Reagent/Catalyst of Alcohols/Ether/Epoxide/ Phenols/Thiol/ Sulfides

AE Hydration Alkene/Alkynes

H20/H2SO4

SN Reactions Haloalkanes

H2O

Carbonyl Reduction

Aldehyde/Ketone

NaBH4, ethanol or water/ Weak acid (H3O+)

Carbonyl Reduction

Carboxylic Acid/ Ester

LiAlH4, ether/ Weak acid (H3O+)

Grignards Reaction RMgX

Carbonyl Groups

RMgX, ether/ Weak acid (H3O+)

Grignards Reaction RMgX

Carbonyl Groups; Ester

2RMgX, ether/ H3O+

E1 Dehydration of Alcohol

Secondary & Tertiary Alcohol

H2SO4/ H2O

Oxidation of Alcohol

Primary & Secondary Alcohol

CrO3/NaCr2O7/KMnO4

Periodinane/ DCM

SN2 Williamson’s Ether Rxn

NaX & RX

AE Alkenes

ROH/ H+

Peroxy Acids (mCPBA)

Acidic Ether Cleavage

HX (HBr or I)

Epoxide

HX

H3O+

Dow Process

Benzene

NaOH,H2O/35Odeg & H+

NaOH/H2O & NaOH/350deg & H+

Oxidation-Reduction

Phenols

Na2Cr2O7/ H3O & SnCl2, H2O

Oxidation-Reduction

Hydroquinone

Na2Cr2O7/H3O

SN1

Primary & Secondary Haloalkanes

Thiol ion (-SH)

SN 1

RSH (Oxidation)

RSH, I2 or Br2

SN1

Disulfides

Zn in CH3COOH

SN2 Sulfide Synthesis

Thiol

NaH & RI