Alcohols: Reactions
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Alcohols: Reactions CH21 PS class
description
Alcohols: Reactions. CH21 PS class. Review your past reactions!. Review your past reactions!. Review your past reactions!. Review your past reactions!. Review your past reactions!. Other ways to synthesize R-OH. Other ways to synthesize R-OH. More reduction…. More reduction…. - PowerPoint PPT Presentation
Transcript of Alcohols: Reactions
Alcohols: Reactions
CH21 PS class
Review your past reactions!
Review your past reactions!
Review your past reactions!
Review your past reactions!
Review your past reactions!
Other ways to synthesize R-OH
Other ways to synthesize R-OH
More reduction…
More reduction…
NaBH4/H3O+ does not really work for esters/ carboxylic acids.
Use LiAlH4 /H3O+ instead.
Practice!
Practice!
Practice!
Practice!
Grignard Reagents + carbonyls
Grignard Reagents + carbonyls
Grignard Reagents + carbonyls
Grignard Reagents + carbonyls
Grignard Reagents + carbonyls
Grignard Reagents + carbonyls
Practice!
Practice
Challenge: USE AN ESTER
Practice
Challenge: USE AN ESTER
Reactions of alcohols: Review SN1/2 E1/E2
Oxidation of R-OH
Acid-dehydration = E1
POCl3 in Pyridine
Practice
Practice
Practice
Practice
Practice
Practice
Oxidation of R-OH
Esters, overview
Oxidation of R-OH
Periodinane is also a viable reagent!
Oxidation of R-OH
Chromate mechanism
Practice
Practice
Practice
More Problems
ProblemsPropose a synthetic route from 2-phenylethanol to make:
AB C D
E
ProblemsPropose a synthetic route from 2-phenylethanol to make:
H2SO4 Pe
riodi
nane
CrO3
KMnO4
1. H2SO4 2. H2/Pd
Problems
Problems
ProblemsGive all Grignard Reagent + Carbonyl pairs to give the ff. alcohols:
A
B
C
D
Problems
A
B
ProblemsGive all Grignard Reagent + Carbonyl pairs to give the ff. alcohols:
A
B
C
D
Problems
C
D
Problems
Problems
Problems
Problems
ProblemsPROPOSE REAGENTS FOR EACH STEP.
ProblemsNaBH4, H3O+
PBr3
1. Convert to Grignard (Mg/ether)
2. add CH2=O then acid
1. Ph-CH2-MgBr 2. 2. H3O+
Periodinane
POCl3 or conc’d H2SO4
