Chapter 22

Classify each of the following hydrocarbons as alkanes, alkenes, or alkynes. (a) \(\mathrm{C}_{6} \mathrm{H}_{14}\) (b) \(\mathrm{C}_{3} \mathrm{H}_{4}\) (c) \(\mathrm{C}_{9} \mathrm{H}_{18}\)

Classify each of the following hydrocarbons as alkanes, alkenes, or alkynes. (a) \(\mathrm{C}_{12} \mathrm{H}_{24}\) (b) \(\mathrm{C}_{7} \mathrm{H}_{12}\) (c) \(\mathrm{C}_{13} \mathrm{H}_{28}\)

Write the formula for (a) an alkene with two carbon atoms. (b) an alkane with 22 hydrogen atoms. (c) an alkyne with three carbon atoms.

Write the formula for (a) an alkyne with 16 hydrogen atoms. (b) an alkene with 44 hydrogen atoms. (c) an alkane with ten carbon atoms.

Write structural formulas for the following alkanes. (a) 3-ethylpentane (b) 2,2-dimethylbutane (c) 2-methyl-3-ethylheptane (d) 2,3-dimethylpentane

Write structural formulas for the following alkanes. (a) \(2,2,4\) -trimethylpentane (b) 2,2 -dimethylpropane (c) 4-isopropyloctane (d) \(2,3,4\) -trimethylheptane

The following names are incorrect; draw a reasonable structure for the alkane and give the proper IUPAC name. (a) 5-isopropyloctane (b) 2 -ethylpropane (c) 1,2 -dimethylpropane

Follow the directions of Problem 9 for the following names. (a) 2, 2-dimethylbutane (b) 4 -methylpentane (c) 2-ethylpropane

Name the following alkenes. (a) \(\mathrm{CH}_{2}=\mathrm{C}-\left(\mathrm{CH}_{3}\right)_{2}\) (b) \(\left(\mathrm{CH}_{3}\right)_{2}-\mathrm{C}=\mathrm{C}-\left(\mathrm{CH}_{3}\right)_{2}\) (c) \(\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}_{2} \mathrm{CH}_{3}\)

Write structural formulas for the following alkynes. (a) 2-pentyne (b) 4-methyl-2-pentyne (c) 2-methyl-3-hexyne (d) 3,3-dimethyl-1-butyne

Classify each of the following as a carboxylic acid, ester, and/or alcohol. (a) \(\mathrm{HO}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{OH}\)

16\. Classify each of the following as a carboxylic acid, ester, and/or alcohol. (a) \(\mathrm{CH}_{3}-\left(\mathrm{CH}_{2}\right)_{3}-\mathrm{OH}\)

In each of the following, name the functional group (i.e., ester, aldehyde, ...). (a) \(\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}_{2}-\mathrm{OH}\)

In each of the following, name the functional group (i.e., ester, aldehyde,....). (a) \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{O}-\mathrm{CH}_{3}\)

Give the structure of (a) a four-carbon straight-chain alcohol with an - OH group not at the end of the chain. (b) a five-carbon straight-chain carboxylic acid. (c) the ester formed when these two compounds react.

Give the structure of (a) a three-carbon alcohol with the -OH group on the center carbon. (b) a four-carbon branched-chain carboxylic acid. (c) the ester formed when these two compounds react.

Write the structural formula of the ester formed by methyl alcohol with (a) formic acid. (b) acetic acid. (c) \(\mathrm{CH}_{3}-\left(\mathrm{CH}_{2}\right)_{6}-\mathrm{COOH}\).

Write the structural formulas of all the esters that can be formed by ethylene glycol with formic and acetic acids. (One or both of the - OH groups of ethylene glycol can react.)

Arrange these compounds in order of increasing boiling point. Values in \({ }^{\circ} \mathrm{C}\) are 0,11 , and 97 . (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{3}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\)

Arrange these compounds in order of increasing boiling point. (a) 1 -butanol, butane, diethylether (b) hexane, 1 -hexanol, dipropylether

The \(K_{\mathrm{b}}\) for ethylamine \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}\right)\) is \(4.3 \times 10^{-4}\). What is the \(\mathrm{pH}\) of a \(0.250 \mathrm{M}\) solution of ethylamine? Compare with the \(\mathrm{pH}\) of a \(0.250 \mathrm{M}\) solution of ammonia \(\left(K_{b}=1.86 \times 10^{-5}\right)\).

When aniline, \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}\left(K_{\mathrm{b}}=7.4 \times 10^{-10}\right)\), reacts with a strong acid, its conjugate acid, \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{3}{\underline{\phantom{xx}}}^{+}\), is formed. Calculate the \(\mathrm{pH}\) of a \(0.100 \mathrm{M}\) solution of \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{3}{\underline{\phantom{xx}}}^{+}\) and compare it with the \(\mathrm{pH}\) of acetic acid \(\left(K_{\mathrm{a}}=\right.\) \(\left.1.86 \times 10^{-5}\right)\)

When ethylamine, a weak base \(\left(K_{\mathrm{b}}=4.3 \times 10^{-4}\right)\), reacts with formic acid, a weak acid \(\left(K_{\mathrm{a}}=1.8 \times 10^{-4}\right)\), the following reaction takes place: \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}(a q)+\mathrm{HCOOH}(a q) \rightleftharpoons \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{3}{\underline{\phantom{xx}}}^{+}(a q)+\mathrm{HCOO}^{-}(a q)\) Calculate \(K\) for this reaction.

When the conjugate acid of aniline, \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{3}{\underline{\phantom{xx}}}^{+}\), reacts with the acetate ion, the following reaction takes place: \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{3}{\underline{\phantom{xx}}}^{+}(a q)+\mathrm{CH}_{3} \mathrm{COO}^{-}(a q) \rightleftharpoons \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}(a q)+\mathrm{CH}_{3} \mathrm{COOH}(a q)\) If \(K_{\mathrm{a}}\) for \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{3}{\underline{\phantom{xx}}}^{+}\) is \(1.35 \times 10^{-5}\) and \(K_{\mathrm{a}}\) for \(\mathrm{CH}_{3} \mathrm{COOH}\) is \(1.86 \times 10^{-5}\) what is \(K\) for the reaction?

Draw the structural isomers of the alkane \(\mathrm{C}_{6} \mathrm{H}_{14} .\)

Draw the structural isomers of the alkene \(\mathrm{C}_{4} \mathrm{H}_{8}\)

Draw the structural isomers of \(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{Cl}\) in which one hydrogen atom of a \(\mathrm{C}_{4} \mathrm{H}_{10}\) molecule has been replaced by chlorine.

Draw the structural isomers of \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{Cl}_{2}\) in which two of the hydrogen atoms of \(\mathrm{C}_{3} \mathrm{H}_{8}\) have been replaced by chlorine atoms.

There are three compounds with the formula \(\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{Cl}_{3}\) in which three of the hydrogen atoms of the benzene molecule have been replaced by chlorine atoms. Draw structures for these compounds.

Write structures for all the structural isomers of double-bonded com- pounds with the molecular formula \(\mathrm{C}_{5} \mathrm{H}_{10}\).

Write structures for all the structural isomers of compounds with the molecular formula \(\mathrm{C}_{4} \mathrm{H}_{6} \mathrm{ClBr}\) in which \(\mathrm{Cl}\) and \(\mathrm{Br}\) are bonded to a doublebonded carbon.

Draw structures for all the alcohols with molecular formula \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\).

Draw structures for all the saturated carboxylic acids with four carbon atoms per molecule.

Maleic acid and fumaric acid are the \(c i s\) - and trans- isomers, respectively, of \(\mathrm{C}_{2} \mathrm{H}_{2}(\mathrm{COOH})_{2}\), a dicarboxylic acid. Draw and label their structures.

R For which of the following is geometric isomerism possible? (a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}=\mathrm{CCl}_{2}\) (b) \(\mathrm{CH}_{3} \mathrm{ClC}=\mathrm{CCH}_{3} \mathrm{Cl}\) (c) \(\mathrm{CH}_{3} \mathrm{BrC}=\mathrm{CCH}_{3} \mathrm{Cl}\)

Which of the following can show optical isomerism? (a) 2-bromo-2-chlorobutane (b) 2 -methylpropane (c) 2,2-dimethyl-1-butanol (d) 2,2,4-trimethylpentane

Which of the following compounds can show optical isomerism? (a) dichloromethane (b) 1,2 -dichloroethane (c) bromochlorofluoromethane (d) 1 -bromoethanol

Classify the following reactions as addition, substitution, elimination, or condensation. (a) \(\mathrm{C}_{2} \mathrm{H}_{2}(g)+\mathrm{HBr}(g) \rightarrow \mathrm{C}_{2} \mathrm{H}_{3} \mathrm{Br}(l)\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}(s)+\mathrm{HNO}_{3}(l) \rightarrow \mathrm{C}_{6} \mathrm{H}_{4}(\mathrm{OH})\left(\mathrm{NO}_{2}\right)(s)+\mathrm{H}_{2} \mathrm{O}(l)\) (c) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}(a q)+\mathrm{HCOOH}(a q) \rightarrow\)

Name the products formed when the following reagents add to 1-butene. (a) \(\mathrm{H}_{2}\) (b) \(\mathrm{Br}_{2}\)

I Name the products obtained when the following reagents add to 2-methyl-2-butene. (a) \(\mathrm{Cl}\) (b) \(\mathrm{I}_{2}\)

Which of the following are expected to show bond angles of \(109.5^{\circ}\) ? \(120^{\circ} ? 180^{\circ} ?\) (a) \(\mathrm{H}_{3} \mathrm{C}-\mathrm{CH}_{3}\) (c) \(\mathrm{H}_{3} \mathrm{C}-\mathrm{C} \equiv \mathrm{C}-\mathrm{CH}_{3}\)

What does the "circle" represent in the structural formula of benzene?

Calculate \(\left[\mathrm{H}^{+}\right]\) and the \(\mathrm{pH}\) of a \(0.10 \mathrm{M}\) solution of chloroacetic acid \(\left(K_{\mathrm{a}}=1.5 \times 10^{-3}\right)\)

Explain what is meant by the following. (a) a saturated fat (b) a soap (c) the "proof \(^{n}\) of an alcoholic beverage (d) denatured alcohol

The general formula of an alkane is \(\mathrm{C}_{n} \mathrm{H}_{2 n+2}\). What is the general formula of an (a) alkene? (b) alkyne? (c) alcohol derived from an alkane?

Write a balanced net ionic equation for the reaction of (a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\) with hydrochloric acid. (b) acetic acid with a solution of barium hydroxide. (c) 2-chloropropane with a solution of sodium hydroxide.

Draw structures for all the alcohols with molecular formula \(\mathrm{C}_{6} \mathrm{H}_{14} \mathrm{O}\).

Writean equation for the reaction of chloroaceticacid \(\left(K_{\mathrm{a}}=1.5 \times 10^{-3}\right)\) with trimethylamine \(\left(K_{\mathrm{b}}=5.9 \times 10^{-5}\right) .\) Calculate the equilibrium constant for the reaction. If \(0.10 M\) solutions of these two species are mixed, what will be their concentrations at equilibrium?