organic chemistry the study of carbon-containing compounds and their properties. the vast majority...

Organic ChemistryOrganic Chemistry

The study of carbon-containing compounds and their properties.

The vast majority of organic compounds contain chains or rings of carbon atoms.

22_502

H

H

H H

H

H

CC

22_501

H1s

sp2

sp2

sp2

sp2

H1s

2p

C C

sp2

sp2

22_504

2p

2pH1s

H

sp

2p

2p

C

sp 2p

2p

2p

C H

H1s

2p

sp

BondsBonds

HydrocarbonsHydrocarbons

. . . compounds composed of carbon and hydrogen.

Saturated: carbon-carbon bonds are all single - alkanes [CnH2n+2]

H C

H

H

C

H

H

H

HydrocarbonsHydrocarbons(continued)(continued)

Unsaturated: contains carbon-carbon multiple bonds.

H C

H

H

C

H

CH

H

Types of HydrocarbonsTypes of Hydrocarbons

Types of HydrocarbonsTypes of Hydrocarbons

Rules for Naming AlkanesRules for Naming Alkanes

1. For alkanes beyond butane, add -ane to the Greek root for the number of carbons.

C-C-C-C-C-C = hexane

2. Alkyl substituents: drop the -ane and add -yl.

-C2H5 is ethyl

Rules for Naming AlkanesRules for Naming Alkanes

3. Positions of substituent groups are specified by numbering the longest chain sequentially.

C C-C-C-C-C-C

3-methylhexane

4. Location and name are followed by root alkane name. Substituents in alphabetical order and use di-, tri-, etc.

AlkanesAlkanes

HydrocarbonsHydrocarbons

Cyclic AlkanesCyclic Alkanes

Carbon atoms can form rings containing only carbon-carbon single bonds.

C3H6, C4H8, C6H12

22_499

C C

C

109.5

60

No "head-on"overlap of atomic orbitals

(b)(a)

Alkenes and AlkynesAlkenes and Alkynes

Alkenes: hydrocarbons that contain a carbon-carbon double bond. [CnH2n]

CC=C propene

Alkynes: hydrocarbons containing a carbon-carbon triple bond.

CCCCC 2-pentyne

Nomenclature for AlkenesNomenclature for Alkenes

1. Root hydrocarbon name ends in -ene

C2H4 is ethene

2. With more than 3 carbons, double bond is indicated by the lowest numbered carbon atom in the bond.

C=CCC is 1-butene

Aromatic CompoundsAromatic Compounds

Refinery ProcessesRefinery Processes

Cracking: large molecules broken down to smaller ones by breaking carbon-carbon bonds.

Pyrolysis (thermal cracking): The process that produces cracking at high temperatures.

Catalytic Cracking: Cracking at lower temperatures.

Catalytic reforming: Alkanes and cycloalkanes converted to aromatic compounds.

Reactions and Functional GroupsReactions and Functional Groups

A special class of cyclic unsaturated hydrocarbons.

+ Cl2

FeCl3

Cl

+ HCl

benzene Chlorobenzene

The Common Functional The Common Functional GroupsGroups

Class General Formula

Halohydrocarbons RX

Alcohols ROH

Ethers ROR

AldehydesCRO

H

The Common Functional The Common Functional GroupsGroups

Class General Formula

Ketones

Carboxylic Acids

Esters

Amines RNH2

CRO

R'

CRO

OH

CRO

O R'

Functional GroupsFunctional Groups

Functional GroupsFunctional Groups

NamingNaming

NamingNaming

NamingNaming

NamingNaming

NamingNaming

NamingNaming

PolymersPolymers

. . . are large, usually chainlike molecules that are built from small molecules called monomers.

Monomer PolymerEthylene PolyethyleneVinyl chloride Polyvinyl chlorideTetrafluoroethylene Teflon

Types of PolymerizationTypes of Polymerization

Addition Polymerization: monomers “add together” to form the polymer, with no other products. (Teflon)

Condensation Polymerization: A small molecule, such as water, is formed for each extension of the polymer chain. (Nylon)

EnantiomersEnantiomers

END