CHEM 2211 Organic Chemistry I:

Chapter 8 Summary of Reactions

Know these!!!!!

Slides 2-7 show the EAS reactions

Slides 8-10 show the side chain reactions

Electrophilic Aromatic substitution (EAS) Reactions

Bromination

Note: All species shown underneath the arrows in these EAS reactions are catalytic in their activity.

Br2

FeBr3

Br

+ HBr

Electrophilic Aromatic substitution (EAS) Reactions

Chlorination

Cl2

FeCl3

Cl

+ HCl

note: AlCl3 may also be used as the catalyst here

Electrophilic Aromatic substitution (EAS) Reactions

Nitration

HNO3

NO2

+ H2OH2SO4

Electrophilic Aromatic substitution (EAS) Reactions

Sulfonation

SO3

SO3H

+ H2OH2SO4

Electrophilic Aromatic substitution (EAS) Reactions

Friedel-Crafts Alkylation

CH3ClCH3

+ HClAlCl3

Electrophilic Aromatic substitution (EAS) Reactions

Friedel-Crafts Alkylation

C

+ HClAlCl3

H3CC

Cl

O

CH3

O

Reduction of aromatic nitro groups

NO2(1) Fe, H3O+

(2) OH-

NH2

Oxidation of alkylbenzene side chains

CH3 CO2H

KMnO4

H2O

Reduction of aromatic alkyl ketones

C

O

CH3 H2 / PdC

H

CH3

H

This is a useful method to place an alkyl group onto a benzene ring withoutthe problems of rearrangement (which could be observed in F/C alkylationreactions).

Other useful infomation• Make sure that you know the directing and activating/deactivating effects of each different group in these reactions (Figure 8.15); This does not mean that you need to memorize this whole table.

• Remember that Friedel-Crafts reactions are somewhat limiting, in that they will not work on a strongly deactivated benzene ring (Figure 8.12); this is of high importance when developing a synthetic procedure.

• Take a look at Table 8.2 for another representation of substituent effects in EAS reactions.