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• Oxidation is always coupled with reduction.

• Loss of electrons is oxidation.

• ain of electrons is reduction.

• !he oxidation state of a car"on ato# e$uals the total  nu#"er of its %&O, %&', and %&( "onds.

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• *eduction at car"on increases the nu#"er of %&+ "onds or

decreases the nu#"er of %&O, %&', or %&( "onds.

• Oxidation at car"on decreases the nu#"er of %&+ "onds orincreases the nu#"er of %&O, %&', or %&( "onds.

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+ydro-en, sodiu# "orohydride, and hydraine are the

reducin- a-ents/

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ro#ine and chro#ic acid are the oxidiin- a-ents/

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+2 as a *educin- 3-ent

#2$ Pd on charcoal %a or &i metal in

li' %#(

%aB#) or &iAl#)

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*eduction "y %atalytic +ydro-enation

 3ddition of two hydro-en ato#s/

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Only the al6ene su"stituted to "enene is reduced/

*eduction of car"on7nitro-en dou"le and triple "onds/

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*eduction of 9etones and 3ldehydes

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*osen#und *eduction

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:issol;in-

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*eduction "y 3ddition of

a +ydride Ion and a Proton

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 3ldehydes, 6etones, and acyl halides can "e reduced to

alcohols "y sodiu# "orohydrides/

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Li3l+ is a stron-er reducin- a-ent than 'a+

Li3l+ is used to reduce co#pounds that are

unreacti;e toward 'a+

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:I3L+ allows the addition of one e$ui;alent of hydride

to an ester/

*eplacin- so#e of the hydro-ens of Li3l+ with 7O*

-roups decreases the reacti;ity of the #etal hydride/

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>or#ation of 3#ines "y *eduction

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'a+ can "e used to selecti;ely reduce an aldehyde or 

a 6eto -roup in a co#pound/

3l6enes and al6ynes do not possess a partial positi;e

char-e/

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?odiu# "orohydride can "e used as a che#oselecti;e

reducin- a-ent/

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Oxidation of 3lcohols

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Oxidation of a Pri#ary 3lcohol

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=echanis# of 3lcohol Oxidation

"y the ?wern Oxidation

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Oxidation of 3ldehydes and 9etones

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!he !ollens rea-ent oxidies only aldehydes/ 

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oth aldehydes and 6etones can "e oxidied "y

peroxyacid/ the aeyer7@illi-er oxidation

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=echanis# of the

aeyer7@illi-er Oxidation

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Predictin- aeyer7@illi-er reaction products/

% t lli ?t h i t

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%ontrollin- ?tereoche#istry

in ?ynthesis

3n enantioselecti;e reaction for#s #ore of oneenantio#er than of another/

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+ydroxylation of 3l6enes

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=echanis# for cis-lycol >or#ation

+i-her yields of the diol are o"tained with os#iu#

tetroxide than with per#a-anate

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Oxidati;e %lea;a-e of 1,2

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?u##ary of 3l6ene +ydroxylation *eactions

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Per#a-anate %lea;a-e of 3l6enes

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Exa#ples of per#a-anate

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Oxidati;e %lea;a-e of 3l6enes "y

Oonolysis

Exa#ples/

?tructure of Oone

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?tructure of Oone

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!he al6ene and oone under-o a concerted six

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Oonides can "e clea;ed to car"onyl co#pounds/

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Oonolysis =echanis#

1

Exa#ples of the Oxidati;e %lea;a-e of

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Exa#ples of the Oxidati;e %lea;a-e of

 3l6enes "y Oonolysis

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!he "enene rin- is not oxidied under #ild oonolysis

conditions/

Oxidati;e %lea;a-e of 3l6ynes

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Oxidati;e %lea;a-e of 3l6ynes

!he sa#e rea-ents that oxidie al6enes also oxidie

al6ynes/

:esi-nin- a ?ynthesis "y >unctional

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:esi-nin- a ?ynthesis "y >unctional

roup Intercon;ersion

%on;ersion of an aldehyde to other functional -roups/

%on;ersion of a 9etone into

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%on;ersion of a 9etone into

an Ester or an 3lcohol