Professional Documents
Culture Documents
Aldehyde&Ketone
Aldehyde&Ketone
1)
2)
3)
4)
1)
(carbonyl group)
+ C O
C=O
(RCHO)
(RCOR)
CH3
O
O
H
H3C
Cinnamaldehyde
CH2
Carvone
CH3
CHO
H
HO
OCH3
Vanillin
H3C
CH3
Citral
H3C
CH3
CH3
CH3
Muscone
Camphor
H3C
CH3
OH
CH3
CH3
CH3
Testosterone
Progesterone
(oC)
56
-7.0 C
0.04 g/100
58
56.5 C
infinite
CH3CH2CH2CH=CH2
70
30.0 C
0.03 g/100
CH3CH2CH2CH=O
72
76.0 C
7 g/100
96
103.0 C
insoluble
98
155.6 C
5 g/100
(CH3)2C=CH2
(CH3)2C=O
CH2
2)
2.1) ( IUPAC)
al
1
O
H
O
H
Methanal
( HCHO )
CH3
Ethanal
OH
1 H
Butanal
O
H
4-Hydroxybutanal
CH3
CH3
H3C CH CH2
O
CH CH
CH2CH3
2.2) ()
aldehyde
O
O
O
OH
OH
Formic acid
Acetic acid
O
H
OH
H3C
O
H
Formaldehyde
H3C
Br
Acetaldehyde
Br
CHO
carbaldehyde
CHO
CHO
2-cyclopentenecarbaldehyde
2.3) ( IUPAC)
-one
O
H3C
O
CH3
Propanone
CH3
C CH CH3
CH3
3-methyl-2-butanone
O
CH3
C CH CH2OH
CH3
4-hydroxy-3-methyl-2-butanone
H3C
CH2 CH2 C
CH3
O
C
CH2
CH3
(cyclic ketones)
1
O
O
1
4
2
3
Br
3-bromocyclohexanone
O
O
CH3
H3C
H3C
CH3
Br
CH3
2.4) ()
ketone
O
H3C
H3C
CH3
Dimethyl ketone
O
CH3
CH2CH3
CH3CH C CH CH3
C CH CH3
CH3
Br
CH3
IUPAC
O
CH3
C CH3
CH3
acetone
benzophenone
acetophenone
CH3
HO
CH3
CH CH2
C H
CH3
COOH
CH3
CH3
CH CH2
C H
3-methyl-4-oxopentanal
CHO
3-formylbenzoic acid
O
HC
CCH
Propynal
(6S)-chloro-3-hepten-2-one
O
O
H
3-cyclobutyl-3-oxopropanal
1.
O
O
O
OH
H
O
H
A. (E)-4-Methyl-4-hexenal
B. 2-Hydroxybutanal
C. 3-Hydroxybutanal
D. 4-Octyn-3-one
E. 4-Octyn-6-one
F. 2-Cyclohexenone
2.
3-Hexaone
3-Methyl-3-butenal
4-Hexen-2-one
4-Chloro-2-pentanone
2,4-Hexanedione
Butanedial
3-Methylbutanal
4-Methyl-3-penten-2-one
Phenylacetaldehyde
3-Phenyl-2-propenal
3)
1. 1o 2o
2. Friedel-Crafts acylation
Acid chloride/AlCl3 + benzene
ketone
+
4. (Ozonolysis) alkene
R'
H
C
R
C
R''
1) O3
2) (CH3)2S
CH3
R'
H
C O
+ O C
1). O3
2). Me2S
R''
5. (Acylchlorides)
Cl
LiAlH(O Bu)3
O2N
O2N
Cl
CH3
2 O2N
+ (CH3)2CuLi
O
2 O2N
O
Acidic Proton
H
C
R
C
C
Electrophile
()
Nucleophile
()
4.1) ,
4.2)
4.3) - (-Carbon)
4.1) ,
4.1.1) (
)
4.1.2) (hydride)
4.2)
HO
(hydroxide ion)
HOH (water)
(hydride ion)
ROH (alcohol)
R3C (carbanion)
RO
(alkoxide ion)
NC
(cyanide ion)
H3N (ammonia)
RNH2 (amine)
(Hydration)
O
H
HO
+ H2O
H
OH
C
H
(OH-)
1o carbocation
R'
2o carbocation
O -
O -
C +
C +
H
Aldehyde
R'
Ketone
(Steric Hindrance)
Keq
Keq
(Acetal Formation)
(H+)
(, ROH)
(hemiacetal)
(acetal)
(reversible)
(hemiacetal)
O
+ OH
H+
OH
+
OH
HO
HOCH3
HO
OCH3
+
HOCH3
OCH3
+
+ H2OCH3
(acetal)
(hemiacetal)
HO
OCH3
+
HO
H
OCH3
OCH3
+
H+
+ HOH
HOCH3
OCH3
HOCH3
+
CH3O
H
OCH3
CH3O
OCH3
Cyclic Acetals
(diols)
CH2 CH2
O
O
O
+
CH2
HO
CH2
OH
H+
-H2O
H+
-H2O
hemiacetals
acetals
(Cyanohydrin Formation)
O
CH3CH2
HO
CH3
+ HCN
CH3CH2
CN
C
CH3
KCN(aq)
C O
CN -
room
temperature
H+
H+(aq)
C
H
OH
C
CN
CN
HCN
NaCN KCN
formaldehyde > aldehydes >
ketones >> ketones
(Primary Amines)/ (NH3)
C=O C=N-R
CH3
H3C
RNH2
C O
Ph
CH3
N C OH
H
Ph
R
_
C
H2N
O
+ Ph
CH3
N C OH
H
Ph
CH3
N C
Ph
(, Imine)
(Imines)
(Secondary Amines) (enamines)
(Enamines)
3.
1.
2.
3.
4.
5.
6.
A.
E.
acetal
oxime
enamine
cyanohydrin
Cyclic hemiacetal
(Intermediate) imime
B.
C.
F.
D.
G.
H.
Organometallic Reagents
(Alcohol Formation)
/Grignard Reagent
organic halides
/Grignard Reagent
1
2
4.
(Deoxygenation)
C=O CH2
:
Clemmensen
Wolff-Kishner
Clemmensen
O
C
CH2CH3
Zn(Hg)
CH2CH2CH3
HCl, H2O
O
CH2
Zn(Hg)
H
HCl, H2O
CH2
CH3
Clemmensen
Wolff-Kishner
CH2
C H
H2N NH2
CH2
C H
NNH2
KOH
heat
CH2
CH3
Wittig
ylides betaine
phosphine phosphine
oxide
+
+
Ph3P
Ph3P
H3C
C O
CHCH3
Ph
+
Ph3P
_
O
C CH3
CH3 Ph
H C
Ph3P
C CH3
CH3 Ph
C CH3
CH3 Ph
H C
Ph3P
H
H C
H3C
O
C
CH3
Ph
Wittig
4.3) - (-Carbon)
KetoEnol Tautomerism
tautomerism
tautomerism
(-Elimination)
Iodoform Test
-methyl
NaOI
NaOH
I2
NaOI
HI
(Sodium
Hypoiodite)
H
R
C
OH
CH3 + NaOI
C
O
5.
1-Phenylethanol Benzene Ethanol
?
MgBr
CH3CH2OH
H
C
O
H3C
OH
H
CH3
6.