CHEM 260 Exam 3

chlorobenzene

ethylbenzene

toluene

phenol

anisole

aniline

benzoic acid

non-planar

non-aromatic

non-planar, no contiguous p orbitals

non-aromatic

planar, non-contiguous p orbitals

non-aromatic

planar, contiguous p orbitals, 4n electrons

anti-aromatic

planar, contiguous p orbitals, 4n+2 electrons

aromatic

cations + aromaticity

donate 0 electrons

anions + aromaticity

donate 2 electrons

Nitrogen/sp2 and aromaticity

donate 1 electron

sp3 heteroatoms and aromaticity

adopt sp2, donate 2 electrons

carbonyl

EWG, meta

-NO₂

EWG, meta

-SO₃H

EWG, meta

-=N

EWG, meta

-CF₃

EWG, meta

-OR

EDG, ortho/para

-NR₂

EDG, ortho/para

alkyl

EDG, ortho/para

halides

EDG, ortho/para

which carbon is the most acidic

alpha carbon

kinetic enolates

more reactive, form faster, away from R

thermodynamic enolates

closer to R, more stable, more substituted

nucleophiles for conjugate addition

R₂CuLi or dicarbonyls

what do cuprates add?

R group

what do dicarbonyls add?

the entire dicarbonyl