1 כימיה אורגנית לתלמידי רפואה, מדעי הרפואה, ורפואת שיניים ד"ר עידית תשובה המחלקה לכימיה אי אורגנית בניין לוס-אנג'לס, חדר האוניברסיטה העברית

2 כימיה אורגנית לתלמידי רפואה, מדעי הרפואה ורפואת שיניים תוכן הקורס Organic Chemistry, 4 th Edition, Paula Yurkanis Bruice Organic Chemistry, 5 th Edition, Paula Yurkanis Bruice OR אתר הקורס:

3 ChaptersTopic *** 1 *** *** Electronic structure and bonding acids and bases; Mandatory self reading *** 22An introduction to organic compounds; nomenclature, properties, structures 3-4 Alkenes; structure, nomenclature, reactivity 55Stereochemistry 66Alkynes 7-87Delocalization and resonance, Dienes 911Reactions of alkanes Substitutions and eliminations; alkyl halides, alcohols, ethers, epoxides, Griniard reactions 1514Aromaticity 1615Reactions of aromatic compounds Carbonyl compounds 2019Oxidation-reduction 22,23,26,2721,22,26,27 Bioorganic compounds; carbohydrates, proteins, lipids, nucleic acids -*** 25 ****** The Chemistry of metabolism; Highly recommended self reading *** כימיה אורגנית לתלמידי רפואה, מדעי הרפואה ורפואת שיניים סילבוס 4th5th

4 Organic Chemistry, 4 th Edition, Paula Yurkanis Bruice Chapter 2 Pg An Introduction to Organic compounds Nomenclature, Physical Properties, and Representation of Structure Irene Lee Case Western Reserve University Cleveland, OH ©2004, Prentice Hall קריאה מלווה מחייבת Chapter 2 Pg An Introduction to Organic compounds Nomenclature, Physical Properties, and Representation of Structure Organic Chemistry, 5 th Edition, Paula Yurkanis Bruice

5 Organic compounds are compounds containing carbon Carbon neither readily gives up nor readily accepts electrons Carbon shares electrons with other carbon atoms as well as with several different kinds of atoms Organic Chemistry

6 Alkanes are hydrogen carbons containing only single bonds General formula: C n H 2n+2 Alkanes (אלקאנים)

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8 Constitutional isomers have the same molecular formula, but their atoms are linked differently Isomers

9 Nomenclature of Alkyl Substituents R – OH R – NH 2 R – X An alcoholAn amineAn alkyl halide X = F, Cl, Br, I

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11 A compound can have more than one name, but a name must specify only one compound A C 7 H 16 compound can be any one of the following:

12 Different Kinds of Carbons and Hydrogens

13 Nomenclature of Alkanes 1. Determine the number of carbons in the parent hydrocarbon 2. Number the chain so that the substituent gets the lowest possible number

14 3. Number the substituents to yield the lowest possible number in the number of the compound (substituents are listed in alphabetical order) 4. Assign the lowest possible numbers to all of the substituents

15 5. When both directions lead to the same lowest number for one of the substituents, the direction is chosen that gives the lowest possible number to one of the remaining substituents 6. If the same number is obtained in both directions, the first group receives the lowest number

16 7. In the case of two hydrocarbon chains with the same number of carbons, choose the one with the most substituents 8. Certain common nomenclatures are used in the IUPAC system

17 Nomenclature of Cycloalkanes 1. No number is needed for a single substituent on a ring 2. Name the two substituents in alphabetical order General formula: C n H 2n

18 3. If there are more than two substituents,

19 Nomenclature of Alkyl Halides In the IUPAC system, alkyl halides are named as substituted alkanes

20 Different Kinds of Alkyl Halides

21 Nomenclature of Ethers As substituents:

22 Nomenclature of Alcohols In an alcohol, the OH is a functional group A functional group is the center of reactivity in a molecule 1. Determine the parent hydrocarbon containing the functional group, where the functional group received the lowest number

23 2. The functional group suffix should get the lowest number 3. When the functional group suffix is the same, the substituent gets the lowest number

24 4. If there is more than one substituent, the substituents are cited in alphabetical order

25 Nomenclature of Amines The substituents are listed in alphabetical order and a number or an “N” is assigned to each one, lowest number to functional group

26 Naming Quaternary Ammonium Salts

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28 Structures of Alkyl Halides

29 Structures of Alcohol and Ether

30 Structures of Amines

31 The greater the attractive forces between molecules, the higher is the boiling point of the compound Attractive Forces van der Waals force Dipole–dipole interaction Hydrogen bonds

32 van der Waals Forces The boiling point of a compound increases with the increase in van der Waals force

33 Dipole–Dipole Interaction Dipole–dipole interactions are stronger than van der Waals force but weaker than ionic or covalent bonds

34 A hydrogen bond is a special kind of dipole–dipole interaction

35 Boiling Points

36 Like Dissolves Like Polar compound dissolves in polar solvent Nonpolar compound dissolves in nonpolar solvent

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38 Conformations of Alkanes: Rotation about Carbon–Carbon Bonds

39 Torsional strain: repulsion between pairs of bonding electrons A staggered conformer is more stable than an eclipsed conformer Different Conformations of Ethane

40 Conformations of n-Butane Steric strain: repulsion between the electron clouds of atoms or groups

41 Cycloalkanes: Ring Strain Angle strain results when bond angles deviate from the ideal ° bond angle

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43 The chair conformation of cyclohexane is free of strain

44 The Conformations of Cyclohexane and Their Energies

45 The Conformations of Cyclohexane and Their Energies