Alcohols
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What reagents to create the alcohol?
Top: dilute H2SO4 Middle: 1) Hg(OAc)2, H2O 2) NaBH4 Bottom: 1)BH3 * THF 2) H2O2, NaOH
What reagents to create the alcohol?
NaOH (Sn2)
What reagents to create the alcohol?
H2O
What reagents to create the alcohol?
NaBH4 + a polar aprotic molecule (reduction)
Mechanism for this Reduction Reaction
Products?
butan-2-ol + En.
What reagents to create the alcohol?
1) LiAlH4 2) H3O+ (or any polar aprotic molecule)
Mechanism for this Reduction Reaction
What reagents to create the alcohol?
1) xs LiAlH4 2) H3O+ (LiAlH4 will reduce carboxylic acids and esters, but NaBH4 is not strong enough)
Mechanism for this Reduction Reaction
What reagents to create the alcohol?
Top: 1) LiAlH4 (2 eq.) 2) H3O+ Bottom: 1) NaBH4 (2 eq.) 2) MeOH
What reagents to create the alcohol?
Top: catalytic OsO4, NMO Bottom: 1) RCO3H 2)H3O+
What reagents to create the alcohol?
1) Grignard reagent (RMgX) 2) H3O+ (or H2O)
Mechanism for a Grignard reagent reaction
What reagents to create the alcohol?
1) CH3MgBr 2) H3O+
What reagents to create the alcohol?
1) xs CH3MgBr 2) H3O+
Mechanism for a Grignard reagent and ester reaction
Why is this reaction impossible?
Because the Grignard reagent cannot form when a hydroxyl group in present (it must be protected)
Reagents?
TMSCl, Et3N
Reagents?
H3O+ or F-
Reagents?
First: TMSCl, Et3N Second: 1) Mg 2) RC(=OH)R 3) H3O+ Third: F-
Reagents?
HBr
Reagents?
HCl ZnCl2
Mechanism for OH + Cl reaction
Only for primary. Tertiary will undergo Sn1
