Orgo 2 Exam 1

hydrohalogenation

mark

hydrohalogenation

hydrohalogenation

hydrohalogenation

hydrohalogenation

diels alder

s-cis

s-trans

diels alder

diels alder

diels alder

endo rule

substituents must be endo while the hydrogens must be exo

bicyclic diels alder

bicyclic diels alder

retro diels alder

electrocyclic

electrocyclic

electrocyclic

4e-

heat trans, light cis

4e-

heat trans, light cis

6e-

heat cis, light trans

6e-

heat cis, light trans

8e-

heat trans, light cis

sigmatropic rearrangement

when symmetrical, 3-3 is formed

sigmatropic rearrangement

sigmatropic rearrangement

allyl vinyl ether

aryl vinyl ether

sigmatropic rearrangement

hydrohalogenation

diels alder

bicyclic diels alder

10 annulene

non-aromatic

14 annulene

aromatic

2 annulene

antiaromatic

6 annulene

aromatic

8 annulene

nonaromatic

12 annulene

antiaromatic

antiaromatic

a ring is ________ if it’s aromatic in every way except it’s number of pi e- is a multiple of 4 (4n; 4, 8, 12, 16..)

aromatic

planar, fully conjugated, delocalized e-, 4n+2 pi e-, all carbons must be sp2 to be planar

ortho

1,2

meta

1,3

para

1,4

priority

aldehyde > ketone > alcohol > amine > alkyl

phenol

aniline

anisole

toluene

benzoic acid

benzaldehyde

o-xylene

m-xylene

p-xylene

acetophenone

benzophenone

styrene

oxidation

oxidation

oxidation

free-radical halogenation

substitution

substitution

elimination

ellimination

elimination

birch reduction

birch reduction

halogenation

halogenation

EAS mechanism

E = Cl or Br

B: = FeCl4 or FeBr4

halogenation

selefluor is used

halogenation

nitration

hydrosulfonation

reduction

friedel-craffs alkylation

limitations

1. any alkyl halide can be used (single bonds only)

2. impossible to stop at mono-alkylation (multiple substitutions)

3. wont react if theres a strong deactivator

rearrangement

rearrangement

friedel-acylation

friedel-acylation

sandmeyer

sandmeyer

sandmeyer

rearrangement

friedel acylation

reduction

nh2 to n2+

aromatic rxns

hydrolysis

activating groups

faster rxn, lone pair e- directly connected to benzene, neg or partial neg charge

ortho/para director

deactivating groups

slower rxn, pos or partiall pos charge

meta director

exception: halogens ortho/para deactivators

halogenation

sulfonation and halogenation

chlorination

sulfonation

ring priority

bromination

bromination

NAS (nucleophilic aromatic substitution)

NAS