Williamson Ether Synthesis

Question 1

purpose?

Answer 1

make an ether from RO- + R’-X

Question 2

requires?

Answer 2

good Nu (RO-), also a strong base

good L.G. (Br, I, TsCl) NOT Cl

polar aprotic solvent; ROH if conj. acid of RO-
ex. CH3O- w/ CH3OH as solvent

Question 3

R-X limitations

Answer 3

methyl (CH3X, 1º, sometimes unhindered 2º)

if 3º R-X you get all E2

Question 4

steps

Answer 4

1. ) use strong base to make RO- from ROH (ex. NaH, ether)

2. ) add R-X (ex. CH3Br, ether)

Question 5

if intramolecular

Answer 5

you will see an alkane with an OH on one end and a Br on the other end
(ex. OHCH2CH2CH2CH2Br

makes an ether ring + (Br- Na+)

Question 6

does ring size effect rate for intramolecular?

Answer 6

yes, making smaller rings is faster than making big ones

3~5 > 6

4~7 > 8