Transcript Organic Chemistry

ORGANIC
CHEMISTRY
Organic Chemistry
• Study of carbon and carbon compounds
• Organic compounds contain carbon
atoms which covalently bond to each
other in chains, rings, and networks to form
a variety of structures
General Characteristics of Organic
Compounds
• Nonpolar
• Soluble in nonpolar solvents / insoluble in
polar solvents (water) “Like dissolves Like”
• Poor conductors of heat and electricity
– Exception: aqueous organic acids conduct
• Low melting and boiling points
• React slower than inorganic compounds
• Structural Formulas
– Attempts to show the bonding patterns and
approximate shapes
– Ex:
• Condensed Structural Formulas
– Shows the connections without showing the
shape and bonds
– Ex:
Bonding
• Carbon- has 4 valence electrons, needs 4 more,
forms 4 bonds
• Hydrogen – has 1 valence electron, needs 1 more,
forms 1 bond
• Oxygen – has 6 valence electrons, needs 2 more,
forms 2 bonds
• Nitrogen – has 5 valence electrons, needs 3 more,
forms 3 bonds
• Halogens (group 17) – has 7 valence electrons,
needs 1 more, forms 1 bond
Homologous Series (Families)
• Group of related compound in which each
member has one more group
– Ex: CH3CH2CH3 and CH3CH2CH2CH3
• Members of a group will have similar structures
and properties
• As the members of a series increase in mass, their
boiling (and melting) points increase – due to
increased intermolecular forces
Hydrocarbons
• Organic compounds that contain only
CARBON and HYDROGEN
ALKANES...
SINGLE bonds between Carbons
Saturated hydrocarbon
CnH2n+2
Family Name
ALKENES...
ONE DOUBLE bond between two Carbons
ALKYNES...
ONE TRIPLE bond between two Carbons
Unsaturated hydrocarbon
Unsaturated Hydrocarbon
CnH2n
CnH2n-2
PREFIXES
…counting the CARBONS
ALKANES
• Contain all single bonds
• Naming: carbon prefix + -ane
Examples:
Butane
Octane
ALKENES
• Contain 1 double bond
• Naming: carbon prefix + -ene
– A number is used in front to indicate the
location of the double bond
– If a number is not indicated the double bond
comes after the 1st carbon
Example: 2-Pentene
Diene
• Contains 2 double bonds
• Naming: location-carbon prefix-diene
• Example: 1,3-pentadiene
ALKYNES
• Contains 1 triple bond
• Naming: location - carbon prefix + -yne
Examples:
3 – hexyne
Propyne
• Saturated Compounds – contains all single
carbon-carbon bonds
• Unsaturated Compounds – contains at least
one multiple carbon-carbon bond
Branched Hydrocarbons
• Contain 1 or more branches off the main chain
Methyl group on carbon 4
8
7
6
5
4
3
2
4-methyl-ocatane
1
Naming Branched Hydrocarbons
• Find the longest continuous chain, name it
• To name the branches: number of carbons + “-yl”
– Examples:
• CH3 = methyl
• CH2CH3 = ethyl
• The location of the alkyl (branched group) is
indicated
– If there is more than one of the same branch, use
prefixes (di, tri, tetra, …)
– The carbon chain must be numbered from the end that
will give the lowest numbers for the branches
Example: 2, 2, 3 – trimethyl pentane
SAME…BUT DIFFERENT
• Same – number and type of atoms
• Different – structure and name
Have different physical and chemical properties
2 CARBONS
6 HYDROGENS
1 OXYGEN
ETHANOL
DIMETHYL ETHER
a primary alcohol
C2H5 OH
CH3OCH3
GROUPS
and
COMPOUNDS
• Functional Group: halogen (group 17 element)
• Name: location-halide-carbon chain
• Examples:
1. 2-bromobutane
2. 1,3 - dichloropentane
ALCOHOLS
•
•
•
•
•
Functional Group: -OH
No more than one –OH group can be attached to any one
carbon
The carbon to which the –OH group is attached must have all
single bonds
Alcohols are not bases (do not ionize in water)
Name: hydrocarbon name, replace the final –e with –ol
Examples:
1. Methanol
2. 2-Propanol
Types of Alcohols
• Monohydroxy – contain 1 –OH group
– Primary
– Secondary
– Tertiary
• Dihydroxy (Diol) – contain 2 –OH groups
• Trihydroxy (Triol) – contain 3 –OH groups
Primary Alcohols
•
•
•
Contain 1 –OH group
-OH group is attached to the end of the
chain
Examples:
1. Ethanol
2. Propanol
H
SECONDARY ALCOHOL
•Contain 1 –OH group
R-C-R
O
H
•Carbon that is attached to the –OH group is
attached to 2 other carbon atoms
2-Butanol
R
TERTIARY ALCOHOL
•Contain 1 –OH group
R-C-R
O
H
•Carbon attached to the –OH group is attached
to three other carbon atoms
2METHYL,2-BUTANOL
2 -OH groups are present
Example: 1,2 ethanediol
3 -OH groups are present
Example: 1,2,3 propanetriol
•Functional Group = -COOH
•Name: Hydrocarbon name, drop the final “e” and
replace it with “–oic” followed by the word “acid”
•Examples:
1. Ethanoic Acid
2. Butanoic Acid
• Functional Group: -CHO
• Name: drop the final “e” and add “-al”
ethanal
2 carbons
alkane aldehyde
Propanal
• Functional Group: -CO• Name: Hydrocarbon name, drop the final “e”, add
“one”
Propanone
2-Butanone
• Functional group: -O- (chain-O-chain)
• Name:
1. Name each hydrocarbon chain – drop the
ending add “yl”
2. Add “ether” to the end
diethyl ether
Ethyl methyl ether
• Functional Group: -COOR
• Formed from a dehydration reaction of an alcohol
and an acid
• Fruity odor
• Name:
• Name each hydrocarbon chain
– The part with the –CO gets the “-oate” ending
– The other part gets the “-yl” ending
Ester Examples
• Ethyl Methanoate
• Ethyl Ethanoate
• Functional Group: NH2
• Name the chain, add “amine” to the end
ethanamine
C2H5NH2
• Functional Group: R-CONH2
• Name: Name the chain, add “amide” to the
end
Butanamide
Propanamide
• Functional Groups: -NH2 and –COOH
• Just like an alcohol, but –SH instead of –
OH
Example: Methyl Thiol (CH3SH)
SUBSTITUTION
ADDITION
ESTERIFICATION
SAPONIFICATION
POLYMERIZATION
COMBUSTION
FERMENTATION
• Something takes the place of
something else
• Starts with a saturated
hydrocarbon
• 2 reactants, 2 products
Ethane
Chlorine
•
•
•
•
Start with an unsaturated hydrocarbon
Break the double (or triple) bond
Add in an atom (or group)
2 reactants, 1 product
Ehtene
Cl2
1,2 Dichloroethane
Concentrated H2SO4
acts as a dehydrating agent
ORGANIC ACID + ALCOHOL
Propanoic
Acid
H2SO4
Methanol
ESTER +
WATER
Methyl
Propanoate
H 2O
• Reverse of esterification, carried
out in the presence of a base
FAT
(glycerol ester)
Strong base
(NaOH or KOH)
SOAP
glycerol
(trihydroxy alcohol)
1,2,3 propane triol
C6H12 O6
GLUCOSE
enzyme
C2H5 OH
ETHANOL
CO2
CARBON
DIOXIDE
• Hydrocarbon + O2
• Exothermic
Example:
C2H6 + O2
CO2 + H2O
Poly...poly...poly…poly...poly...polymerization
• Chains of small units make up a
MACROMOLECULE
• Examples: Plastics, proteins
Condensation Polymerization
• Bonding of monomers by a dehydration
reaction
– OH groups of adjacent alcohols react, water is
removed, the 2 molecules are connected by the
remaining O
• Examples: Nylon, Protein, Polyester
Addition Polymerization
• Bonding of monomers of unsaturated
compounds by “opening” a multiple bond in
the carbon chain
• Example: polyethylene and many plastics
n C 2H 4
(C2H4)n