1. Ch 25 Hydrocarbon Compounds

2. Carbon
Make a list of everything you know of that contains carbon:

3. Ch 25.1 Hydrocarbons Organic Chemistry Straight Chain Alkanes
Branched Chain Alkanes
Properties of Alkanes

4. Organic Chemistry Chemistry of all carbon compounds
Over 1 million compounds
Hydrocarbons – organic compounds with only carbon and hydrogen
Alkanes – simplest hydrocarbons

5. Methane

6. Methane
CH4
Carbon always forms 4 covalent bonds

7. Straight Chain Alkanes
A number of carbon atoms, one after another
Ethane

8. Reference Table
Table Q – Types of Hydrocarbons
Table P - Prefixes

9. Name Structural Formula Methane CH4 Ethane C2H6 Propane C3H8 Butane
Molecular Formula
Structural Formula
Methane
CH4
Ethane
C2H6
CH3CH3
Propane
C3H8
CH3 CH2 CH3
Butane
C4H10
CH3 CH2 CH2 CH3
Pentane
C5H12
CH3 CH2 CH2 CH2 CH3
Hexane
C6H14
CH3 CH2 CH2 CH2 CH2 CH2 CH3
Heptane
C7H16
CH3 CH2 CH2 CH2 CH2 CH2 CH2 CH3
Octane
C8H18
CH3 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH3
Nonane
C9H20
CH3 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH3
Decane
C10H22

10. Branched Alkanes
Substituent – atom or group of atoms that takes the place of as hydrogen atom
An alkane with one or more branched groups

11. Ch 25.2 Unsaturated Hydrocarbons
Alkenes
Alkynes

12. Alkenes
Hydrocarbons containing carbon to carbon double bonds

13. Saturated vs. Unsaturated
Saturated – organic compound in which all carbon atoms are joined by single covalent bonds, contains the maximum number of hydrogen compounds
Unsaturated – organic compound with one or more double or triple carbon-carbon bonds

14. Alkynes
Hydrocarbon containing carbon to carbon triple bonds

15. Ch 25.3 Isomerism
Isomer – same molecular formula, different structural formula

16. Chapter 25.4 Hydrocarbon Rings
Cyclic Hydrocarbons
Aromatic Hydrocarbons

17. Cyclic Hydrocarbons
Compounds where the end carbon of the chain are attached to each other forming a ring
Aliphatic Compounds – hydrocarbon that are chains, not rings

18. Aromatic Hydrocarbons
Arenes – unsaturated cyclic hydrocarbons, contain single rings or groups of rings
Aromatic Compound – any substance in which the bonding is like benzene

19. Benzene
C6H6

20. Chapter 25.5 Hydrocarbons from Earth
Natural Gas
Petroleum
Coal

21. Fraction
Carbon Chains
Boiling Range (0C)
Percent Crude Oil
Natural Gas
1-4
Below 20 10
Petroleum Ether
5-6
30-60
Naptha
7-8
60-90
Gasoline
6-12
40-175 40
Kerosene
12-15
Fuels Oils
15-18 30
Grease, Tar
16-24
Over 400

27. The graph below shows the relationship between boiling point and molar mass at standard pressure for pentane, hexane, heptane, and nonane.
Octane has a molar mass of 114 grams per mole. According to this graph, what is the boiling point of octane at standard pressure?
State the relationship between molar mass and the strength of intermolecular forces for the selected alkanes.

28. Allow 1 credit. Acceptable responses include, but are not limited to:
Allow 1 credit for 124°C ± 2°C.
Allow 1 credit. Acceptable responses include, but are not limited to:
As molar mass increases, there are stronger intermolecular forces.
The forces are greater between heavier molecules.

29. The compound 1,2-ethanediol can be mixed with water
The compound 1,2-ethanediol can be mixed with water. This mixture is added to automobile radiators as an engine coolant. The cooling system of a small van contains 6690 grams of 1,2-ethanediol. Some properties of water and 1,2-ethanediol are given in the table below.
Identify the class of organic compounds to which 1,2-ethanediol belongs.
State, in terms of molecular polarity, why 1,2-ethanediol is soluble in water.
In the space in your answer booklet, calculate the total number of moles of 1, 2-ethanediol in the small van’s cooling system. Your response must include both a correct numerical setup and the calculated result.

30. Acceptable responses include, but are not limited to:
Allow 1 credit. Acceptable responses include, but are not limited to: alcohol
Acceptable responses include, but are not limited to:
Water and 1,2-ethanediol molecules are both polar.
Both molecules have similar polarity.
• Allow 1 credit for a correct numerical setup. Acceptable responses include, but are not limited to:
• Allow 1 credit for 108 mol or for a response consistent with the student’s numerical setup.

31. A gasoline engine burns gasoline in the presence of excess oxygen to form carbon dioxide and water. The main components of gasoline are isomers of octane. A structural formula of octane is shown below.
One isomer of octane is 2,2,4-trimethylpentane.
In the space in your answer booklet, draw a structural formula for 2,2,4-trimethylpentane. [1]
Explain, in terms of the arrangement of particles, why the entropy of gasoline vapor is greater than the entropy of liquid gasoline.

32. The arrangement of molecules in the vapor state are more random or disordered.
Particles in the vapor state are farther apart and move more freely.

33. Chapter 26 Functional Groups
Halide (Halocarbons)
Alcohols
Ethers
Aldehydes
Ketones
Carboxylic Acids
Esters

34. Halide (Halocarbons)
Organic compounds covalently bonded with fluorine, chlorine, bromine, or iodine
Naming: number – halide prefix – name
1- Chlorohexane
R – X (X = any halogen)

35. Alcohols Organic compounds with an –OH group
- OH group = Hydroxyl group
Naming: number – name – ol ending
2 - butanol

36. Primary, Secondary, Tertiary Alcohols
Primary Alcohol – only 1 carbon attached to the primary C – OH
R – CH2 – OH
Secondary Alcohol – 2 carbons attached to the primary C – OH
R – CH – OH R
Tertiary Alcohol – 3 carbons attached to the primary C – OH
R – C – OH

37. Ethers Organic compound in which oxygen is bonded to two carbon groups
R – O –R
Naming: name each group on each side of the oxygen, then use alphabetical order and ends with ether
CH3CH2OCH3
Ethyl methyl ether

38. Aldehydes
Organic compound in which the carbon of the carbonyl group is bonded with at least one hydrogen
R-CH-O
Naming: name the longest chain, drop the e ending, add al
H – C = O H
Methanal

39. Ketones
Organic compound in which the carbon of the carbonyl group is bonded to two other carbons
R – C =O R
Naming: Naming: name the longest chain, drop the e ending, add one

40. Carboxylic Acids Organic compound with a carboxyl group R – C =O OH
Naming: Drop the e add oic acid
RCOOH

41. Esters Carboxylic acid with the OH replaced by an OR R – C = O O – R
Naming: drop the e, add oate

42. Dehydration Synthesis
The linking of two organic compounds by removing water from functional groups.

43. Etherification a) requires 2 alcohols
b) H2SO4 is the dehydrating agent. It removes H from one alcohol molecule and OH from the other to form H2O.

44. Esterification a) requires an alcohol and a carboxylic acid
b) forms an ester, named for the alcohol and acid that formed it.

46. Fermentation
Fermentation of glucose or fructose in corn, barley, grapes, apples, etc. forms ethanol:
The reaction proceeds until the alcohol content reaches 13%, at which point the yeast dies. Further increases in concentration may be yielded by distillation. Used in alcoholic beverages where, in the synthesis of acetic acid (by catalytic oxidation) and it is used as a solvent.

47. Saponification The production of soap.
a) Requires a glycerol ester (fat) and sodium hydroxide (strong base)
b) The glycerol ester is dissolved in ethanol, and the NaOH is mixed in.
c) The mixture is heated slowly until it thickens.
d) The alcohol solvent is now evaporated off.
e) The resultant mixture is glycerol plus the sodium salts of the long-chain acids. The salts represents the soap.
f) The salts may be precipitated out of the glycerol by adding NaCl and filtering out the glycerol. The resulting lump is soap.

49. Polymerization
POLYMER - an extremely large molecule made by connecting many smaller molecules together. The basic molecules used as "building blocks" of the polymer are called monomers.
Monomer molecule = A
polymerization
18 A -> A-A-A-A-A-A-A-A-A-A-A-A-A-A-A-A-A-A
Can be abbreviated as 18 A -(-A-)-18, which represents a chain of A monomers 18 units long.

50. Types of Polymers:
1) Addition Polymers - formed by addition polymerization reaction: the monomer’s double bond opens, allowing
the monomer units to join end to end. The name of the polymer is found by putting a “poly” in front of the monomer’s
name. For example, propylene monomer forms polypropylene.

51. Polyvinyl Chloride
1. Formed from Vinyl Chloride monomer (chloro ethane)
2. The double bond breaks, and VC monomer units join end to end.
3. Used for water pipes, record albums, raincoats, shower curtains, wire insulation, vinyl siding

53. Polystyrene
1. Formed from styrene monomer (phenyl ethane, basically ethene with a benzene attached to it)
2. The double bond breaks, and styrene monomer units join together.
3. Used for plastic model kits, styrofoam

55. Polytetrafluoroethene (teflon)
1. Formed from tetraflouro ethene monomer
2. The double bond breaks, and TFE monomer units join together.
3. Used for no-stick pans.
4. Accidentally discovered in 1938 by Roy Plunkett.

57. Types of Polymers:
2) Condensation Polymers - formed by dehydration synthesis of difunctional monomer units. H and OH are removed
from the ends of the monomer units, allowing them to join together. Water is given off as a byproduct.

58. Polyester
1. Formed from monomer units that have an alcohol functional group on one end and a carboxylic acid functional
group on the other end.
2. The opposing ends undergo dehydration synthesis, and form the polymer.

60. Types of Polymers: 3) Rubber
a) cis- Polyisoprene (tires), polybutadiene (tires), polychloropropene (Neoprene...wire covering, automotive drive belts,
wetsuit material)), Nitrile (automotive hoses and gaskets)
1. Formed by addition polymerization
2. The resultant macromolecule is tacky and not very strong. It generally has a low melting point.
3. In order to make this stuff serviceable, it must by toughened up. This is done by a process whereby the polymer chains are cross-linked with sulfur. This toughens up the rubber. This process was discovered accidentally by Charles Goodyear in This process is called vulcanization.
Unfortunately, when heat is applied to rubber so treated, it does not melt, but burns, releasing CO, CO2 and SO2.

62. Recognize a reaction

63. Determine reactants to make the desires product: