CHAPTER 12: ALCHOLS AND PHENOLS REACTION

STARTING MATERIAL: ROH

REAGENTS:base and Na* + Sn2

REACTION: Preparation of Alkoxides

PRODUCTS:R-O-Na

STARTING MATERIAL: aldehyde

REAGENTS:

h2, high pressure, pd/pt/ni

or

NaBh4, MeOH

or

1. LiAlH4

2. H2O

REACTION: aldehyde reduction

PRODUCTS: alcohol attached to R group and two hydrogens

STARTING MATERIAL: ketone

REAGENTS:

h2, high pressure, pd/pt/ni

or

NaBh4, MeOH

or

1. LiAlH4

2. H2O

REACTION: Ketone Reduction

PRODUCTS: alcohol attached to R group and two hydrogens

STARTING MATERIAL: ester

REAGENTS:

1. LiAlH4

2. H2O

REACTION: Reduction of Ester

PRODUCTS: two hydrogens and one hydroxyl group

STARTING MATERIAL: carboxylic acid

REAGENTS: LiAlH2

REACTION: carboxylic acid reduction

PRODUCTS: two hydrogens and one hydroxyl group

STARTING MATERIAL: R-Br

REAGENTS: Mg, Ether

REACTION:Production of Gignard Reagents

PRODUCTS: H-MgBr

STARTING MATERIAL: Ketone/Aldehyde

REAGENTS:

1. H-MgBr

2. H2O

REACTION:Grignard Reaction with a Ketone or Aldehyde

PRODUCTS:

Ketone: 3 degree alcohol

Aldehyde: 2 degree alcohol

STARTING MATERIAL: Ester

REAGENTS:

1. H-MgBr

2. H2O

REACTION: Grignard Reaction with an Ester

PRODUCTS: Tertiary alcohol

STARTING MATERIAL: R-OH

REAGENTS: TMS-Cl, pyr

REACTION: Silyl Protection of an Alcohol

PRODUCTS: R-O-TMS

STARTING MATERIAL: R-O-TMS

REAGENTS: H3O+ or TBAF

REACTION: De-protection of TMS

PRODUCTS: R-OH

STARTING MATERIAL: Tertiary alcohol

REAGENTS: HX

REACTION: Sn1 of alcohol

PRODUCTS: tertiary halide

STARTING MATERIAL: Primary and secondary alcohols

REAGENTS:

HBr

OR

1. TsCl, pyr

2. NaBr

OR

PBr3

REACTION: Sn2 of alcohols

PRODUCTS: inversion of stereochemistry to form halides

STARTING MATERIAL: Primary and Secondary Alcohols

REAGENTS: SOCl2, Et3N

REACTION: Sn2 Reaction

PRODUCTS: inversion of steriochemistry with Cl replacement

STARTING MATERIAL: tertiary alcohol

REAGENTS: heat, H2SO4

REACTION: E1 of Alcohols

PRODUCTS:

STARTING MATERIAL: tertiary alcohol

REAGENTS:

1. TsCl, pyr

2. base

REACTION: E2 of Alcohol

PRODUCTS:

STARTING MATERIAL: primary alcohol

REAGENTS:

PCC

or

DMP

or

1. DMSO

2. Et2N

REACTION: alcohol oxidation

PRODUCTS: Aldehydes

STARTING MATERIAL: primary alcohols

REAGENTS: H2CrO4

REACTION: Oxidation of alcohols

PRODUCTS: carboxylic acid

STARTING MATERIAL: Secondary Alcohol

REAGENTS:

H2CrO4

or

PCC

or

DMP

or

1. DMSO

2. Et2N

REACTION: Oxidation of secondary alcohols

PRODUCTS: Ketone