Ch.17 Aromatic Compounds

-cyclic

-resonance

-conjugated

-4n + 2pi electrons (Huckel's rule)

-coplanar

aromatic requirements

antiaromatic

contain 4n electrons (4,8,12,etc)

weak base- N has resonance

strong base- N doesn't participate in resonance

How do you know if nitrogen in a weak or strong base in an aromatic compound?

toluene

phenol

anisole

aniline

benzoic acid

benzaldehyde

acetophenone

styrene

ortho (o)

next to each other

para (p)

opposite side

meta (m)

two groups separated by a carbon

heterocyclic

ring shaped carbon chain which has to have at least one atom that isn't carbon in the ring

pyrrole

pyridine

furan

thiophene

oxidation

oxidation 2nd reagent

substitution SN1

substitution SN2

free radical bromination

elimination E1

elimination E2

or:

DBU

tbuOK

catalytic hydrogenation

must have high temp + pressure because aromatics are very stable

birch reduction

hydrogen, oxygen

oxygen, hydrogen

reduction gains ____________ and loses ________________

oxidation gains ______________ and loses ____________

benzylic position

any carbon atom attached directly to a benzene ring (must have at least 1 hydrogen)

ortho and para are more stable then meta

which is more stable: ortho, para, or meta?

sp3

NBS can only react on carbons that are _______

birch reduction mechanism

electron donating group (EDG)

An atom or group that release electron density to neighboring atoms from itself

toluene, phenol, anisole, aniline

EDG examples

electron withdrawing group (EWG)

a group or atom that has the ability to draw electron density toward itself and away from other adjacent atoms

benzoic acid, benzaldehyde, acetophenone

EWG examples

halogen

Aromatic substitution cannot take place if there's a ___________ attached

PCC