ORGANIC CHEMISTRY 1 Prof. Janina E. Kamińska Łódź University of Technology Faculty of Biotechnology and Food Sciences Institute of General Food Chemistry ul. Stefanowskiego 4/10 Room no 209 (Consultation hours: Wed. 14:15-15:00, Fri. 14:15-15:00) Phone: 42 6313412 E-mail: janina.kaminska@p.lodz.pl

Tutorials 15 h Lecture 30 h Tutorials 15 h Tutorials 15 h Lecture 30 h ORGANIC CHEMISTRY 1 sem. II. 2017/18 Tutorials 15 h Lecture 30 h ORGANIC CHEMISTRY 2 sem. III. 2018/19 Tutorials 15 h Tutorials 15 h Lecture 30 h Laboratory 45 h

ORGANIC CHEMISTRY 1 sem. II. 2017/18 Lecture 30 h Tutorials 15 h Workload outside classroom 75 h ECTS credits: 4

Final grade consist of: 14 June 2018: written tutorials test 50% 18 April 2018 and 20 June 2018 average of 2 written lecture tests 50%

PERIODIC TABLE OF ELEMENTS

Structures of some organic compounds Octane number = 100

Structures of some organic compounds Vanilla flower Vanilla pods

Structures of some organic compounds Antimalarial activity Cinchona tree

Structures of some organic compounds Fragrance component Jasmine flowers

Structures of some organic compounds Flavour and cooling effect Mentha species

Structures of some organic compounds Sugar beet Sugar cane

Structures of some organic compounds Artificial sweetener

Structures of some organic compounds Synthetic compound increasing man’s sexual potency

The main components of organic chemistry as a discipline are these: 1. STRUCTURE DETERMINATION – how to find out the structures of new compounds even if they are available only in invisibly small amounts 2. THEORETICAL ORGANIC CHEMISTRY – how to understand those structures in terms of atoms and the electrons that bind them together 3. REACTIONS MECHANISMS – how to find out how these molecules react with each other and how to predict their reactions 4. SYNTHESIS – how to design new molecules and then make them in the laboratory 5. BIOLOGICAL CHEMISTRY – how to find out what Nature does and how the structures of biologically active molecules are related to what they do

Lectures Structure and bonding in organic compounds. Covalent and ionic bonds. Hybridization of carbon (sp3, sp2, sp). Basic conceptions and definitions – acidity, basicity, polarity, polarizability, nucleophilicity, electrophilicity. Structure and molecular properties. Isomerism of organic compounds: constitutional and stereoisomerism (cis-trans isomers, chirality of carbon, optical rotation, absolute configuration of chiral carbon, racemate, enantiomers, diastereomers, meso compounds). Writing and naming of stereoisomers. Mechanisms of organic reactions – parameters describing the reaction, energy profiles. General types of organic reactions. Writing balanced reaction equations.

Lectures Hydrocarbons: alkanes, cycloalkanes (radical halogenation); alkenes, alkynes (electrophilic addition to multiple bonds); arenes (electrophilic aromatic substitution). Methods of isolation and purification of organic compounds (crystallization, distillation, chromatography). Structure determination by spectroscopic methods: general principles of mass spectrometry (MS), infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR), ultraviolet spectroscopy (UV). Alkyl halides – nucleophilic substitution and elimination (SN1, SN2, E1, E2 mechanisms) Alcohols, phenols – preparation and chemical reactivity. Ethers and epoxides - preparation and chemical reactivity. Overview of carbonyl group chemistry

Tutorials Different manners of writing and drawing structural formulas of organic molecules. Systematic (IUPAC) and common names of hydrocarbons. Systematic (IUPAC) and common names of compounds with single functional group. Isomerism of organic compounds. a) Constitutional isomerism b) Stereoisomerism. Writing and drawing stereoisomers on the plane. Cis-trans isomers of alkenes and cycloalkanes. Chirality of organic molecules – enantiomers. Absolute and relative configuration of chiral centre. Equation of chemical reaction – its meaning and application. Material balance in chemical equation. Classifying of organic reactions into general categories: addition, elimination, substitution, rearrangement. Chemical reactivity of hydrocarbons: alkanes, alkenes, alkynes, arenes.

Textbooks In English: John McMurry, “Organic Chemistry”, 8th ed. Brooks/Cole Publishing Co., Pacific Grove, California (or earlier editions) K. P. C. Vollhardt, N. E. Schore, “Organic Chemistry, Structure and Function”, 3rd ed. W. H. Freeman and Co., New York 1999 F. A. Bettelheim, J. March, “General, Organic and Biochemistry”, 5th ed. Harcourt Brace College Publishers 1998 J. Clayden, N. Greeves, S. Warren, P. Wothers, “Organic Chemistry”, Oxford University Press 2000 In Polish: John McMurry, “Chemia organiczna”, t1/2, translation from 4th ed., PWN Warszawa 2000 (or later editions) H. Hart, L. E. Craine, D. J. Hart, “Chemia organiczna. Krótki kurs”, Wyd. I, PZWL Warszawa 1999

Textbooks Organic Chemistry with Biological Applications Fundamentals of Organic Chemistry