Chapter 14: Ethers and Epoxides; Thiols and Sulfides

Question 1

12-Crown-4

Answer 1

Li+ Solvation

Question 2

15-Crown-5

Answer 2

Na+ Solvation

Question 3

18-Crown-6

Answer 3

K+ Solvation

Question 4

1)Hg(Oac)2, ROH
2)NaBH4
With alkene

Answer 4

AlkOxyMercuration-Demurcuration
Adds: RO to double bond
MARKOVNIKOV
-using an alcohol instead of water as a reagent produces ethers

Question 5

1) NaH 2)RX

With Alkyl Halide

Answer 5

Williamson Ether Synthesis
Preparing Ethers
-the alkyl halide must be primary

Question 6

Excess H-X, Heat

With Ether

Answer 6

Acidic Cleavge of Ether
Adds: X to each side of the ether
-breaks ether
-O is protented twice and leaves as OH
-Benzene does not have X added, stays as OH

Question 7

O2

With epoxide

Answer 7

Autooxidation

Adds O2 adjacent to epoxide

Question 8

MCPBA

With alkene

Answer 8

Preparation with Peroxy Acids

Adds: epoxide of double bond

Question 9

1) Br2, H2O
2)NaOH
With alkene

Answer 9

Preparation with Halohydrin
Forms epoxide by deprotenating alcohol and SN2 Attack
Cis=cis, trans=trans

Question 10

Nuc, H2O

With ether

Answer 10

Ring-Opening with Strong Nucleophile
Add: Nuc-H to ether
SN2

Question 11

HX

With ether

Answer 11

Acid Catalyzed Ring-Opening 
Adds H to O, and X to carbon
-SN2 Nuc Attack: inversion
-1 and 2: prefers 1 due to sterics
-1 and 3: prefers 3 due to electronics

Question 12

NaOH/H2O, Br2

With 2 Thiols

Answer 12

Oxidation of Thiols

Adds: two thiolate ions together

Question 13

1)NaOH 2)RX

With thiol

Answer 13

Preparing Thioethers
Adds: S to an R group
S is deprotenated, X is LG

Question 14

NaIO4

With sulfide

Answer 14

Oxidize to sulfoxide

Adds double bonded O to S

Question 15

2 eq. H2O2

With Sulfoxide

Answer 15

Oxidize to sulfone

Add two double bonded O to S

Question 16

HCl, Zn

with disulfide

Answer 16

Converts a disulfide bond to two thiols