Ethers have some slight solubility in water. Explain this using the concept of hydrogen bonding.

Rank the following according to boiling point, highest to lowest:

a. CH₃CH₂CH₂OH

b. CH₃CH₂(OH)CH₂OH

c. CH₃CH₂CH₃

d. CH₂(OH)CH(OH)CH₂OH

For each of the following molecules, (i) redraw using line structure format, (ii) identify its hydrophobic and hydrophilic parts, and (iii) predict its solubility in water.

c.

What alkenes might be formed by dehydration of the following alcohols? If more than one product is possible in a given case, indicate which is major.

b.

What alcohols yield the following alkenes as the major product on dehydration?

b.

What products would you expect from oxidation of the following alcohols?

a. CH₃CH₂CH₂OH

b.

c.

From what alcohols might the following carbonyl-containing products have been made (red = O, reddish-brown = Br)?

(a) <IMAGE>

(b) <IMAGE> 

Draw structures for the following:

a. 2,4-Dinitrophenol

b. m-Ethylphenol

Name the following compounds:

a.

b.

Name the following compounds:

a.

b.

c.

What disulfides would you obtain from oxidation of the following thiols?

a. CH₃CH₂CH₂SH

b. 3-Methyl-1-butanethiol (skunk scent)

Give systematic names for the following alkyl halides:

a.

b.

2-Aminopropane is an achiral molecule, but 2-aminobutane is chiral. Explain.

Which of the following molecules are chiral? (Hint: Draw each molecule and analyze it as illustrated in Worked Example 14.2.)

a. 3-Chloropentane

b. 2-Chloropentane

c.

Predict the product of the following reaction:

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The compound pictured here is a thiol. (a) Draw its line structure, and (b) draw the structure of the disulfide formed when it is treated with an oxidizing agent (yellow = S).

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Draw structures corresponding to the following names:

a. 2,4-Dimethyl-2-heptanol

Draw structures corresponding to the following names:

b. 2,2-Diethylcyclohexanol

Draw structures corresponding to the following names:

f. 3,3-Dimethyl-1,6-heptanediol

Draw structures corresponding to the following names:

c. Phenyl tert-butyl ether

Draw structures corresponding to the following names:

e. 2,4-Dimethoxy-3-methylpentane

Draw structures corresponding to the following names:

f. 3-Methoxy-4-methyl-1-pentene

Identify each alcohol named in Problem 14.32 as primary, secondary, or tertiary.

a.

b.

c.

d.

e.

f.

Arrange the following 6-carbon compounds in order of their expected boiling points, and explain your ranking:

a. Hexane

b. 1-Hexanol

c. Dipropyl ether (CH₃CH₂CH₂—O—CH₂CH₂CH₃)

Draw the structures of the aldehydes that might be oxidized to yield the following carboxylic acids:

c. CH₃CH=CHCOOH

What type of product is formed on reaction of an alcohol with Na metal?

Assume that you have samples of the following two compounds, both with formula C₇H₈O. Both compounds dissolve in ether, but only one of the two dissolves in aqueous NaOH. How could you use this information to distinguish between them?

Which of the following alcohols can undergo oxidation? Draw the line structure of the product expected for those that can. Assume an excess of oxidizing agent is present.

a.

b.

c.

The following alkenes can be prepared by dehydration of an appropriate alcohol. Show the structure of the alcohol in each case that would provide the alkene shown as the major product.

e. 1,4-Pentadiene

What alcohols would you oxidize to obtain the following carbonyl compounds?

a.

b.

c.