Use LEFT and RIGHT arrow keys to navigate between flashcards;
Use UP and DOWN arrow keys to flip the card;
H to show hint;
A reads text to speech;
17 Cards in this Set
- Front
- Back
List 7 Reactions
|
1. Reaction of alcohols with hydrogen halides
2. Reaction of alcohols with thionyl chloride 3. Reaction of alcohols and phosphorus tribromide 4. Acid catalyzed dehydration of alcohols 5. Conversion of alcohols to mesylates, tosylates, and triflates 6. Converting primary alcohols to ethers. (Condensation reaction) 7. Fischer Esterification |
|
PROPERTIES OF:
Reaction of alcohols with hydrogen halides |
Reactivity: 3* > 2* > 1*
Sn1 |
|
PROPERTIES OF:
Reaction of alcohols with thionyl chloride |
1* and 2* alcohols
Sn2 |
|
PROPERTIES OF:
Reaction of alcohols and phosphorus tribromide |
1* and 2* alcohols
Sn2 |
|
PROPERTIES OF:
Acid catalyzed dehydration of alcohols |
E1
3* > 2* > 1* rearrangement possible |
|
Why do we convert alcohols to mesylates, tosylates, and triflates
|
makes OH a good leaving group
|
|
PROPERTIES OF:
Converting primary alcohols to ethers. (Condensation reaction) |
2 Eq.
Protonation and Substitution pathway |
|
PROPERTIES/REAGENTS OF:
Fischer Esterification |
- Reversible reaction
Reagents: 1. Always 1 alcohol & 1 carboxylic acid 2. Acid (H2SO4) |
|
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 |
|
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 |
|
REAGENTS FOR:
Oxidation of primary alcohols to carboxylic acids |
K2Cr2O7/K2CrO4/KMnO4
|
|
REAGENTS FOR:
Oxidation of secondary alcohols to ketones |
PDC/PCC
or K2Cr2O7/K2CrO4/KMnO4 |
|
REAGENTS FOR :
Oxidation of primary alcohols to aldehydes |
PDC/PCC
|
|
REAGENTS FOR:
Oxidation and Cleavage of Vicinal Diols |
Periodic Acid (HIO4)
|
|
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 |
|
REAGENTS FOR:
Condensation reaction |
H2SO4
(primary alcohol as substrate) |
|
Describe an Acid Anhydride
|
An organic compound with 2 acyl groups bound to the same oxygen.
(RCO)2--O |