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 hydrocarbonCnH2n+2

ONE TRIPLE bond between two Carbons

Unsaturated Hydrocarbon

ONE DOUBLE bond between two Carbons

Unsaturated hydrocarbonCnH2n

CnH2n-2ALKYNES...

ALKENES...Family Name

…counting the CARBONSPREFIXES

ALKANES

• Contain all single bonds

• Naming: carbon prefix + -ane

Examples:

Octane

Butane

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

8 7 6 5 4 3 2 1

Methyl group on carbon 4

4-methyl-ocatane

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

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

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. Methanol2. 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 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

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

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

ethanal

2 carbons alkane aldehyde

• Functional Group: -CHO• Name: drop the final “e” and add “-al”

Propanal

Propanone

• Functional Group: -CO-• Name: Hydrocarbon name, drop the final “e”, add

“one”

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

ethanamine

C2H5NH2

• Functional Group: NH2

• Name the chain, add “amine” to the end

ButanamidePropanamide

• Functional Group: R-CONH2

• Name: Name the chain, add “amide” to the end

• 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

Ethane Chlorine

• Something takes the place of something else

• Starts with a saturated hydrocarbon

• 2 reactants, 2 products

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

ORGANIC ACID + ALCOHOL H2SO4 ESTER + WATER

Propanoic Acid

Methanol Methyl Propanoate

H2O

Concentrated H2SO4

acts as a dehydrating agent

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

GLUCOSE

enzyme

ETHANOL

CARBON DIOXIDE

C6H12 O6 C2H5 OH CO2

• Hydrocarbon + O2 CO2 + H2O

• Exothermic

Example:

C2H6 + O2

Poly...poly...poly…poly...poly...polymerization

• Chains of small units make up a MACROMOLECULE

• Examples: Plastics, proteins

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

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