Alcohol Reactions + Preperation Flashcards
What are the four ways to prepare Alcohols?
Substitution, Addition, Reduction of Carbonyl, Grignard Reactions
What are the three additional reactions to prepare Alcohols?
Acid-Catalyzed Hydration, Oxymercuration-Demercuration, Hydroboration-Oxidation
What are the reagents for Acid-Catalyzed Hydration?
H3O+ and H2SO4 as catalyst
What are the reagents of Oxymercuration-Demercuration?
- Hg(OAc)2, H2O
- NaBH4
What are the reagents of Hydroboration-Oxidation?
- BH3 (dot) THF
- H2O2, NaOH
Is Hydroboration Markovnikov or Anti-Markovnikov?
Anti-Markovnikov
Is Oxymercuration Markovnikov or Anti-Markovnikov?
Markovnikov
Is Acid-Catalyzed Hydration Markovnikov or Anti-Markovnikov?
Markovnikov
What are the three agents that can reduce Carbonyls?
- H2 + Pt
- NaBH4 + EtOH/NaOH or H2O
- LiAlH4 + H2O
What is the difference between Catalytic Hydrogenation from the other two reactants?
Catalytic Hydrogenation reduces the carbonyl and an alkene. NaBH4 and LiAlH4 only reduce the carbonyl.
What’s the difference between NaBH4 and LiAlH4?
LiAlH4 (LAH) is strong enough to reduce esters and carboxylic acids *ONLY IF LAH IS IN EXCESS (requires two cycles of the mechanism to fully reduce these groups. NaBH4 is not strong enough. Both create primary alcohols.
What is a Diol?
A compound with two hydroxyl groups. Glycol is synonymous with Diol.
What are the two ways to prepare Diols?
- Reduction of diketones (a compound with two ketones) using previously mentioned reducing agents)
- Anti or Syn Dihydroxylations with an Alkene.
What are Grignard Reagents?
CH3MgBr. These are alkyl halides treated with Mg. This allows carbon atoms to act as an anion. Allows for the addition of Carbon groups and stuff. **CAN ONLY REACT WITH ALDEHYDES, KETONES, ESTERS, EPOXIDES
What is added alongside Grignard Reagents?
H2O so it doesn’t get destroyed.
What are three ways to convert 1st and 2nd-degree alcohols to Alkyl Halides?
- TsCL, py + NaBr
- SOCl2, py
- PBr3
All three cause inversion of stereochemistry.
How do you protect alcohol from Grignards?
The reagent is TMSCl and Et2N. TMS attaches to Oxygen.
How you do remove TMS to bring it back to alcohol?
You use TBAF or H3O+
What is the order of oxidation of Primary Alcohols?
Proceeds to an Aldehyde and then a Carboxylic Acid
What is the order of oxidation of Secondary Alcohols?
Straight to Ketone
What are the oxidizing agents of Alcohols?
Chromic acid for full oxidation. PCC can be used to bring primary alcohol to only an aldehyde
What are the reagents for the oxidation of Alcohols for chromic acid?
- Na2Cr2O7
- H2SO4, H2O
or - CrO3
- H3O+, Acetone
What are the reagents for the oxidation of Alcohols for PCC?
PCC
CH2Cl2 is solvent
What are the alternative reagents for oxidation to create aldehydes from alcohols?
- DMSO, (COCl)2
- Et3N
or - DMP
- CH2Cl2
