Beruflich Dokumente
Kultur Dokumente
Chapter 16
Synthesis of Aldehydes
1. Oxidation of
1o
Alcohols
Synthesis of Aldehydes
2. Reduction of Carboxylic Acid Derivatives
t Mechanism:
l Step 1: hydride transfer to carbonyl forms sp3 intermediate
l Similar mechanism
Synthesis of Ketones
ketones
Initial anion cannot add a second alkyl group
tetrahedral
OM
R1
R1
Nuc
Nuc
H
t
R2
Acetals
t An aldehyde (or ketone) in excess alcohol and an acid catalyst
hemiacetal
Thioacetals
t Thioacetals can be formed by reaction of an aldehyde or
Formation of Imines
Enamines
t Secondary amines cannot form a neutral imine by loss of a
Georg Wittig
The Nobel Prize in Chemistry 1979
t Aldehydes and ketones react with
oxide
l The driving force for the last reaction is formation of the strong
Empty d orbitals on P
help stabilize carbanion
Example:
The -hydroxyester is
easily dehydrated to an
a,-unsaturated ester
MCPBA
O
O
13
C NMR Spectra
l 1 H NMR Spectra
Aldehyde protons give sharp signals at 9-12
The aldehyde proton often shows coupling to the protons on the -carbon
Protons on the carbon generally appear at 2.0-2.3