.
- The Diels-Alder reaction.
- The Claisen rearrangement.
- The Cope Rearrangement Radical polymerization of alkenes (time permitting).
- Anionic polymerization of alkenes and conjugated alkenes (time permitting).
- Cationic polymerization of alkenes and conjugated alkenes (time permitting).
- Acid-catalyzed formation of glycosides (review acetal formation).
- Formation of dimethylallyl cation/Reaction to geranyl pyrophosphate (time permitting).
- From Squalene to Lanosterol (time permitting).
- Oxidation of an alcohol by NAD+(time permitting).
- Unsaturated fatty acids from saturated fatty acids using FAD oxidation (time permitting).
- Claisen reactions in biochemistry.
- Reverse aldol reactions in biochemistry.
- The reactions in Glycolysis.
- The reactions in the citric acid cycle.
- The reactions in the biosynthesis of: fatty acids, terpenes, and steroids.
Students who successfully complete the assignments of this course should be able to:
- Demonstrate various levels of proficiency with predicting the mechanisms of reactions of various classes of organic molecules including, but not limited to ethers, aldehydes, ketones, carboxylic acids, carboxylic acid derivatives (acid halides, anhydrides, esters, amides, nitriles), other acid derivatives (sulfonamides, imides, phosphoric anhydrides and esters, chromic anhydrides), amines, aromatics and other conjugated systems.
- Demonstrate the use of critical thinking skills in the analysis of chemical reactions.*
- Recognize and give examples of the importance of searching for patterns when one is studying the sciences and carrying out investigations and/or experiments.
- Name complicated organic and biochemical molecules.
- Devise a synthesis for relatively elaborate organic compounds (using retrosynthetic analysis).*
- Predict the physical properties of molecules based on an understanding of functional groups.
- Predict reactions between molecules base on an understanding of functional groups and bonding.
- Describe how chemical reactions mediate biological processes.
- Demonstrate competence with identification of functional groups and organic reactions of biomolecules.
- Demonstrate proficiency with course management software such as Blackboard or UCompass.
Assessment and Requirements
Student assessment is built into the course objectives. Objectives were written using wording which allows their achievement to be measured. Students will be assessed on:
- In Class Questions, both verbal and written.
- Pre Class Questions, both written and electronic.
- On-line Web Based Learning (OWL) provided by text publisher which allows students to complete homework type problems, receive immediate feedback, and allows them to redo the material until they get it right.
- Lecture examinations consisting of objective questions and short essays.
- Professional behavior and attitude.
Text will be a book designed for use by students entering into health related careers such as pharmacy, dentistry, medicine, chiropractic, and veterinary. One such book being W. H. Brown, C. S. Foote Organic Chemistry, 4th Ed. New York: Saunders College Publishing, 2005.