14-2

Question 1

Williamson ether synthesis steps
R-OH
1:
2:

Answer 1

1: Alcohol is deprotonated to give an alkoxide (nucleophile) ion (Na or NaH)
2: Introduce an electrophile (R’-X) and SN2 will give R-O-R’ for an ether

Question 2

Alkoxide ion formula

Answer 2

R-O(-) (six free electrons)

Question 3

SN2 restrictions

Answer 3

1: The subtraste (electrophile) must be a methyl or primary halide because secondary halides are less efficient.
2: Only occur at sp^3 (tetrahedral) hybridized centers, not at sp^2.

Question 4

Ether cleavage method

Answer 4

excess acid and heat

Question 5

ether cleavage products

R-O-R

Answer 5

R-X+X-R+H2O

Question 6

Ether synthesis for alcohols:

Ether synthesis for Alkenes:

Answer 6

Ether synthesis for alcohols: Williamson ether

Ether synthesis for Alkenes: MCPBA