Alcohols Flashcards
Acid-Catalyzed Hydration
HA, H2O
- Markovnikov addition of H2O with catalytic HA
Oxymercuration-Demercuration
1) Hg(OAc)2, H2O, THF
2) NaBH4
- Markovnikov addition product in which the OH group bonds to the more substituted carbon atom of the alkene.
Sodium Borohydride Reduction
1) NaBH4 2) HA
Aldehydes: Primary Alcohol
Ketones: Secondary Alcohol
Lithium Aluminum Hydride Reduction
1) LiAlH4 (LAH) 2) H2O
Aldehydes: Primary Alcohol
Ketones: Secondary Alcohol
Esters: Two primary alcohols (Needs 2 Eq.)
Carboxylic Acid: Primary Alcohol
Hydroboration
1) BH3:THF, H2O 2) HO-, H2O2
- Converts alkenes into alcohols through a syn, anti-Markovnikov addition
Syn Dihydroxylation
1) OsO4 2) NaHSO3, H2O or
1) KMnO4 2) H2O, OH- cold
- The hydroxyl groups are added to the same face of the alkene, leading to a cis-diol product.
Cleavage of Ethers with HX
HX (X=Cl, Br, and I)
- SN1
Opening of epoxides by a nucleophile (Acidic)
NH3, H2O
- Epoxides can undergo ring-opening with nucleophiles under acidic conditions.
- SN1
Opening of epoxides by a nucleophile (Basic)
NaOCH3, H2O
- Alkoxide or hydroxide ion (strong nucleophile)
Grignard Reaction
R-MgBr, H3O+
- Aldehydes, ketones, and epoxides
Grignard Reaction (Ester)
1) R-MgBr 2) NH4Cl , H3O+
Swerm Oxidation
1) DMSO, (COCl)2 2) Et2N, @ Low Temp.
- Primary Alcohol: Aldehyde
- Secondary Alcohol: Ketone
PCC
PCC (solvent: CH2Cl3)
Jones Reagents
aq. H2CrO4, H2O, Acetone
- Primary Alcohol: Carboxylic Acid
- Secondary Alcohol: Ketones
- Aldehyde: Carboxylic Acid
Phosphorus tribromide
PBr3
- Primary and secondary alcohol reacts with phosphorus tribromide to yield alkyl bromide
Thionyl chloride
SOCl2, Pyridine
Halohydrin
X2, H2O
Acid-Catalyzed Dehydration
H2SO4, H2O
- E1: Secondary and tertiary alcohols
- E2: Primary alcohols
Alcohols with HX
HX
- Acid is required. Acid protonates the alcohol hydroxyl group, making it a good leaving group
