CH 12 Flashcards
what acts as nuc for metal hydride reduction
H-
metal hydride reducing agents
NaBH4 or LiAlH4 / H2So4 or H20
NaBH4 reduces aldehydes to?
primary alc
NaBH4 reduces ketones to?
secondary alc
What do NaBH4 not react with?
carboxylic acids, esters, amides
borohydride reduction reagent
NaBH4, protic solvent
which reducing agent is more reactive
LiAlH4
what are LiAlH4 incompatible with?
protic solvents
LiAlH4 reduces aldehydes to?
primary alcs
LiAlH4 reduces carboxylic acids to?
primary alcs
LiAlH4 reduces esters to?
primary alcs
LiAlH4 reduces ketones to?
secondary alcs
what is the product of metal reduction on esters
2 alcs
what is the product of metal reduction on carboxylic acids
alc + H20
can u add Mg to a halide with an alpha sp2 center to turn it into a grignard
yes
what solvent to use with grignard
nonprotic
what do grignards react with
carbonyls
when do grignards act twice
when there is a LG
Grignard rule: look for tertiary alc, if have 2 of same alkyl group probably a grignard added twice to an ?
ester
grignard rule: if tertiary alc has 3 diff groups, grignard addition to unsymmetrical ?
ketone
Grignard rule: secondary alcs come from gignards and a ?
aldehyde
what don’t grignards react with
carboxylic acids
reagent for grignard rxn
1)RMgBr
2)H20 or H2SO4
what funct groups need protection
OH
what to use to subst for alc via SN2
SOCl2,pyr or PBr3
what is a williamson ether synthesis
SN2 rxn w/ alc and primary halide
secondary alcs are oxidized to?
ketones
primary alcs are oxidized to?
aldehyde or carboxylic acid
do tertiary alcs get oxidized
no
chromic acid oxidizes primary alcs to ? in ? conditions
carboxylic acids, aqueous conditions
PCC and PDC selectively produce ? from ? and are done in?
aldehydes, primary alcs, anhydrous organic solvents
what does swern ox do
oxidizes primary alc to aldehydes without metal reagents
reagent for PCC/PDC
PCC or PDC / DCM
reagent for chromic acid ox
Na2Cr2O7 or K2Cr2O7/ H2SO4, H20
reagent for swern
1)DMSO, (COCl)2, DCM / 2)Et3N
for mech of ox, when to react aldehyde to go to carboxylic acid?
when in aqueous` conditions
what does DMP do
oxidizes primary alcs to aldehydes and secondary alcs to ketones
