1. Chemical bond and structure of organic compounds
Lecture 1

2. Outlook Organic and inorganic compounds
Structure of organic compounds and the nature of chemical bond
Nomenclature of organic compounds

3. Organic and inorganic compounds
combustion analysis:
water
carbon dioxide
gases and minerals
Antoine Laurent Lavoisier
two types of matter:
organic
inorganic

4. Organic and inorganic compounds
Jöns Jacob Berzelius
Friedrich Wöhler
NH4OCN → (NH2)2CO
Organic chemistry (1807) – study of compounds from natural sources
Vitalism – organic compounds can only be produced by the vital force
ammonium
cyanate
INORGANIC
urea
(carbamide)
ORGANIC
CH4N2O
isomers – different materials – same composition

5. Structure of chemical compounds
Isomers – different materials – same composition – different structure
August Kekulé
Alexander Butlerov
1858: Carbon atom normally forms four bonds
1858: chemical structure – the way in which atoms are connected determines the nature of compounds

6. The nature of chemical bond
Gilbert Lewis
chemical bond – a shared pair of electrons

7. The nature of chemical bond
atomic number 6
6 protons in the nucleus
6 electrons in the shell
1s22s22p2

8. the orbitals mix - undergo hybridization
four bonds in methane are formed using different electrons, but the bonds are completely equivalent
the orbitals mix - undergo hybridization

9. Hybridization
1954, 1962
Linus Pauling

10. sp3 hybridization

11. sp2 hybridization
ethylene

12. sp hybridization
acetylene

13. Hybridization
Now let’s look at the hybridization of nitrogen and oxygen atoms…

14. Classes of organic compounds
Functional group - a characteristic group of atoms/bonds that possess a predictable chemical behavior

15. Classes of organic compounds

16. Classes of organic compounds
Determine the class of organic compounds

17. Nomenclature of organic compounds – trivial names
“What's in a name? that which we call a rose By any other word would smell as sweet.”
 William Shakespeare
Acetone
spirit of Saturn
Formic acid
Raspberry ketone
Squaric acid
Butyric acid
cubane
Olympicene

18. Systematic nomenclature of organic compounds
Name of an organic compound:
parent chain
substituents – radicals and functional groups
multiple bonds
geometric and space configuration
Names of hydrocarbons
Number of Carbons
Name
Radical 1
methane
methyl 2
ethane
ethyl 3
propane
propyl 4
butane
butyl 5
pentane
pentyl 6
hexane
hexyl 7
heptane
heptyl 8
octane
octyl 9
nonane
nonyl 10
decane
decyl 11
undecane
undecyl 12
dodecane
dodecyl

19. Systematic nomenclature of organic compounds
Simple steps:
Identify the longest carbon chain - the parent chain
Identify all of the parent functional group (highest in precedence)
Identify all of the side chains and other functional groups
Identify double/triple bonds
Number the carbons of the parent chain from the end that gives the parent functional group/multiple bonds/side chains the lowest numbers
Compose the name:
functional groups and side chains (alphabetically), indicate locations and the number of substituents (di, tri, tetra, etc.)
parent chain
double/triple bonds with numbers
primary functional group

20. Order of precedence of functional groups
Priority
Functional group
Prefix
Suffix 1 -
-oic acid 2
cyano-
-nitrile 3
formyl-
-al 4
oxo-
-one 5
hydroxy-
-ol 6
amino-
-amine 7
nitro-