organic chemistry organic chemistry study of carbon and carbon compounds organic compounds contain...
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ORGANIC CHEMISTRY
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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
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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
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• 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:
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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
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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
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Hydrocarbons
• Organic compounds that contain only CARBON and HYDROGEN
ALKANES... SINGLE bonds between Carbons
Saturated hydrocarbonCnH2n+2
ONE TRIPLE bond between two Carbons
Unsaturated Hydrocarbon
ONE DOUBLE bond between two Carbons
Unsaturated hydrocarbonCnH2n
CnH2n-2ALKYNES...
ALKENES...Family Name
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…counting the CARBONSPREFIXES
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ALKANES
• Contain all single bonds
• Naming: carbon prefix + -ane
Examples:
Octane
Butane
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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
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Diene
• Contains 2 double bonds
• Naming: location-carbon prefix-diene
• Example: 1,3-pentadiene
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ALKYNES
• Contains 1 triple bond
• Naming: location - carbon prefix + -yne
Examples:
3 – hexyne
Propyne
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• Saturated Compounds – contains all single carbon-carbon bonds
• Unsaturated Compounds – contains at least one multiple carbon-carbon bond
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Branched Hydrocarbons
• Contain 1 or more branches off the main chain
8 7 6 5 4 3 2 1
Methyl group on carbon 4
4-methyl-ocatane
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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
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SAME…BUT DIFFERENT
2 CARBONS
6 HYDROGENS
1 OXYGEN
ETHANOL
a primary alcohol
DIMETHYL ETHER
C2H5 OH CH3OCH3
• Same – number and type of atoms
• Different – structure and nameHave different physical and chemical properties
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GROUPS
and
COMPOUNDS
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• Functional Group: halogen (group 17 element)• Name: location-halide-carbon chain
• Examples:
1. 2-bromobutane
2. 1,3 - dichloropentane
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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. Methanol2. 2-Propanol
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Types of Alcohols
• Monohydroxy – contain 1 –OH group– Primary– Secondary– Tertiary
• Dihydroxy (Diol) – contain 2 –OH groups
• Trihydroxy (Triol) – contain 3 –OH groups
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Primary Alcohols
• Contain 1 –OH group
• -OH group is attached to the end of the chain
• Examples: 1. Ethanol
2. Propanol
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H
SECONDARY ALCOHOL R-C-R
O
H•Contain 1 –OH group
•Carbon that is attached to the –OH group is attached to 2 other carbon atoms
2-Butanol
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R
TERTIARY ALCOHOL R-C-R
O
H
2METHYL,2-BUTANOL
•Contain 1 –OH group
•Carbon attached to the –OH group is attached to three other carbon atoms
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2 -OH groups are present
Example: 1,2 ethanediol
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3 -OH groups are present
Example: 1,2,3 propanetriol
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•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
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ethanal
2 carbons alkane aldehyde
• Functional Group: -CHO• Name: drop the final “e” and add “-al”
Propanal
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Propanone
• Functional Group: -CO-• Name: Hydrocarbon name, drop the final “e”, add
“one”
2-Butanone
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• 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
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• 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
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Ester Examples
• Ethyl Methanoate
• Ethyl Ethanoate
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ethanamine
C2H5NH2
• Functional Group: NH2
• Name the chain, add “amine” to the end
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ButanamidePropanamide
• Functional Group: R-CONH2
• Name: Name the chain, add “amide” to the end
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• Functional Groups: -NH2 and –COOH
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• Just like an alcohol, but –SH instead of –OH
Example: Methyl Thiol (CH3SH)
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SUBSTITUTION
ADDITION
ESTERIFICATION
SAPONIFICATION
POLYMERIZATION
COMBUSTION
FERMENTATION
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Ethane Chlorine
• Something takes the place of something else
• Starts with a saturated hydrocarbon
• 2 reactants, 2 products
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Ehtene Cl2 1,2 Dichloroethane
• Start with an unsaturated hydrocarbon• Break the double (or triple) bond• Add in an atom (or group)• 2 reactants, 1 product
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ORGANIC ACID + ALCOHOL H2SO4 ESTER + WATER
Propanoic Acid
Methanol Methyl Propanoate
H2O
Concentrated H2SO4
acts as a dehydrating agent
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FAT
(glycerol ester)
Strong base(NaOH or KOH)
SOAP glycerol
(trihydroxy alcohol)
1,2,3 propane triol
• Reverse of esterification, carried out in the presence of a base
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GLUCOSE
enzyme
ETHANOL
CARBON DIOXIDE
C6H12 O6 C2H5 OH CO2
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• Hydrocarbon + O2 CO2 + H2O
• Exothermic
Example:
C2H6 + O2
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Poly...poly...poly…poly...poly...polymerization
• Chains of small units make up a MACROMOLECULE
• Examples: Plastics, proteins
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Condensation Condensation PolymerizationPolymerization
• 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
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Addition Addition PolymerizationPolymerization
• Bonding of monomers of unsaturated compounds by “opening” a multiple bond in the carbon chain
• Example: polyethylene and many plastics
n C2H4 (C2H4)n