Organic Chemistry 2

Code

Course teacher

Associate teachers

Status of the course

Course objectives

Acquisition of basic knowledge about chemistry of carbonyl compounds, carboxylic acid and derivatives, heterocycles and carbohydrates.
This course is basis for understanding other courses, such as Natural products, Organic synthesis, Organic analysis, Biochemistry.

Course enrolment requirements and entry competences required for the course

Enrolled in or passed the course Experimental Organic Chemistry II

Learning outcomes expected at the level of the course (4 to 10 learning outcomes)

After passing the exam students will be able to:
- recognize and give the IUPAC name to carbonyl compounds, carboxylic acids and derivatives, heterocycles and carbohydrates, and draw the corresponding structural formula based on systematic name (apply basic rules of organic compounds nomenclature)
- connect organic compounds molecular structure with their physico - chemical
properties and reactivity
- differentiate, describe and compare reaction mechanisms of nucleophilic addition and nucleophilic substitution at carbonyl group
- specify the most important reactions of carbonyl and carboxylic compounds
- describe heterocycles and carbohydrates reaction mechanisms, specify the most important reactions of these compounds
- solving problems regarding carbonyl compounds, carboxylic acid and derivatives, heterocycles and carbohydrates

Course content broken down in detail by weekly class schedule (syllabus)

Lectures (2 hours weekly):
1st week: Introduction to course (course content, students responsibilities, terms and conditions for passing exam). Nucleophilic aromatic substitution. Addition-elimination mechanism. Elimination-addition mechanism. Aryl cation mechanism.
2nd week: Polycyclic aromatic compounds - sources. Polycyclic aromatic compounds reactions. Nucleophilic addition to carbonyl group - introduction. Cyanide as a nucleophile (cyanohydrin formation).
3th week: Oxygen and sulphur as nucleophiles. Addition of alcohols (hemiacetals and acetals formation). Addition of water (hydrates formation). Addition of thiols (hemithioacetals and thioacetals formation). Hydride as a nucleophile - reduction. Reduction by complex metal hydrides. Cannizzaro reaction -disproportionation.
4th week: Carbon as a nucleophile - organometallic compounds. Organometallic reagents synthesis. Grignard reaction. Syntheses using Grignard reagents.
5th week: Nitrogen as a nucleophile. Imines. Enamines. Nucleophilic addition to carbonyl related compounds. Nucleophilic addition to imines. Nucleophilic addition to enamines. Nucleophilic addition to nitriles.
6th week: Nucleophilic acyl substitution - introduction. Carboxylic acids and derivatives reactivity. Oxygen and sulfur as nucleophiles. Substitution with alcohols - esterification. Lactonization. Transesterification. Substitution with water - hydrolysis.
7th week: Substitution with thiols. Nitrogen as a nucleophile. Acyl halides and anhydrides. Acyl halide synthesis. Anhydride synthesis.
8th week: Hydride as a nucleophile - reduction. Carbon as a nucleophile - organometallic reagents. Reactions with esters. Reactions with acyl halides. Reactions with carboxylic acids.
9th week: Nucleophilic substitution on derivatives of sulfuric and phosphoric acid. Nucleophilic reactions involving enolate anions. Enols and enolate anions. Enolization (keto-enol tautomerism). The aldol reaction.
10th week: Mixed aldol reaction. Dehydration of aldol products. Ester condensation – Claisen condensation.
11th week: Mixed Claisen condensation. -dicarbonyl compounds splitting. Reverse Claisen reaction. Decarboxylation.
12th week: Alkylation of enolate anions. Active methylene compounds.
Conjugate addition reactions. Electrophilic conjugate addition - conjugated dienes.
13th week: Nucleophilic conjugate addition - ,-unsaturated carbonyl compounds. Michael reaction. Diels-Alder cycloaddition.
14th week: Carbohydrates – definition and classification. Cyclic forms of monosaccharides and their representation. Reactions of monosaccharides. Oxidation. Reduction. Monosaccharides in aqueous solution (mutarotation). Monosaccharides in alkaline or acidic solution.
15th week: Glycosides. Typical disaccharides and polysaccharides.
Heterocyclic compounds (five-membered and six-membered heterocycles). Structures and stability of aromatic heterocycles. Electrophilic and nucleophilic aromatic substitution reactions.
Seminars (1 hour weekly):
Solving problems in organic chemistry.

Format of instruction:

Student responsibilities

Students are required to attend lectures and seminars in the amount of at least 80% of the times scheduled and complete all laboratory exercises (100% attendance). Active participation in teaching process will be also evaluated in the final score.

Optional literature (at the time of submission of study programme proposal)

T. W. Solomons & C. B. Fryhle, Organic Chemistry, John Wiley & Sons, Inc., New York, 2004.
J. Clayden, N. Greeves, S. Warren, P. Wothers, Organic Chemistry, Oxford University Press, Oxford, 2005.

Quality assurance methods that ensure the acquisition of exit competences

Monitoring of quality assurance will be performed at three levels:
(1) University Level, conducting surveys of students on teaching quality;
(2) Faculty Level, by Quality Control Committee;
(3) Lecturer’s Level, monitoring and accepting suggestions of students and colleagues

Other (as the proposer wishes to add)