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17 Cards in this Set
- Front
- Back
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List 7 Reactions to synthesize alcohols |
1. Reaction of alcohols with hydrogen halides |
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PROPERTIES OF:
Reaction of alcohols with hydrogen halides |
Reactivity: 3* > 2* > 1*
Sn1 |
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PROPERTIES OF:
Reaction of alcohols with thionyl chloride |
1* and 2* alcohols
Sn2 |
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PROPERTIES OF:
Reaction of alcohols and phosphorus tribromide |
1* and 2* alcohols
Sn2 |
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PROPERTIES OF:
Acid catalyzed dehydration of alcohols |
E1
3* > 2* > 1* rearrangement possible |
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Why do we convert alcohols to mesylates, tosylates, and triflates
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makes OH a good leaving group
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PROPERTIES OF:
Converting primary alcohols to ethers. (Condensation reaction) |
2 Eq.
Protonation and Substitution pathway |
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PROPERTIES/REAGENTS OF:
Fischer Esterification |
- Reversible reaction
Reagents: 1. Always 1 alcohol & 1 carboxylic acid 2. Acid (H2SO4) |
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PROPERTIES/PRODUCTS OF:
Reaction of alcohols and acyl chlorides |
Removal of proton from alcohol, removal of Cl ion from acyl chloride
Products: 1. Ester formation 2. HCl formation |
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PROPERTIES/PRODUCTS OF:
Reaction of alcohols and acid anhydrides |
Anhydride is cleaved at middle oxygen, acylate part is protonated, other part gets the R-O portion of alcohol
Products: 1. ester formation 2. carboxylic acid also formed |
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REAGENTS FOR:
Oxidation of primary alcohols to carboxylic acids |
K2Cr2O7/K2CrO4/KMnO4
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REAGENTS FOR:
Oxidation of secondary alcohols to ketones |
PDC/PCC
or K2Cr2O7/K2CrO4/KMnO4 |
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REAGENTS FOR :
Oxidation of primary alcohols to aldehydes |
PDC/PCC
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REAGENTS FOR:
Oxidation and Cleavage of Vicinal Diols |
Periodic Acid (HIO4)
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PROPERTIES/PRODUCTS OF:
Oxidation and Cleavage of Vicinal Diols |
Vicinal Diols Only
Can be used to open cyclic diols Cleavage between two OH bearing carbons Carbonyl is formed on each carbon bearing the OH Product: Ketone or Aldehyde, depending on substituents |
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REAGENTS FOR:
Condensation reaction |
H2SO4
(primary alcohol as substrate) |
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Describe an Acid Anhydride
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An organic compound with 2 acyl groups bound to the same oxygen.
(RCO)2--O |
