Chapter 17

What do we mean by the expression functional group?

Explain how halogenated hydrocarbons are named.

Explain how hydrocarbons containing an \(\mathrm{NH}_{2}\) group are named.

Explain how hydrocarbons containing an OH group are named.

Explain how hydrocarbons containing an OH group are named.

Why is chlorine an important functional group?

Why have Freons been banned?

What class of compounds does the general formula \(\mathrm{R}-\mathrm{OH}\) represent? What does the \(\mathrm{R}\) represent?

How can you convert \(\mathrm{R}-\mathrm{Cl}\) to \(\mathrm{R}-\mathrm{OH}\) ?

A student claims there are three isomers of propanol: 1-propanol, 2-propanol, and 3-propanol. Is he correct? Explain.

Draw all the isomers of the alcohols having the molecular formula \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\).

Wood alcohol is toxic to humans but not to horses. Explain why, and also explain why wood alcohol poisoning in humans is treated by having the patient consume ethanol.

A functional group you did not learn about is called an acid chloride, shown below. Notice how the amine reacts with it. Give a reason or reasons for why the nitrogen atom of the amine seeks out the carbonyl atom of the acid chloride and can form a bond to it.

2-Propanol is quite soluble in water, but 2 -decanol is insoluble in water. Draw both structural formulas and explain why one compound is soluble but the other isn't.

Draw the structural formula of butyl propyl ether and give its molecular formula.

Give the common name and line drawing for ethanoic acid.

Write the equilibrium reaction associated with molecules of the type \(\mathrm{R}-\mathrm{COOH}\). To which side does the equilibrium lie? What does this imply?

Radioactivity is often called ionizing radiation. Why?

Show how a carboxylic acid, \(\mathrm{R}-\mathrm{COOH}\), reacts with a tertiary amine, \(\mathrm{NR}_{3}\).

Write an equilibrium to show how a primary amine, \(\mathrm{H}_{2} \mathrm{NR}\), makes water basic. To which side does the equilibrium lie? What does this imply?

Diethylamine is a secondary amine having the formula \(\mathrm{C}_{4} \mathrm{H}_{11} \mathrm{~N}\). Draw a dot diagram for this compound.

Draw the structural formulas for 1-chloropropane, 1-propanol, 1-aminopropane, 2-propanone, propanoic acid, and propanal. Then label each molecule indicating the type of functionalized hydrocarbon it is (alcohol, ketone, aldehyde, and so on).

Consider acetic acid. (a) Draw a dot diagram for it and point out which hydrogen atom is acidic. (b) Why is only the \(\mathrm{H}\) on the oxygen atom acidic? (c) Where are you likely to run across acetic acid outside a chemistry laboratory.

What classes of molecules contain a carbonyl, \(\mathrm{C}=\mathrm{O} ?\)

Hydrocarbons are insoluble in water, but some alcohols, such as methanol, \(\mathrm{CH}_{3} \mathrm{OH}\), dissolve readily in water. Why?

A solution of methyl alcohol in water does not conduct electricity. Why not?

Which do you expect to be most water-soluble: (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{3}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) Explain your answer.

There are three isomers that have the molecular formula \(\mathrm{C}_{5} \mathrm{H}_{12}\). Draw the structural formula for each one. Which do you expect to have the lowest boiling point? Explain.

There are four isomers that have the molecular formula \(\mathrm{C}_{4} \mathrm{H}_{9}\) Br. Draw the structural formula for each one. Name each compound using IUPAC rules.

For each pair of molecules, indicate whether the two are identical, isomers, or completely unrelated.

Using the molecular formula \(\mathrm{C}_{2} \mathrm{H}_{4} \mathrm{Cl}_{2}\), draw the structural formula of (a) a molecule that is polar and \((\mathrm{b})\) a molecule that is nonpolar.

Using the molecular formula \(\mathrm{C}_{4} \mathrm{H}_{6} \mathrm{Cl}_{2}\), draw the structural formula of (a) a molecule that is polar, (b) a molecule that is nonpolar, and (c) a molecule that contains only \(\mathrm{C}-\mathrm{C}\) single bonds.

Benzene is a hydrocarbon that has the molecular formula \(\mathrm{C}_{6} \mathrm{H}_{6}\). The benzene molecule contains a six-carbon ring and three double bonds. Draw its structural formula.

Name all the functional groups possible for molecules that have the molecular formulas (a) \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\) (b) \(\mathrm{C}_{4} \mathrm{H}_{8} \mathrm{O}\), (c) \(\mathrm{C}_{4} \mathrm{H}_{8} \mathrm{O}_{2} .\) Draw a structural formula for each functionalized hydrocarbon.

An organic compound has the formula \(\mathrm{C}_{6} \mathrm{H}_{6}\) and it possesses three \(\mathrm{C}=\mathrm{C}\) double bonds. Draw it.