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Electrophilic substitution
H3O+
Hydride reduction with aldehydes
1)NaBH4 and ethanol (EtOH) 2)H3O+ OR use 1)LiAl4 and THF 3)H3O+
Organometallic synthesis
1)LiX and diethyl-ether(Et2O) 2)H3O+
Grignard Synthesis
1)RMgX and THF 2)H3O+
Protection of OH group
Me3SiCl + triethyl-amine (Et3N) (Pterodactyl molecule)
Conversion 1
Alkyl sulfinate and pyr
Conversion 2
PX3 or PX5 and diethyl-ether
Conversion 3
SOX2 and Pyr
Dehydration
H2SO4 and heat
ROH to Aldehyde 1
Pcc and CH2Cl2
ROH to Aldehyde 2
1)DMSO and COCl2
2)triethyl-amine (Pterodactyl)
ROH to Aldehyde 3
DMP and CH2Cl2
ROH to carboxylic acid
CrO3 and H2SO4 and Acetone and H2O
1,2 diolcleavage
HIO4 and H20
Oxidation of a secondary alcohol
pcc chcl2