solutions to problems ethers, building bridges to knowledge

1

Solutions to Problems Ethers

Building Bridges to Knowledge

Photo of the Delicate Arch in Arches National Park near Moab, Utah 1. Write structural formulas for:

(a) 1,2-epoxyhexane

(b) diisopropyl ether

2

(c) diallyl ether

(d) dibenzyl ether

2. Write names for the following compounds

(a)

di-4-methylpentyl ether or diisohexyl ether (b)

4-ethoxyphenyl phenyl ether or p-ethoxyphenyl phenyl ether (c)

3

benzyl vinyl ether (d)

isobutyl 3,3-dimethylbutyl ether or 3,3-dimethylbutyl 2-methylpropyl ether

3. The proton magnetic spectrum and carbon thirteen magnetic spectrum of an unknown compound, C8H8O, are illustrated below.

4

When HBr is added to C8H8O, C8H8Br2 is obtained. The proton magnetic spectrum and carbon thirteen magnetic spectrum of C8H8Br2 are illustrated below.

5

Suggest structures for C8H8O and C8H8Br2.

C8H8O

C8H8Br2 4. Compounds A and B can be formed via the following reaction.

Compounds A and B react with lithium methide followed by acid hydrolysis to produce compounds C and D. Compound A and B react with dilute hydrochloric acid to produce compounds E and F. Suggest structures for compounds A, B, C, D, and E.

6

7

8

5. Suggest a mechanism for the following conversion.

(1)

9

(2)

(3)

(4)

(5)

10

(6)

6. Suggest products from the following reactions

(a)

(b)

(c)

11

7. Suggest a synthesis for the following from the indicated starting material and any other necessary organic or inorganic materials.

+ NaBr

12

8. Suggest a synthesis for the following, from the indicated starting material and any other necessary organic or inorganic materials.

R isomer The objective is to synthesize the isomer with the R designation. The reaction sequence will give the racemic mixture, but the racemates are resolvable.

13

The S isomer

The R isomer

14

9. Suggest products for the following reactions.

(a)

(b)

(c)

10. Suggest a synthesis for the following molecule from the

indicated starting materials and any other necessary organic or inorganic materials.

15

11. Suggest a synthesis for the following molecules using an analogous format you used to synthesis the ether in problem 10.

12. If the following proton magnetic spectrum represents the

product of problem 10, sketch the H1 NMR spectrum for the product of problem 11.

16

13. Suggest mechanisms (a series of elementary steps) to rationalize the following observations: (a)

17

(1)

(2)

(b)

(1)

(2)

18

(3)