Ch 14 Reactions

Question 1

Alcohol (Primary, Secondary, or Tertiary) –> Ether

Answer 1

SN1 with alkyl halide

Question 2

Alkyl Halide (Primary or Secondary) –> Ether

Answer 2

Alkoxide to do SN2

Question 3

Alkene –> Ether

Answer 3

1) Hg(OAc)2, R-OH 2) NaBH4

Question 4

Ether –> 2 Alkyl halides + H2O

Answer 4

2 eq HBr or HI (NOT HCl)

Question 5

Thiol (Primary, Secondary, or Tertiary) –> Thioether

Answer 5

1) R-SH + NaH 2) Alkyl Halide

Question 6

Thiol (Primary, Secondary, or Tertiary) –> Sulfonium Ion

Answer 6

1) Creation of thioether 2) Alkylation

Question 7

Alkene –> Epoxide

Answer 7

mCPBA or other peroxyacid in CCl4 or CH2Cl4

Question 8

Alkene –> Epoxide

Answer 8

1) X2, H2O 2) NaOH

Question 9

Epoxide –> Alcohol on least substituted carbon

Answer 9

Base-catalyzed epoxide opening

Question 10

Epoxide –> Alcohol on most substituted carbon

Answer 10

Acid-catalyzed epoxide opening