PHENOLS, ETHERS and EPOXIDES

1. Write equations for each of the following reactions:

a)

b)

c)

2,6-dichlorophenol + Br₂ =

2. Which phenol in each of the following pairs is more acidic:

a) 2,4,6-trimethylphenol or 2,4,6-trinitrophenol

b) 2,6-dichlorophenol or 3,5-dichlorophenol

c) 3-nitrophenol or 4-nitrophenol

3. Identify the principal organic products:

a)

b)

c)

d)

4. Write the structure of each of these ethers.

1. chloromethyl methyl ether

2. 2-(chloromethyl) oxirane

3. 3,4-epoxy-1-butene (2-vinyloxirane)

5. Predict the products

a)

b)

c)

d)

e)

6. Select reaction conditions that would allow you to carry out each of the following transformations:

a)

b)

7. Suggest short reaction sequences suitable for preparing following compounds from the given starting materials:

a) 1-phenyl-2-propanol from bromobenzene and isopropanol

b) 1-methoxy-2-propanol from propylene oxide and methanol

c) 2-methoxy-1-propanol from propylene oxide and methanol

8. What is the principal organic product formed in the reaction of ethylene oxide with each of the following:

1. sodium cyanide (NaCN)

2. NaOH

3. 1-butyn sodium

4. sodium amide

5. sodium methoxide

6. NaI

9. A series of dialkyl ethers was allowed to react with excess hydrogen bromide with the following results. Identify the ether in each case.

1. one ether gave a mixture of bromocyclopentane and 1-bromobutane

2. another ether gave only benzyl bromide

3. phenol and methyl bromide were obtained

4. 1,5-dibromopentane

10. When (+)-2-phenyl-2-butanol is allowed to stand in methanol containing a few drops of sulfuric acid, racemic 2-methoxy-2-phenylbutane is formed. Suggest a reasonable mechanism for this reaction.

11. Suggest short, efficient reaction sequences suitable for preparing each of the following compounds from the given starting materials and any necessary organic or inorganic reagents:

1

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