Synthesis of epoxides

Reactions of epoxides
Reactions of epoxides
 Ex.

HCH3C CH2 HI
CH3CHICH3
propene 2 - iodopropane ( isopropyl halides)

Br
H3C C CH3 Markovnikov addition.
no peroxides
H
2 - bromopropane
HBr
HCH3C CH2 (Isopropyl bromide)

peroxides CH3CH2CH2Br anti - Markovnikov addition.

1 - bromopropane
(n - propyl bromide)
 6. Halohydrin formation

C C + X2 + H2O C C + HX X2 = Cl 2, Br 2
H OH

Ex.

Cl 2, H2O
HCH 3C CH 2 H3C CH CH 2 follow Markovnikov rule
propylene HO Cl
(propene)
propylene chlorohydrin
Hydroxylation. Glycol formation

C C + KMnO 4 or HCO 2OH C C

OH OH
Example.
cold, dil. KMnO or HCO 2OH
HCH 3C CH 2
4
H3C CH CH 2 + 2MnO 2
propylene OH OH
1,2 - propanediol (propylene glycol)

Oxidizing agents that bring about hydroxylation

a. cold alkaline potassium permanganate, KMnO4
b. peroxy acids, such as peroxyformic acid HCO2OH
 Ozonolysis (Cleavege reaction)

O3 H2O, Zn
CH 3CH 2CH=CH 2 CH 3CH 2CHO + CH 2=O

CH3 H3C H
O3
H3C C=CH 2
H2O, Zn
H3C C=O + O CH

Cleavage – a reaction in which the double bond is

completely broken and the alkene molecules
converted into 2 smaller molecule.