1. Topic 11 Review Book Tables P, Q and R
Organic Chemistry
Topic 11 Review Book
Tables P, Q and R

2. What is Organic Chemistry?
study of carbon and the compounds that it forms
carbon has 4 valence electrons so it will form 4 covalent bonds- lends itself to a great variety of compounds
May also contain but are not limited to the following elements:
Oxygen e) Phosphorus
Nitrogen f) Sulfur
Fluorine g) hydrogen
Bromine

3. Properties of Organic Compounds
Covalent bonds
generally nonpolar- what does that mean?
insoluble in water
low mp’s and bp’s: boiling point is directly related to the length of carbon chain
nonelectrolytes
slow to react because of the covalent bonds – many reactions require a catalyst
Hundreds of thousands of organic compounds because C can form so many bonds

4. Quick Review How many valence electrons does an atom of carbon have?
How many bonds can an atom of carbon make?

5. Types of Organic Formulas
Molecular – how many atoms and what elements are in a molecule. Ex. C3H8
Structural Formula – shows how the atoms in the molecule are bonded, Ex. C3H8
Condensed Structural Formula – emphasizes groups of the atoms in the molecule Ex 1. CH3CH2CH3 

6. Draw a Lewis structure for CH4
Draw C2H Draw C6H14

7. Hydrocarbons (Tables P and Q)
molecules that contain only carbon and hydrogen
May have single, double or triple bonds
May form straight chains, branched chains or rings
homologous series  different groups of hydrocarbons
each group contains molecules that have similar structures and properties
as the molecular mass increases, the boiling point increases (why?)

8. 1. Alkanes Only single bonds Saturated the general formula is CnH2n+2
End in –ane
Prefix tells you the number of carbon atoms
Example: Methane, Ethane, Propane, etc
May be straight or branched chains

9. 2. Alkenes One double bond (C = C) rest are single Unsaturated
The general formula is CnH2n
First member is ethene
Examples: Propene, Butene, Pentene
May be straight or
branched chains

10. 3. Alkynes one triple bond, the rest are single unsaturated
the general formula is CnH2n-2
First member is ethyne
Example: Propyne, Butyne,
Pentyne
May be straight or branched

11. Aromatic Hydrocarbons
Made up of a chain of hydrocarbons that form a ring
Most common one is benzene
C6H6 in a ring of alternating double
And single bonds

12. Saturated vs Unsaturated
Saturated hydrocarbons have ________________
Unsaturated hydrocarbons have ______________
Many hydrocarbons have isomers

13. Isomers
Isomers - molecules that have the same molecular formula but a different structural formula
Isomers of hydrocarbons differ in the length of the carbon chain or the position of a double or triple bond
Ex. C4H10 is an alkane that has 2 isomers
They will have different properties

14. Using Table P 1. How many carbon atoms are in each hydrocarbon?
 a) methane ____ f) hexane ____ k) decane ____
 b) ethane ____ g) ethyne ____ l) butyne ____
 c) ethene ____ h) propane ____ m) butene ____
 d) pentane ____ i) heptane ____ n) propyne ____
 e) propane ____ j) octene ____ o) butane ____

15. Using Table P and Q Compound # of Carbons SERIES General FORMULA
Ex: Butane  4  Alkanes  C4H10
a) methane  ___________  _________ ___________
b) butene  ___________  _________ ____________
c) propyne  ___________  _________ ____________
d) pentane  ___________  _________ ____________
e) octane   ___________  _________ ____________
f) heptene  ___________  _________ ____________
g) propene   ___________  _________ ____________

16. Naming and Drawing Straight Chain Alkanes
Without Branches
identify the number of carbons
use table P to get the prefix for that number
add the suffix “ane”
Ex: CH4= “meth” + “ane” = methane
ethane
propane
Butane
Pentane
Hexane
octane

17. Naming and Drawing Straight Chain Alkenes
Alkenes without branches
Name alkenes the same way you would alkanes, EXCEPT you must specify the location of the double bond by using the lower number of the two that it is in between
Examples:
Ethene
Propene
Butene (1 Butene, 2 Butene)
Pentene (1 Pentene, 2 Pentene,)

18. Naming and Drawing Alkynes
The rules for naming alkynes are the same for alkenes, except there is a triple bond instead of a double bond
2-butyne
2-hexyne
3 hexyne
1 pentyne
3 octyne

19. Naming and Drawing Branched Alkanes
You need to be able to identify three things: Parent chain, branch name, location
Example
1. Identify the longest continuous chain (parent chain)- use table P for the prefix and add -ane 2. Find the branches 3. Number the carbons in the parent chain, starting at the side closest to the branch 4. Count the number of carbon atoms in the branch and get the prefix from Table P and add the suffix –yl 5. Use the number of the parent carbon atom, the name of the side chains and the name of the parent chain
4 ethyl octane

20. Naming Branched Alkanes
If the same group occurs more than once as a side chain, you indicate this using prefixes (ex: di, tri). Indicate the positions of each group with a number
If the side chains are different, name the one with the smallest carbon number first
2,3 dimethyl pentane

21. Naming and Drawing Branched Alkenes and Alkynes
follow the same rules for naming branched alkanes, EXCEPT when numbering the carbons, start with the side closest to the double bond or triple bond rather than the nearest side chain

22. Functional Groups – Replacement of One or More H
Other types of organic compounds can form when different atoms replace one or more of the hydrogens
happens to alkanes
These atoms or groups of atoms are called functional groups
They give the compound specific physical and chemical properties

23. 1. Halides
When one of the halogens (F, Cl, Br, I) replaces a hydrogen atom
called a halide or a halocarbon
The functional group is the halogen
Naming: Specify the location of the halogen and use the following prefixes: chloro, fluoro, bromo, iodo
Uses: Teflon, Freon, CFC’s, dry cleaning solvents, pesticides

24. 2. Alcohols
a hydrogen on an alkane is replaced with an -OH group (hydroxyl group- NOT hydroxide ion!)
the functional group is –OH
Classified according to the number of carbons bonded to the carbon where the –OH is
Primary, secondary, tertiary
Naming: Drop the “e” and add “ol”; specify the location of the –OH
Uses: fuel, solvents, industrial feedstock (used to make other products, such as formaldehyde, etc)

25. 3. Ethers The functional group is -O-
Naming: you name the left group and the right group and you follow it by the word ether
if both group are the same, use "di“
Used to be used as anesthetics

26. 4. Aldehydes contain a carbonyl (C=O) group on an end carbon
No numbering
Naming: Drop the “e” and add “al”

27. 5. Ketones Carbonyl group on any carbon atom except the end ones
Formed by the oxidation of a secondary alcohol
Naming: drop the “e” and add “one”, specify the location

28. 6. Organic Acids
The functional group is -COOH which is called a carboxyl group
Usually formed by oxidizing alcohols
Carboxyl groups are only attached to end carbons, so no numbering is needed
Naming: drop the “e” and add “oic acid”

29. 7. Esters
They are formed from a reaction between a carboxylic acid and an alcohol
Naming: The name of the alcohol is given first, with the suffix changed to “yl”
Then the name of the acid is given with the suffix changed to “oate”

30. 8. Amines 9. Amides The functional group is -NH2 called an amino group
Naming: drop the “e” and adding “amine”, specify location
9. Amides
They contain an amino group attached to the carbon atom of a carbonyl group
Naming: drop the “e” and add “amide”

31. 1. Substitution
replacement of one or more hydrogen atoms in an alkane with another atom or group
ex. halogen atoms replace a hydrogen atom on an alkane to make a halide and an acid
ex. C2H6 + Cl2  C2H5Cl + HCl

32. 2. Addition
involves adding one or more atoms at the site of a double or triple bond
occurs in alkenes or alkynes
Ex. C2H4 + Cl2  C2H4Cl2

33. 3. Hydrogenation type of addition
it is the addition of hydrogen to an unsaturated compound to make it saturated
it requires a catalyst and a raised temp
Ex. C2H4 + H2  C2H6

34. 4. Esterification
the reaction of an organic acid with an alcohol to produce an ester plus water
slow reaction that is reversible
usually have pleasant odors

35. 5. Saponification
when an ester (fat) reacts with an inorganic base (NaOH) to produce an alcohol and a soap

36. 6. Polymerization
the formation of large molecules called polymers by combining smaller units called monomers
used to make plastics and rubber, proteins, starches and cellulose
Condensation polymerization: the bonding of monomers by a dehydration reaction
ex. glucose + glucose  sucrose + water
Addition polymerization: the joining of monomers by eliminating double or triple bonds
Ex. ethene + ethene = butane

37. 7. Fermentation
when yeast breaks down 6-carbon sugars to produce carbon dioxide and an alcohol
ex. C6H12O6  2C2H5OH + CO2

38. 8. Combustion (and so...we end as we began)
When a saturated hydrocarbon reacts with oxygen to produce water and carbon dioxide
A lot of energy (heat) is given off
C3H6 +5O2  3CO2 + 4H2O

39. Lastly… Practice your regents exams Use the Barron’s book
Bring a NON-GRAPHING calculator, a black pen and pencil (for drawing) to the Regents Exam
Have a great summer and come back to visit next year!