Products

Ozonolysis Partial Mechanism

O

O

O O

O

O O

O

O O

O

O

Ozone contributing structures

O

O

O

H

H

H3C

H3C

Malozonide

Rearrangementin two steps

2. (CH3)2S

Ozonide

(Chemist opensup flask)

1. O3

2. (CH3)2S

Example:

Summary:

Regiochemistry:

Stereochemistry:

Breaks c

i EMakemga s

pa

pbondy

c ifbad HEE c'ofHE

Replaced C with 2 GOO Aldehyde11 O11

Eet i iReaction of an alkene with Oz creates

an ozonide intermediate that decomposeswith the addition of cuts zS Aldehydes

ketonesN ANIAI 3

z

Ajit

This is the only reactor thatbreaks C bond

1 re0

2 CADI NIH HRH2

Elf a yet'ts 6 2 CHIS

Hydrogenation: H2 with Pt°, Pd°, Ni°

H H H H

CC

H3C

H

H

H

H H H H

H H HH H

Products

H H H H

Pt°, Pd°, Ni° metal particle surfaceH

HH

H

H2 / Pd°

Example:

Summary:

Regiochemistry:

Stereochemistry:

Converts alleges to alkanese overallreduction

c

00001 it

If it'IE Ea'tv I lveryfast

Hs4 HHAE Est very 1134if fast HHoof itI

H 1

Hz adsorbs onto the metal surfaceAlkene adsorbs onto the metal surfaceIt atoms transfer both C atoms onthe same face before the C C band rotatesN Asyn addition

Et naplaneof If'Eta

chiralsymmetry

ra H MPd

r is t

EE Eis EI.EE ETeEiiEasRace n is

Alkynes the two orthogonal1T bonds definealkyne reactions

R C C R Same overallpersonality and thereforereactions as alkenes

A Reaction of 2 equivalents of Xzf Ce Br

c Hz CEC HH'c cliff Reactorscan stopBr here

Bra

CHz CBR CH Br

Vicinal tetra halide