Chapter 19 Reactions

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Reduction of aldehydes and ketones to alcohols

LiAlH4
or
NaBH4/alcohol
NaBH4 is more selective

Acetal formation

aldehyde or ketone + alcohol
strong acid (trace)

Oxidation of aldehydes

1. KMnO4
2. -OH
or
K2Cr2O7/H3O+

Imine Formation

Aldehyde or Ketone + H2NR
H3O+ (dilute strong acid) or -OH

Enamine Formation

Aldehyde or Ketone + HNR2
H3O+ (dilute strong acid)

Wolff-Kishner Reduction (Carbonyl to methylene)

H2N-NH2
KOH
ethylene glycol (solvent)

Clemmenson Reduction (Carbonyl to methylene)

Zn/Hg/
HCl/H2O

Wittig Alkene Synthesis

Ph3P+(CH2)- (an ylid) + aldehyde or ketone

ylid Preparation (Sn2 reaction)

1. Ph3P + CH3X
2. C4H9Li

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