Orgo Exam 2 (17,18,19)

Toluene

Phenol

Anisole

Aniline

Benzoic Acid

Benzaldehyde

Acetophenone

Styrene

Xylene (Ortho)

chromic acid reacting with alkylbenzene 

potassium permanganate (KMnO4), which must then be treated with a proton source in order to obtain benzoic acid.

free-radical bromination also occurs readily at benzylic positions

benzylic halides undergo SN1 reactions rapidly

Benzylic halides also undergo SN2 reactions very rapidly

E1 reaction of benzylic halide

E2 reaction of benzylic halide

Bromination of Benzene

Bromination of Benzene

Chlorination of Benzene 

Fuming H2SO4

Sulfonation of Benzene

the reaction between benzene and SO3 is highly sensitive to the concentrations of the reagents and is, therefore, reversible

Nitration 

This method can be used to install a nitro group on an aromatic ring. Once on the ring, the nitro group can be reduced to give an amino group (NH2).

This process provides us with a general method for installing an amino group on a benzene ring. First, a nitro group is installed on the ring (nitration), and then the nitro group is reduced to an amino group

Friedel–Crafts Alkylation

Friedel–Crafts Acylation

Clemmensen reduction

Blocking Group

Sulfonation is commonly used for this purpose, because the sulfonation process is reversible.

Bromination

Br2, FeBr3/AlBr3

Chlorination

Cl2, AlCl3

Iodination

I2, CuCl2

Nitration

HNO3, H2SO4

Sulfonation

Fuming H2SO4

Friedel-Crafts Alkylation

CH3(R)Cl, AlCl3

Friedal-Crafts Acylation

Cl-O=-R,AlCl3

Reduction (NO2 to NH2)

1)Fe or Zn, HCl 2)NaOH

Benzylic Bromination (CH3 to CBr3)

Excess NBS

Oxidation (CH3 to -=O-OH)

1) KMnO4, H2O,Heat 2) H3O+

Clemmensen Reduction(Just alkane)

Zn(Hg),HCl heat