Ethers

sulfuric acid-catalyzed synthesis

2 ethanols + water forms ether and H3O+

• R groups from 2 ethanol bond to oxygen of water

williamson ether synthesis

alkoixde ion + ICH3

• oxygen on cyclopentanol bonds to methyl group

forms ether

silver-oxidized ether formation

alcohol, add CH3I + Ag2O

• CH3 replaces every OH group

forms ether and AgI

alkoxymercuration

alkene to ether

can add…

1. (CF3CO2)2Hg, CH3OH

2. NaBH4

or

1. NaOH

2. CH3CH2Br

• alkene loses double bond or adds to one carbon markonikov to form ether

acidic cleavage

ether to phenol (R’OH) and RX

add HX and H2O

• ether splits at either side of O bond

• oxygen gains H to form OH

• Br adds to other split side

ring-opening

epoxide to diol or halohydrin

H3O+ to have trans 2 x OH addition

HBr + ether to form halohydrin

oxidation (thiol to sulfide)

2 thiols (R-SH) plus Br2/I2

• hydrogen leaves from SH and joins w/X

• form R-S-S-R and 2HX

thiolate reaction

thiolate (RS-) plus R’CH2Br (1/2 halide) to form sulfide

• Na leaves S and CH3 joins

• forms RSCH2R’ + Br-

sulfoxide oxidation

sulfide plus H2O2 and peroxyacid forms sulfone (R2SO2)

• add double-bonded oxygen to S