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