导图社区 Important reactions
Important reactions思维导图,包括:Reduction、Grignard addition、Dehydration、hydration、Protection、oxidation。
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topic
Important alcohol reactions
Reduction
Products
Alcohols
treatment
1. NaBH4 or LiAlH4
2. H3O+
3. nucleophile could view as a hyride ion H:-
1' alcohol
by reactants
Aldehydes
nucleophilic addition
Carboxylic acids
nucleophilic acyl substitution
Esters
produce also R'OH
ester: RCOOR'
ethers
cleavage by HX, H2O
SN2 when 1'/2' ether
SN1 or E1 when 3' ether
2' alcohol
Ketones
aldehyde
reactant
ester
diisobutylaluminum hydride: DIBAH
Grignard addition
Treatment
1. R'MgBr, ether
3. neucleophile could view as R3C:-
by reactant
formaldehyde
aldehydes
3' alcohol
produce also R''OH
ester: RCOOR''
Dehydration
products
C=CR2
trearment
H3O+
E2
C=C
POCl3
Pyridine
hydration
nucleophilic addition of H2O
always reveriable by elimination/ dehydration
Gemdiol/hydrate(1,1-diol)
%99.9 diols their aqueous solution equilibrium
Subtopic
Catalysis
Acid catalysis
protonation of Carbonyl oxygen makes the carbonyl carbon more electrophilic
Base catalysis
hydroxide ion is more nucleophilic than water
Protection
alcohol protection
-OH+Cl-SiR3(TMS)
form R'-O-SiR3
SN2 like mechanism
Inpresence of a base
removed by aquwous acids with fluoride ion
Ketone/ Aldehydes protection
Acetyl formation
Oxidation
Dess-Martin periodinane
CH2Cl2
mechanism
E2 like
ketones
Carboxylic acid
form hydrate intermediate
p 569
CrO3
could also be KMnO4 and hot HNO3
H3O+, acetone
quinones
phenols
(KSO3)2NO
H2O
Radical