Chapter 14 Flashcards
(21 cards)
Williamson ether synthesis
ethers are prepared
works on methyl and primary alkyl halides `
Williamson ether synthesis - reagents
NaH
RX
Alkoxymercuration - demurcation
alcohol replaces water to form markovnikov addition of alcohol across alkene
Alkoxymercuration - demurcation - reagents
1) Hg(OAc) ROH
2) NaBH4
Acidic Cleavage
when heated with acid ether will undergo acidic cleavage
Acidic Cleavage - reagents
xs HX
heat
Acidic Cleavage - phenyl ether
when cleaved under acidic conditions, produces a phenol and alkyl halide
Autooxidation
ethers undergo autooxidation in presence of O2 to form hydroperoxides
Autooxidation - reagents
O2
Slow
Ether preparation - reagents
H3O+
preparation with peroxy acids
alkenes are converted into epoxides upon treatment with peroxy acids
preparation with peroxy acids - reagents
RCO3H or
MCPBA
Preparation from halohydrins
alkenes can be converted to halohydrins with treated with halogen
Preparation from halohydrins - reagents
Br2
H2O
NaOH
Epoxide to alkene
Br2
H2O
NaOH
Ring opening reactions of epoxide - base - reagents
NaOH
H2O
Acid catalysed ring opening - primary and secondary
primary is attacked
Acid catalysed ring opening - primary and tertiary
tertiary is attacked
Acid catalysed ring opening - reagents
H3O+
Grignard reagent - ketone or aldehyde
aldehyde or ketone will appear of first carbon
grignard reagent - epoxide
C=O is on second carbon
