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Carbon-carbon bond forming reactions are indicated by reagents written with solid backgrounds. Reactions that cleave carbon-carbon bonds are
indicated by reagents that are circled.
vicinal tetrahaloalkanes
alkynes
3) S
2
CH
2)(
O
vicinal
dihaloalkanes
r Cat
1) LiAlH4, 2) H2O
(J)
id
ac
alkyl azides
halohydrins
2O
vicinal diols
H O+
3
/H
alkanes
BPA
m-C
i (D
rN
O (B
X 2/H 2
t, o
d, P
(I
3
aN
amines
O
, H 2 , H 2O
Cl 2
1) aOH
N
2)
(I)
/P
H2
R2
NH
(E
R,
NaOR (K)
R
O
Na
haloakanes
NaCN (I)
silyl ethers
ethers
D)
sO 4 (
1) O
HSO 3
2) Na
(I)
HX (A)
SR
nitriles
)
NaC
Na
ROH/acid (J)
thioethers
Ni
alkenes
HO
(I
CR (E
aS
l2 (
L)
OC
.(F)
H2 /Pd, Pt,
thiols
NaO
H(
E)
HO
2 ,a
cid (
J)
X2 (B)
Cl
Si
e3
uM ine
t -B yrid
p
(G)
indla
S(
carboxylic
acids
alcohols
HX
o
rP
Br
or S
NB
H 2/L
Na/NH 3
allylic halides
M)
(
rO 4
H 2C
3,
,
O2
H2
,3 2) D)
BH (C,
1)
OH
Na
)
(A
4
)
H
(A
aB
O
)N
2
2
H
,
+/
O
O
2
,H
H3
2
)
Ac
4
O
PO
g(
H3
H
1)
1)
geminal
dihaloalkanes
aldehydes/ketones
HIO4
(A)
NaNH2/NH3
HX
1)BH 3 NaOH
,
2)H 2O 2
A)
O (
HgS 4
,
O
4
H 2S
PCC (M)
i (E)
RC C L
H2CrO4 (N)
2X
1)(sia)2BH
2)H2O2, NaOH (C)
epoxides
NH3
vicinal
aminoalcohols
Carbon-carbon bond forming reactions are indicated by reagents written in solid backgrounds with white lettering.
a-haloketones
O
O
1)(MeO)2P CH2C OEt
2) Base
a,b-unsaturated esters
Br
2,
imines
ac
ROH/H+
hemiacetals
+
ROH/H
amine,
aldehydes/
ketones
H3O+/H2O
H3O+/H2O
enamines
H
R 2N
RNH2
id
NaBH 3C
1) NaCN
2) H2O
O
3
)H
acetals
,2
Cl
3O +
)H
L, 2
IBA
alkanes
haloalkanes
CH2I2
Zn (Cu)
(R
iAlH
4,
1) Mg
2) CO2
3) H3O+/H2O
1) L
CHX3
(CH3)3COK
uL
i
alkenes
2C
1) 2R
2) H
Ph3P+2CR2
1) D
3O +
, 2) H
2O
/H
HO
2
3 O +/
3O +
H
2)
4,
lH
LiA
1)
MgX
2O
)H
i, 2
uL
2C
R
1)
3) H3O+/H2O
a-hydroxyalkynes
O
,K
H4
N2
1) Mg
O
2)
1) RC CNa
2) H3O+, H2O
H
),
alcohols
2
H2
aB
2
N
,H
1)
Pt
g
(H
1)
O
3
)H
,2
Li
Zn
1)
cyanohydrins
O
3
)H
gX
RM
geminal dihalo
cyclopropanes
vinyl halides
cyclopropanes
carboxylic acids
H
RO
id
s
ba
or
ac
SOCl
O
H2
esters
ROH
acid chlorides
H 2O
N
CH 2
H 2O
H2O
acid
O
H2
d
aci ase
b
or
RCO H
2
RO
NHR
acid anhydrides
NHR2
amides
NHR2
HO
2
acid
o
r ba
se
nitriles
amines
+ H O
/ 2
, 2) H 3O
1) LiAlH 4
1) LiAlH4
2) H3O+/ H2O
amines
R2
R2
R1
R5
R4
R1
O
Nu
R4
O
R3
Nu = enolate forming
species or amines
O
R3
-Alkylated carbonyls
1) R2CuLi
2) H3O+/H2O
Michael
Reaction
Various enolates
or amines
R1
O
R2
R8
R7
R6
R4 R5
Cyclic -Ketoesters
R3
Dieckmann
Condensation
1) NaOEt
HOEt
2) H3O+/H2O
diesters
R3
R3
R4
HO
R1
R1
H3O+
O
R2
-Hydroxy carbonyls
O
R2
-Unsaturated carbonyls
NaOR
HOR
1) LDA
2) R-X
3) H3O+/H2O
R2
Alkylated -carbons
R1
OR4
O
O
-Ketoesters
Enamine
Reactions
1) 2-amine
2) R-X
3) H3O+/H2O
R4
R3
R1
R2 R3
Aldol
Reaction
ketones,
aldehydes
R4
1) 2-amine
2) acid chloride
3) H3O+/H2O
Claisen
Condensation
ester
O
R1
O
R4
R1
HO
R2 R3
-Dicarbonyls
O
HO
O
O
H3C
R1
R2
Alkylated methyl ketones
R1
R2
Alkylated carboxylic acids
R1
H3C
1) NaOEt
HOEt
2) H3O+/H2O
1) NaOEt/HOEt
2) R-X
3) NaOH, H2O
4) H3O+/H2O
5)
Acetoacetic Ester
Synthesis
Malonic Ester
Synthesis
acetoacetic
ester
1) NaOEt/HOEt
2) R-X
3) NaOH, H2O
4) H3O+/H2O
5)
malonic ester
Carbon-carbon bond forming reactions are indicated by reagents written with solid backgrounds and white lettering.
alkene
dienes
cyclohexenes
HX
allylic halides
amines
1) excess Mel
2) NaOH, heat
alkenes
epoxides
1) H2O2
2) heat
1) KN3
2) H2O
3) LiAlH4
4) H3O+/H2O
vicinal amino
alcohols
HNO2
aryl
nitriles
aryl flourides
ketones
aryl iodides
HBF4
KCN
CaCN
quinones
carboxy phenols
1) NaOH
2) CO2
3) H3O+/H2O
KI
aryl diazonium
salts
H2CrO4
1) HNO2
2) HCl
aryl
carboxylic acids
H2O
benzylic bromides
NaOH
H2O
H2CrO4
anilines
H3PO2
phenols
NaNH2
NH3
NBS
alkyl benzenes
halobenzenes
RX
AlX3
H3PO4
R(CO)X
AlX3
acyl benzenes
X2, FeX3
3-ROH
H3PO4
aryl rings
HNO3
H2SO4
H2SO4
SO3
sulfobenzenes
nitrobenzenes
1) Fe
HCl
2) NaOH
H2, Ni