1. Organic Chemistry
Chapter 22

2. Organic Chemistry
The study of carbon-containing compounds and their properties.
The vast majority of organic compounds contain chains or rings of carbon atoms.

3. Organic & Inorganic Compounds
Originally the distinction between inorganic and organic substances was based on whether or not they were produced by living systems.
In 1828, German chemist Friedrich Wohler prepared urea from the inorganic salt ammonium cyanate by simple heating:
heat
NH4OCN ---> NH2CONH2

4. Hydrocarbons . . . compounds composed of carbon and hydrogen.
Saturated: carbon-carbon bonds are all single - alkanes [CnH2n+2]

5. Hydrocarbons (continued)
Unsaturated: contains carbon-carbon multiple bonds.

6. C2H4(g) + H2(g) ---> C2H6(g)
Hydrogen Addition
C2H4(g) + H2(g) ---> C2H6(g)
unsaturated saturated

7. The carbon-hydrogen bonds in methane.

8. The Lewis structure, space-filling, and ball-
and-stick models for ethane.

9. The structures of propane and butane with 109.5o
bond angles.

10. Structural Isomerism
-- isomers contain the same atoms but one or more different bonds.

11. Normal butane (n-butane) and the branched
isomer, isobutane.

12. Isomers of Pentane What are the three isomers of pentane?
1) n-pentane -- straight-chain
2) isopentane -- one branch from 2nd carbon
3) neopentane -- two branches from central carbon

13. The straight-chain isomer, n-pentane.

14. Rules for Naming Alkanes
1. For alkanes beyond butane, add -ane to the Greek root for the number of carbons.
C-C-C-C-C-C = hexane
2. Alkyl substituents: drop the -ane and add -yl.
-C2H5 is ethyl

15. Rules for Naming Alkanes
3. Positions of substituent groups are specified by numbering the longest chain sequentially. C 
C-C-C-C-C-C
3-methylhexane
4. Location and name are followed by root alkane name. Substituents in alphabetical order and use di-, tri-, etc.
See Sample Exercise 22.2 on pages

16. Combustion Reactions of Alkanes
C3H8(g) + 5O2(g) ----> 3CO2(g) + 4HOH(g)
2C4H10(g) + 13 O2(g) ----> 8CO2(g) + 10HOH(g)

17. Substitution Reactions for Alkanes
Primarily where halogen atoms replace hydrogen atoms.

18. Dehydrogenation Reactions
Cr2O3
CH3CH3 ----> CH2=CH2 + H2
500oC
ethane ethylene

19. Cyclic Alkanes
Carbon atoms can form rings containing only carbon-carbon single bonds.
C3H6, C4H8, C6H12
Shorthand notation for the cyclic alkanes.

20. The molecular structure of cyclopropane and
the overlap of the sp3 orbitals that form the
C-C bonds.

21. The chair and boat forms of cyclohexane.

22. Alkenes and Alkynes
Alkenes: hydrocarbons that contain a carbon- carbon double bond. [CnH2n]
CC=C propene
Alkynes: hydrocarbons containing a carbon- carbon triple bond. [CnH2n-2]
CCCCC pentyne

23. Nomenclature for Alkenes
1. Root hydrocarbon name ends in -ene
C2H4 is ethene
2. With more than 3 carbons, double bond is indicated by the lowest numbered carbon atom in the bond.
C=CCC is 1-butene

24. The bonding in ethylene.

25. The two stereoisomers of 2-butene.
a) cis-2-butene b) trans-2-butene

26. The bonding in ethane allows rotation and no
cis-trans isomerism.

27. The bonding in acetylene.

28. Addition Reactions
. . . in which (weaker)  bonds are broken and new (stronger)  bonds are formed to atoms being added.
propene propane

29. Halogenation CH2=CHCH2CH2CH3 + Br2 ---> CH2BrCHBrCH2CH2CH3
1-pentene ,2-dibromopentane

30. Aromatic Hydrocarbons
A special class of cyclic unsaturated hydrocarbons.
+ Cl2
+ HCl
benzene
Chlorobenzene

31. Aromatic Hydrocarbons
phenyl group
Ortho (o-) -- two adjacent substituents.
meta (m-) -- two substituents with one
carbon between them.
para (p-) -- two substituents opposite each other.

32. Refinery Processes
Cracking: large molecules broken down to smaller ones by breaking carbon-carbon bonds.
Pyrolysis (thermal cracking): The process that produces cracking at high temperatures.
Catalytic Cracking: Cracking at lower temperatures.
Catalytic reforming: Alkanes and cycloalkanes converted to aromatic compounds.

33. The Common Functional Groups
Class General Formula
Halohydrocarbons RX
Alcohols ROH
Ethers ROR
Aldehydes

34. The Common Functional Groups
Class General Formula
Ketones
Carboxylic Acids
Esters
Amines RNH2
Amides R-C=ONH2

36. Alcohols
contain the hydroxyl group (-OH).

37. Aldehydes & Ketones contain the carbonyl group ( C=O ).
In ketones the carbonyl group is bonded to two carbon atoms -- CH3C=OCH3.
In aldehydes the carbonyl group is bonded to at least one hydrogen atom -- HCHO.

38. Carboxylic Acids & Esters
Carboxylic acids contain the carboxyl group O
(-C-OH).
Esters contain the -C-O- group.

39. Amines & Ethers Amines contain -NH2 group.
If one hydrogen is removed and replaced with a hydrocarbon group, it is a primary amine.
If two hydrogen are replaced, it is a secondary amine.
If all three hydrogens are replaced, it is a tertiary amine.
Ethers contain the -O- group.

40. Polymers
. . . are large, usually chainlike molecules that are built from small molecules called monomers.
Monomer Polymer
Ethylene Polyethylene
Vinyl chloride Polyvinyl chloride
Tetrafluoroethylene Teflon

41. Types of Polymerization
Addition Polymerization: monomers “add together” to form the polymer, with no other products. (Teflon)
Condensation Polymerization: A small molecule, such as water, is formed for each extension of the polymer chain. (Nylon)