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Hydrocarbons

Unsaturated hydrocarbons
– Double and triple bonds between carbons
– Not every carbon has each of its 4 electrons
bonded to 4 different atoms
– More chemically reactive than saturated
compounds, or alkanes
– Unsaturated hydrocarbons include alkenes
(double bonds) and alkynes (triple bonds)

Mullis 1
Naming Organic Compounds
1. Name the parent hydrocarbon: Use the
LONGEST STRAIGHT chain of carbon atoms.
2. Add the name of the alkyl groups attached to the
chain. If more than one group is attached, use
the proper numerical prefix to indicate how many
groups are attached. (2=di, 3-tri,etc.)
3. Assign numbers to the carbons in the parent
chain. Assign so that attached groups are at the
lowest number possible.
4. Insert the numbers in front of the proper group.
5. Separate position numbers from names with
hyphens. Mullis 2
Example: Naming Organic Compounds
1. Name the parent hydrocarbon.
CH3 – CH – CH2 – CH – CH – CH3 hexane
CH3 CH3 CH3
2. Add the name of the alkyl groups attached to the chain.
3 methyl groups: trimethylhexane
3. Assign numbers to the carbons in the parent chain.
6 5 4 3 2 1
CH3 – CH – CH2 – CH – CH – CH3
CH3 CH3 CH3
4-5. Insert position numbers and add hyphens.
2,3,5-trimethylhexane

Mullis 3
Name the following compounds
1. CH3 – CH – CH2 – CH2 – CH3
CH3

2. CH3 – CH – CH2 – CH2 – CH – CH3


| |
CH3 CH3

3. CH3 – CH – CH2 – CH2 – CH3


CH2
CH2 Mullis 4
Unsaturated hydrocarbons
• Single bond between carbons: -ane CnH2n+1
• Double bond between carbons: -ene CnH2n
• Triple bond between carbons: -yne CnHn
• Examples:
H H H H
H C C H C C H C C H
H H H H
ethene ethyne
ethane C2H4 C2H2
C2H6
Mullis 5
Other Functional Groups
Compound Formula Example

Alcohol R-OH hydroxyl group 1-propanol

Alkyl Halide -X X = any halide 1,2-dibromopropane

Ether R-O-R’ one oxygen bonded to 2 diethyl ether


CH3-CH2 –O--CH2--CH3
hydrocarbon groups
Aldehyde O Carbonyl group attached to Ethanal O
||
|| end carbon CH3—C--H
R-C-H
Ketone O Carbonyl group attached to 2-propanone O
||
|| a middle carbon CH3—C-- CH3
R-C-R’
Carboxylic Acid O Carboxyl group ethanoic acid O
||
|| CH3—C—OH
R-C-OH
Ester O Carboxyl group without the methyl ethanoate O
||
|| H CH3—C—O-- CH3
R-C-O-R’

Mullis 6
Cyclic Compounds
• Cycloalkanes
– Saturated carbons joined in a ring
– Example is cyclohexane, C6H12
– Add cyclo- to beginning of name if the alkane is known to be
arranged in a circle (CnH2n ). No position number is needed if
only one alkyl group is attached.
• Aromatic compounds
– Unsaturated: Contains 3 double bonds
– Example is benzene, C6H6
H-C C-H
H-C C-H
CH3CH2- -CH3
H-C C-H
1-ethyl-4-methylbenzene benzene
Mullis 7
Addition Reactions
• Water adds to ethene: The double bond is broken and
an H attaches to one carbon and the OH attaches to the
other carbon.
H H HH
C C + H-OH H-C-C-H
H H HH
• Ethene can add to itself, breaking double bonds to
attach to one molecule after another.

• A monomer is a small unit; when additional


monomers are attached repeatedly, a long-chain
polymer is formed.
Mullis 8
Addition Polymers
• Polyethylene is a polymer made from the monomer
ethene. Zip-lock bags are usually made from low-
density polyethylene.
• Common polymer variations replace one of ethene’s
hydrogens with another unit, such as a halogen atom
(F or Cl), Cyanide (CN), or benzene (C6H6).
– Vinyl chloride polyvinyl chloride
– Acrylonitrile polyacrylnitrile
– Styrene polystyrene
• Atoms that compose the monomers determine the
properties of the polymer.
Mullis 9
Petrochemicals
• Petrochemicals are compounds produced from
oil or natural gas.
• Most are used to produce other synthetic
products, especially plastics.
• Builder molecules are those small-molecule
compounds such as ethene.
• Ethene is a 2-carbon hydrocarbon with a
double bond (2 pairs of shared electrons).
• Compounds with double and triple bonds are
more reactive than those with single bonds. 10
Mullis

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