arenes and aromaticity

Cumene

benzene + isopropyl

naphthalene

2 benzene rings

anthracene

3 benzene rings (straight)

phenanthrene

3 benzene rings (off)

bond length of alkane

150

bond length of alkene

130

bond length of whole benzne

~140

structure of a benzene

• electrons are not localized

• circle in a ring stands for resonance

• possesses aromacity

frost circle

• wherever polygon touches circle, there is an energy level

halobenzene (ex. bromo benzene)

benzene with a halogen substituent

tertbutyl benzene

benzene connected to tertbutyl group

nitrobenzene

benzene connected to nitro group

toulene

benzene connected to methyl group

methoxcy benzene/anisole

ether with a benzene

benzoic acid

benzene with carboxylic acid

benzaldehyde

benzene with aldehyde

acetophenone

benzene with a ketone

benzophenone

2 benzenes connected with ketone

phenol

benzene with alcohol

aniline

benzene with NH2

styrene

benzene with a alkene

naming

• substituents in alphabetical order

• lowest numbers possible

ortho

1,2

meta

1,3

para

1,4

physical properties of arenes

• nonpolar

• insoluble in water

• less dense than water

• carcinogenic

• reactions occur at side chain or at ring

LUMO

lowest occupied molecular orbital

HOMO

highest occupied molecular orbital