Chapter 23

Give the molecular formula of an alkane with 30 carbon atoms.

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

Draw structural formulas of an alkane, a cycloalkane, an alkene, and an aromatic hydrocarbon, each with seven carbon atoms.

Explain why there are two isomers of 2 -butene. Draw their structural formulas and name the isomers.

Draw structural formulas for the isomers of ethylmethylbenzene.

Give condensed structural formulas of all possible substitution products of ethane and \(\mathrm{Cl}_{2}\).

Define the terms substitution reaction and addition reaction. Give examples of each.

What would you expect to be the major product when two molecules of HCl add successively to acetylene? Explain.

Write the structure of propylbenzene. Write the structure of \(p\) -dichlorobenzene.

What is a functional group? Give an example and explain how it fits this definition.

An aldehyde contains the carbonyl group. Ketones, carboxylic acids, and esters also contain the carbonyl group. What distinguishes these latter compounds from an aldehyde?

Identify and name the functional group in each of the following. a. \(\mathrm{CH}_{3} \mathrm{COCH}_{3}\) b. \(\mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{CH}_{3}\) c. \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CH}_{2}\) d. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH}\) e. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CHO}\) f. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\)

Which of the following could exist as a cis-trans isomer? a. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) b. CCC(C)C c. CC(C)C d. \(\mathrm{CH}_{3} \mathrm{CHCHCH}_{3}\) e. none of these

The correct formula for butane is a. \(\mathrm{C}_{2} \mathrm{H}_{6}\) b. \(\mathrm{C}_{8} \mathrm{H}_{18}\) c. \(\mathrm{CH}_{4}\) d. \(\mathrm{C}_{4} \mathrm{H}_{10}\) e. \(\mathrm{C}_{3} \mathrm{H}_{6}\)

What is the correct IUPAC name for the following compound? CCC(C)CO a. 2 -ethyl-3-hexanol b. 3 -ethyl-2-butanol c. 3 -methyl-2-pentanol d. 3-methyl-4-pentanol e. 2 -ethyl-3-butanol

Explain why you wouldn't expect to find a compound with the formula \(\mathrm{CH}_{5}\).

Why would you expect the melting points of the alkanes to increase in the series methane, ethane, propane, and so on?

Consider the following formulas of two esters: CCC(=O)OC CCOC(C)=O One of these is ethyl ethanoate (ethyl acetate) and one is methyl propanoate (methyl propionate). Which is which?

Write an equation for a possible substitution reaction of ethane, \(\mathrm{C}_{2} \mathrm{H}_{6}\), with \(\mathrm{Cl}_{2}\)

Write an equation for a possible substitution reaction of propane, \(\mathrm{C}_{3} \mathrm{H}_{8}\), with \(\mathrm{Br}_{2}\).

What is the major product when \(\mathrm{HBr}\) is added to methylpropene?

Write the condensed structural formula for each of the following compounds. a. 2,3 -dimethylhexane b. 3 -ethylhexane c. 2-methyl-4-isopropylheptane d. \(2,2,3,3\) -tetramethylpentane

Write the condensed structural formula for each of the following compounds. a. 2,2 -dimethylpentane b. 3 -ethyl-2-methylhexane c. 3 -ethyl-4-methyloctane d. \(3,4,4,5\) -tetramethylheptane

Give the condensed structural formula for each of the following compounds. a. 3 -ethyl-2-pentene b. 4 -ethyl-2-methyl-2-hexene

Write the condensed structural formula for each of the following compounds. a. 2,3 -dimethyl-2-pentene b. 2 -methyl-4-propyl-3-heptene

Give the IUPAC names and include the cis or trans label for each of the isomers of \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}_{2} \mathrm{CH}_{3}\)

Give the IUPAC names and include the cis or trans label for each of the isomers of \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}_{3}\).

Write structural formulas for (a) \(1,1,1\) -triphenylethane; (b) \(o\) -ethylmethylbenzene.

Write structural formulas for (a) \(1,2,3\) -trimethylbenzene; (b) \(p\) -diethylbenzene.

Write the structural formula for each of the following compounds. a. isopropyl propionate b. \(t\) -butylamine c. 2,2 -dimethylhexanoic acid d. \(c i s-3\) -hexene

Write the structural formula for each of the following compounds. a. 3 -ethyl-1-pentene b. \(1,1,2,2\) -tetraphenylethane c. 1 -phenyl-2-butanone d. cyclopentanone

Describe chemical tests that could distinguish between: a. propionaldehyde (propanal) and acetone (propanone) b. \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{C} \equiv \mathrm{C}-\mathrm{CH}=\mathrm{CH}_{2}\) and benzene

Describe chemical tests that could distinguish between: a. acetic acid and acetaldehyde (ethanal) b. toluene (methylbenzene) and 2-methylcyclohexene

Identify each of the following compounds. a. A gas with a sweetish odor that promotes the ripening of green fruit. b. An unsaturated compound of the formula \(\mathrm{C}_{7} \mathrm{H}_{8}\) that gives a negative test with bromine in carbon tetrachloride. c. A compound with an ammonia-like odor that acts as a base; its molecular formula is \(\mathrm{CH}_{5} \mathrm{~N}\). d. An alcohol used as a starting material for the manufacture of formaldehyde.

Identify each of the following compounds. a. An acidic compound that also has properties of an aldehyde; its molecular formula is \(\mathrm{CH}_{2} \mathrm{O}_{2}\). b. A compound used as a preservative for biological specimens and as a raw material for plastics. c. A saturated hydrocarbon boiling at \(0^{\circ} \mathrm{C}\) that is liquefied and sold in cylinders as a fuel. d. A saturated hydrocarbon that is the main constituent of natural gas.

Draw the condensed structural formulas for a primary, a secondary, and a tertiary alcohol, each containing five carbon atoms.

Write the condensed structural formulas of a ketone and an ester, each containing four carbon atoms.

You encounter a hydrocarbon with the name 2 -ethyl-3methylhexane. Is this a proper IUPAC name? If not, what is the proper IUPAC name? To answer this question, start by writing the condensed structural formula based on this name.

Consider the molecule \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CHCH}_{3}\). a. Write a structural formula of the cis isomer. b. Name the molecule from part a. c. Write the condensed structural formula of the major product of the reaction of the molecule with \(\mathrm{Br}_{2}\).

Write the condensed structural formula for each of the following. a. An aldehyde that contains four carbon atoms. b. An ether that contains six carbon atoms. c. An aromatic hydrocarbon with methyl groups at positions 1 and \(5 .\) d. A secondary amine that contains five carbon atoms. e. An alkyne that contains four carbon atoms.