Chapter 18 reactions: ethers and epoxides; thiols and sulfides

Synthesis of ether - primary alcohols with acid

R-OH + H30+

Synthesis of ether - Williamson ether synthesis

R-OH —> R-O-R

1. NaH, THF

2. R-X

Synthesis of ether - Silver oxide ether formation

R-OH + R-X/AgO2 —> R-O-R

Synthesis of ether - Alkoxymercuration of alkenes

R=R —> R-R-O-R

1. (CF3CO2)2Hg, R-OH

2. NaBH4

Reaction of ethers - acidic cleavage (also applicable for epoxide opening)

HX

Reaction of ethers - Claisen rearrangement

1. NaH, THF

2. XR=R

Preparation of epoxide - alkene with peroxyacid

mCPBA

Or

RCO3H

Reaction of ethers - Based catalyzed epoxide opening

-OH and H2O

Reaction of ethers - Grignard reagent

MgXR, ether solv./H3O+

Synthesis of thiols (from alkyl halides RCH2X)

1. (H2N)2X=S

2. H2O, NaOH

Oxidation of thiols

X2/Zn, H+

or

X2, H2O

Synthesis of sulfides

1. RX

2. THF

Oxidation of sulfides

1. H2O2

2. mCPBA or RCO3H