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. <IMAGE>

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

b. <IMAGE>

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

a. CH₃CH₂CH₂OH

b. <IMAGE>

c. <IMAGE>

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. <IMAGE>

b. <IMAGE>

Name the following compounds:

a. <IMAGE>

b. <IMAGE>

c. <IMAGE>

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

a. CH₃CH₂CH₂SH

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

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). <IMAGE>

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

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

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. <IMAGE>

b. <IMAGE>

c. <IMAGE>

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. <IMAGE>

b. <IMAGE>

c. <IMAGE>

What is the structural relationship between a thiol and an alcohol?

Oxidation of a dithiol such as 2,5-hexanedithiol forms a six-membered ring containing a disulfide group as part of the ring. Draw the structure of this cyclic disulfide (Hint: Draw the starting compound in line structure format first). <IMAGE>

Write the formulas and IUPAC names for the following common alcohols (Hint: See Table 14.1).

a. Rubbing alcohol

Write the formulas and IUPAC names for the following common alcohols (Hint: See Table 14.1).

d. Diol used as antifreeze (two answers)

Name the following compounds:

c. <IMAGE>

d. <IMAGE>

'Designer vinegars' have become very popular over the past decade. Vinegars made from champagne, merlot, and other wines are but a few of these. All wines contain ethanol, and these vinegars are simply wines containing microorganisms that have caused oxidation of the ethanol present. If vinegar is simply ethanol that has been oxidized, what is the structure of the acid formed?

Draw all possible cyclic C₇H₁₄O alcohol isomers having a cyclohexane ring and a methyl group. (Hint: Adapt the method described in Worked Example 12.12 to arrive at your answers.)

Using the alcohol shown, draw all the possible alkenes that might be formed on its dehydration. Which do you think will be the major product(s)? Which do you think will be the minor product(s)? It is alright to have more than one major and minor product. <IMAGE>

Using the alcohol shown, draw all the possible alkenes that might be formed on its dehydration. Which alkenes can exist as cis–trans isomers? Draw them, in both condensed and line structure, and identify each as cis or trans. Explain your choices. <IMAGE>

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

CH₃CH=CHCOOH

Draw the structural formulas of the following compounds:

2-Methoxy-2-methylpropane