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Prof. Janina E. Kamińska Łódź University of Technology Faculty of Biotechnology and Food Sciences

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. 11:15-12:00, Fri. 14:15-15:00) Phone: 42 6313412

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Prof. Janina E. Kamińska Łódź University of Technology Faculty of Biotechnology and Food Sciences

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  1. 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. 11:15-12:00, Fri. 14:15-15:00) Phone: 42 6313412 E-mail: janina.kaminska@p.lodz.pl

  2. ORGANIC CHEMISTRY 1 sem. II. 2018/19 Lecture 30 h Tutorials 15 h Workload outside classroom 75 h ECTS credits: 4

  3. Final grade consist of: 13 June 2019: written tutorials test 50% 8 May 2019 and 26 June 2019 average of 2 written lecture tests 50%

  4. PERIODIC TABLE OF ELEMENTS

  5. Structures of some organic compounds Octane number = 100

  6. Structures of some organic compounds Vanilla flower Vanilla pods

  7. Structures of some organic compounds Antimalarial activity Cinchona tree

  8. Structures of some organic compounds Fragrance component Jasmine flowers

  9. Structures of some organic compounds Flavour and cooling effect Mentha species

  10. Structures of some organic compounds Sugar beet Sugar cane

  11. Structures of some organic compounds Artificial sweetener

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

  13. 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

  14. 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. • Mechanismsof organic reactions – parameters describing the reaction, energy profiles. General types of organic reactions. Writing balanced reaction equations. • Hydrocarbons: alkanes, cycloalkanes (radical halogenation); alkenes, alkynes (electrophilic addition to multiple bonds); arenes (electrophilic aromatic substitution).

  15. Lectures • 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 resonancespectroscopy (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 • Aldehydes and ketones – preparation and chemical reactions: nucleophilic addition to carbonyl group; -substitution reactions, carbonyl condensation reactions (aldol condensation). • Carboxylic acids and their derivatives (acyl chlorides, anhydrides, esters, amides, nitriles) – preparation and chemical behaviour (nucleophilic acyl substitution, -substitution reactions).

  16. 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.

  17. 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

  18. Textbooks Organic Chemistry with Biological Applications Organic Chemistry Fundamentals of Organic Chemistry

  19. ORGANIC CHEMISTRY 1 Lecture 1 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.

  20. Language of organic chemists

  21. Types of organic compounds HYDROCARBONFRAMEWORK HYDROCARBONFRAMEWORK FUNCTIONAL GROUP

  22. Drawing and naming of organic structures

  23. Rules for drawing skeletal structures • Carbon atoms are not shown. They assumed to be at each intersection of two lines (bonds) and at the end of each line. Occasionally, a carbon atom might be indicated for emphasis or clarity. • Hydrogen atoms bonded to carbon are not shown. Since carbon has always valence of 4, we mentally supply the correct number of hydrogen atoms to fill the valence of each carbon. • All atoms other than carbon and hydrogen (heteroatoms)are indicated.

  24. ALKANES (saturated hydrocarbons, aliphatic hydrocarbons) • Do not contain functional groups

  25. Functional groups. • With carbon-carbon multiple bonds Alkene Alkyne Arene (aromatic ring)

  26. Types of functional groups. • With carbon singly bonded to an electronegative atom Alkyl halide Alcohol Ether Amine Thiol (thioalcohol) Sulfide (thioether)

  27. Functional groups. • With carbon-oxygen double bond (carbonyl groups) Aldehyde Ketone Carboxylic acid Ester Amide Acid chloride

  28. Naming alkanes according to IUPAC rules Prefix—Parent—Suffix What are substituents?How many carbons?What family?

  29. Parent names of chain alkanes from C1to C20 C1 methane C2 ethane C3 propane C4 butane C5 pentane C6 hexane C7 heptane C8 octane C9 nonane C10 decane C11 undecane C12 dodecane C13 tridecane C14 tetradecane C15 pentadecane C16 hexadecane C17 heptadecane C18 octadecane C19 nonadecane C20 eicosane

  30. Naming alkanes according to IUPAC rules Step 1. Find the parent hydrocarbon – that means find the longest continuous carbon chain in the molecule: If 2 different chains are equal, choose the one with the larger number of branch points:

  31. Naming alkanes according to IUPAC rules Step 2. Number the atoms in the main chain beginning at the end nearer the first branch point: If there is branching an equal distance away from both ends, begin numbering at the end nearer the second branch point:

  32. Naming alkanes according to IUPAC rules Step 3. Identify and number the substituents: on C3, CH2CH3 (3-ethyl) on C2, CH3 (2-methyl) on C4, CH3 (4-methyl) on C4, CH3 (4-methyl) on C7, CH3 (7-methyl) on C4, CH2CH3 (4-ethyl) 3-ethyl-4,7-dimethylnonane4-ethyl-2,4-dimethylhexane Step 4. Write the name as a single word using hyphen to separate different prefixes, and commas to separate numbers. Prefixes should appear in alphabetical order.

  33. Naming alkanes according to IUPAC rules Step 5. When a substituent of the main chain has its own sub-branching. The name of complex substituent is formed applying the steps 1-4 just as if the substituent was a compound itself. Numbering in complex substituent starts alwaysat the point of attachment to the main chain.

  34. Common names of straight-chain and branched-chain alkyl substituents derived from C3 – C4 alkanes propane propyl isopropyl butane butyl sec-butyl

  35. Common names of straight-chain and branched-chain alkyl substituents derived from C4 – C5 alkanes isobutane isobutyl tert-butyl pentane pentyl

  36. Common names of straight-chain and branched-chain alkyl substituents derived from C5 alkanes isopentane isopentyl tert-pentyl neopentane neopentyl

  37. Naming cycloalkanes according to IUPAC rules Step 1. Use the cycloalkane name as the parent name When alkyl substituent contains more carbons than ring, use alkane as parent name.

  38. Naming cycloalkanes according to IUPAC rules Step 2. In substituted cycloalkanes number the atoms in the ring starting at the point of attachment so as to arrive at the lowest sum. When different substituents are present, they are numbered by alphabetical priority. correct wrong

  39. Nomenclature of alkenes according to IUPAC rules Alkenes are named according to a series of rules similar to those developed for alkanes, with the suffix –ene used instead of -ane to identify the family. Step 1. Find the parent hydrocarbon – that means find the longest carbon chain containing the double bond:

  40. Step 2. Number the atoms in the chain beginning at the end nearer the double bond. If the double bond is equidistant from the two ends, begin at the end nearer the first branch point. This rule assures that the double bond carbons receive the lowest possible numbers: 2-hexene 2-methyl-3-hexene Step 3. Write the full name numbering the substituents according to their position in the chain and listing them alphabetically. Indicate the position of the double bond by giving the number of the first alkene carbon. If more than one double bond is present indicate the position of each and use the suffixes -diene, -triene, -tetraene, and so on. 2-ethyl-1-pentene 2-methyl-1,3-butadiene

  41. Common names of unsaturated substituents accepted by IUPAC methylene ethylidene vinyl allyl ethenyl 2-propenyl

  42. Common and systematic names of some alkenes Systematic name Common name Ethene Ethylene Propene Propylene 2-Methylpropene Isobutylene 2-methyl-1,3-butadiene Isoprene

  43. Naming cycloalkenes according to IUPAC rules Cycloalkenes are named in a similar way, but because there is no chain end to begin from, we number the cycloalkene so that the double bond is between C1 and C2 and the first substituent has as low number as possible. 1-methylcyclohexene1,4-cyclohexadiene1,5-dimethylcyclopentene

  44. Nomenclature of alkynes according to IUPAC rules Alkynes follow the general rules of hydrocarbon nomenclature. The suffix –yne is used to denote an alkyne, and the position of the triple bond is indicated by its number in the chain. Numbering always begins at the chain end nearer the triple bond so that the triple bond receives as low a number as possible. 6-methyl-3-octyne

  45. Compounds with more than one triple bond are called diynes, triynes and so forth; compounds containing both double and triple bonds are called enynes (not ynenes). Numbering of an enyne chain always starts from the end nearer the first multiple bond, whether double or triple. When there is a choice in numbering, though, double bonds receive lower numbers than do triple bonds. 4-methyl-7-nonen-1-yne 1-hepten-6-yne 4-methylnon-7-en-1-yne hept-1-en-6-yne Names of alkynyl substituents: ethynyl 1-propynyl 1-butynyl

  46. Nomenclature of arenes BenzeneEthylbenzeneBromobenzene Disubstituted benzene derivatives: ortho-dibromobenzene meta-dibromobenzene para-dibromobenzene o-dibromobenzene m-dibromobenzene p-dibromobenzene 1,2-dibromobenzene 1,3-dibromobenzene1,4-dibromobenzene

  47. In tri- and more substituted benzenes the lowest possible numbers are used, and substituents are listed alphabetically 1,2-dibromo-4-methylbenzene1,3,5-trimethylbenzene1,4-dibromo-2,5-dimethylbenzene

  48. Aryl substituents Phenyl Benzyl C6H5-C6H5CH2- Ph- PhCH2- Bn

  49. Common names of some alkylbenzenes p-Cymene o-Xylene m-Xylene p-Xylene 1-isopropyl-4-methylbenzene 1,2-dimethylbenzene 1,3-dimethylbenzene 1,4-dimethylbenzene Cumene Mesitylene Styrene Isopropylbenzene 1,3,5-trimethylbenzene Vinylbenzene Ethenylbenzene

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