Organic Reagents

Alkene
HX

Eliminate Double
Add X on Most Sub

Carbo-X
Li

Carbo-Li
LiX

Carbo-X
Mg

Carbo-Mg-X

Alkane
X2
Light

Add X on Most Sub

Carbo-X
OH

Carbo-OH
X

Carbo-TS
CN

Carb-CN
TS

Carbo-X
Carbo-Li

Carbo-Carbo
LiX

SH
N(Carbo)4

Carbo-SH
N(Carbo)3

CN
Carbo-X

Carbo-CN with Inverted Stereo

X-Carbo-OH
H-

Internal Sub to Make Oxirane

Carbo-O-Carbo
HX

Carbo-X
X-Carbo
H2O

Oxirane
HX
H2O

X-Carbo-X with X on neighbors to O

Carbo-X
"Nitroane"

Add Carbo to N in "Nitroane"

Carbo-OH
HX

Carbo-X
H2O

Carbo-OH
PX3

Carbo-X
OH-PX2

Carbo-OH
SOX2

Carbo-X
SO2
HX

Carbo-OH
P(Ph)3
CX4

Carbo-X with Inverted Stereo
HCX3
O-P(Ph)3

Carbo-OH
TSX
"Nitroane"

Carbo-OTS with Same Stereo
H-"Nitroane"
X

P(Ph)3
Carbo-X

Carbo-P(Ph)3

Carbo-X
H2O
Heat

Carbo-OH
HX

Alkene-X
H2O
Heat

Alkene-OH in Racemic Mix
H3O+

Carbo-X
H2O
CN
Heat

Carbo-CN

Cycloalkane-X
H2O
Heat

Cycloalkane-OH in Racemic Mix

Carbo-X
Carbo-OH
Heat

Carbo-O-Carbo
Alkene in Racemic Mix
Carbo-OH2

S-Carbo-S
X-Carbo-X

Carbo Joined by S in Ring

Cyclo(2)alkene-X
Heat
Carbo-OH

Benzene
Carbo-OH2

Carbo-OH
H3O+
Heat
CH2Cl2

Alkene
H2O

Cyclo(1)alkene-OH
H3O+

Cyclo(2)alkene

Anti-periplanar Carbo-X
Carbo-O

Alkene

Carbo-X
O(Me)3
DMSO

Most Sub Alkene

Benzene-X
:NH2

Benzene

Ketone-O-Carbo-H
Heat

Ketone-OH
Carbo becomes Alkene

Cycloalkane-NO(Me)2
Heat

Cyclo(1)alkene
OH-N(Me)2

Carbo-N(Me)3
O(Me)3
DMSO

Least Sub Alkene
N(Me)3

Carbo-X
Carbo-OH
N(Me)3

Carbo-N(Me)3

X-Alkene-OH
Heat
(Me)3OH

Oxirane-Alkene
HX

Alkene
H-OTS
Benzene

More Sub Alkene

Alkene
H2O
H3O+

Markvonikov Hydration
Carbocation Rearrangement
Alkane-OH

Carbo-OH
HOTS

Alkene Mix

Diene
HX

Carbocation with Best Resonance
X-Alkene

Carbo-O-Alkene
HX

Carbo-O-Alkane-X

Ring-Alkene
HX

Ring Expansion
Ring-X

Alkene
BH3
THF
H2O2
KOH

Anti-Markovnikov Hydration
Carbo-OH

Alkene
X2

X-Carbo-X

Alkene
Peracid

Stereospecific
Epoxide
Carboxyl

Alkene
H2
Pd

Alkane

Carbo-OH
H-
THF

Carbo-O

Cyclo(1)alkene
X2
CX4

X have opposite stereo
Cycloalkane-X2

Cyclo(1)alkene
X2
H2O

X and OH have opposite stereo
X-Cycloalkane-OH

X-Carbo-OH
H-
Carbo-O-Carbo

Epoxide from internal

Alkene-Carbo-OH
X2
CX4

X-Oxirane from internal
HX

Cyclo(1)alkene
X2
Carbo-OH

X and O-Carbo have opposite stereo
X-Cycloalkane-O-Carbo

Alkene
Hg(OAc)2
H2O
-BH4

No carbocation Rearrangement
Markovnikov Addition
Alkane-OH

Bicyclic Alkene
H3O+
H2O

Exo Face Attack
Bicylic-OH

Bicyclic Alkene
Hg(OAc)2
H2O
-BH4

Endo Face Attack
Bicyclic-OH

Alkene
Carbo-OH
Hg(OAc)2
-BH4

Alkane-O-Carbo

Alkene
MCPBA
CH2Cl2

Epoxide
Insoluble MCPBA Byproduct

Bicyclic Alkene
MCPBA

Exo Face Attack
Bicyclic-Epoxide
Insoluble MCPBA Byproduct

X-Bicyclic-OH
H-

Endo Face Attack
Bicyclic-Epoxide

Carbo-Epoxide
CN

O and CN have opposite stereo
O-Carbo-CN

Carbo-Alkene-H
Carbo-Li

Carbo-Alkene:

Carbo-Alkene:
Epoxide
H2O

Carbo-Alkene-Unfolded_Epoxide-OH

Epoxide
Cu(Carbo)2

O and Carbo have opposite stereo
Unfolded Epoxide-Carbo

Epoxide
LAH
THF

Unfolded Epoxide
Attacks Least Sub

Epoxide
N3
DMF

Attacks Least Sub
N3-Unfolded Epoxide-OH

N3-Carbo-OH
LAH OR H2/Pd

H2N-Carbo-OH

Epoxide
OH
H2O

Attacks Least Sub
OH-Unfolded_Epoxide_OH

Epoxide
H3O+
H2O

Attacks Most Sub
Backside Attack
OH have opposite stereo
OH-Unfolded_Epoxide-OH

OH-Cycloalkane-O-Carbo
H-
Carbo-X

Carbo-O-Cycloalkane-OH
Trade places

X-Cycloalkane-OH
H-

Cycloalkane-Epoxide

Cyclo(1)alkene
MnO4
CH3OH
H2O

Cycloalkane-(OH)2
OH have same stereo

Cyclo(1)alkene
OsO4

Cycloalkane-(OH)2
OH have same stereo

Alkene
O3
Zn OR S(Me)2

Split double bond down middle
Carbo-O, O-Carbo

Alkene
CH3OH
O3

Ketone
HO2-Alkane-OCH3

Cyclo(1)alkene
O3
S(Me)2

Unfolded Cyclo with 2 Double_Bond Oxygen

Alkene-NO
Alkene

1,3 dipole addition
Cyclo-NOane+Alkane

Alkyne-NO
Alkene

Cyclo-NOene

Alkyne-NO
Alkyne

Cyclo-NO(2)ene

N2-Carbo
Alkene

Cyclo-N2ane

N3-Carbo
Cycloalkene

Cyclo-N3-Carbo-Cycloalkane

Alkene
N2-Carbo
Heat/Light

Cyclopropane

Cycloalkene
HCX3
O(Me)3

Cycloalkane-Cycloprane-X2

Trans Alkene
Zn
Carbo-X2

Carbo-Cyclopropane

Bicyclic alkene
H2
Pd

Attack Less Incumbered Face
Bicyclic Alkane

Alkyne
2 equiv. HX

X on same carbon
Alkane-X2

Alkyne
2 equiv. X2

Alkane-X4
X2 on each carbon of former triple bond

Carbo-alkyne
(Cy)2BH OR 9BBN
KOOH

Anti-markovnikov hydration
Carbo-carboxyl

Alkyne
Hg(OAc)2
H3O+
H2O

Markovnikov Hydration Carbonyl

Alkyne
Lindlar Catalyst
Pd/BaSO4/Pb

Cis Alkene

Alkyne
Na OR Li
NH3

Trans Alkene

Benzene
1 equiv. CH3OH
NaNH3

Cyclo(2)alkene

Alkene
H-X
Radical Initiator
Heat/Light

Alkane-X

Diene
H-X
Radical Initiator
Heat/Light

5-Exo
Cycloalkane-X

Carbo-alkene
CX4
Radical Initiator
Heat/Light

Carbo-X-CX3
X on most sub carbon of double
CX3 on least sub carbon of double

Cycloalkane-X
SnH(Me)3
Radical Initiator
Heat/Light

Cycloalkane
SnX(Me)3

Cycloalkane-X-Alkene
SnH(Me)3
AIBN

5-Exo
Cycloalkane-Cycloalkane

X-Carbo-Alkene
SnH(Me)3
AIBN

If gonna form cyclopropane, it will unfold back to double bond
H-Carbo-Alkene

Carbo-X
AIBN
SnH(Me)3

Radical Shifts Aren't a Thing
Carbo-H

CH4
X2
Heat/Light

CH3-X
H-X
Br is most selective of more sub

Cyclo(1)alkene
X2
Light

X-Cyclo(1)alkene