Chapter 22

What kinds of molecules often trigger our sense of smell?

Why does silicon exhibit less diversity of compounds than carbon does?

Describe the geometry and hybridization about a carbon atom that forms a. four single bonds. b. two single bonds and one double bond. c. one single bond and one triple bond.

What are hydrocarbons? What are their main uses?

What are the main classifications of hydrocarbons? What are their generic molecular formulas?

Explain the differences between a structural formula, a condensed structural formula, a carbon skeleton formula, a ball-and-stick model, and a space-filling model.

What are structural isomers? How do the properties of structural isomers differ from one another?

What are optical isomers? How do the properties of optical isomers differ from one another?

Define each term related to optical isomerism: enantiomers, chiral, dextrorotatory, levorotatory, racemic mixture.

What is the difference between saturated and unsaturated hydrocarbons?

What are the key differences in the way that alkanes, alkenes, and alkynes are named?

What are the key differences in the way that alkanes, alkenes, and alkynes are named?

Describe and provide an example of a hydrocarbon combustion reaction.

What kinds of reactions are common to alkanes? List an example of each.

Describe each kind of reaction. a. substitution reaction b. addition reaction c. elimination reaction

What kinds of reactions are common to alkenes? Give an example of each.

Explain Markovnikov's rule and give an example of a reaction to which it applies.

What is the structure of benzene? What are the different ways in which this structure is represented?

What is a functional group? List some examples.

What is the generic structure of alcohols? Write the structures of two specific alcohols.

Explain oxidation and reduction with respect to organic compounds.

What kinds of reactions are common to alcohols? Provide an example of each.

What are the generic structures for aldehydes and ketones? Write a structure for a specific aldehyde and ketone.

What are the generic structures for carboxylic acids and esters? Write a structure for a specific carboxylic acid and ester.

What kinds of reactions are common to carboxylic acids and esters? Provide an example of each.

What is the generic structure of amines? Write the structures of two specific amines.

Based on the molecular formula, determine whether each compound is an alkane, alkene, or alkyne. (Assume that the hydrocarbons are noncyclical and there is no more than one multiple bond.) a. \(\mathrm{C}_{5} \mathrm{H}_{12}\) b. \(\mathrm{C}_{3} \mathrm{H}_{6}\) c.\(\mathrm{C}_{7} \mathrm{H}_{12}\) d. \(\mathrm{C}_{11} \mathrm{H}_{22}\)

Based on the molecular formula, determine whether each compound is an alkane, alkene, or alkyne. (Assume that the hydrocarbons are noncyclical and there is no more than one multiple bond.) a. \(\mathrm{C}_{8} \mathrm{H}_{16}\) b. \(\mathrm{C}_{4} \mathrm{H}_{6}\) c. \(C_{7} H_{16}\) d. \(\mathrm{C}_{2} \mathrm{H}_{2}\)

Write structural formulas for each of the nine structural isomers of heptane.

Write structural formulas for any 6 of the 18 structural isomers of octane.

Draw a structure for each alkane. a. 3 -ethylhexane b. 3 -ethyl-3-methylpentane c. 2,3 -dimethylbutane d. 4,7 -diethyl- 2,2 -dimethylnonane

Draw a structure for each alkane. a. 2,2 -dimethylpentane b. 3 -isopropylheptane c. 4 -ethyl-2,2-dimethylhexane d. 4,4 -diethyloctane

Complete and balance each hydrocarbon combustion reaction. a. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{3}+\mathrm{O}_{2} \longrightarrow\) b. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH} \equiv \mathrm{CH}_{2}+\mathrm{O}_{2} \longrightarrow\) \(\mathbf{c .} \mathbf{C H} \equiv \mathrm{CH}+\mathrm{O}_{2} \longrightarrow\)

Complete and balance each hydrocarbon combustion reaction. a. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}+\mathrm{O}_{2} \longrightarrow\) b. \(\mathrm{CH}_{2}=\mathrm{CHCH}_{3}+\mathrm{O}_{2} \longrightarrow\) c. \(\mathrm{CH} \equiv \mathrm{CCH}_{2} \mathrm{CH}_{3}+\mathrm{O}_{2} \longrightarrow\)

List all the possible products for each alkane substitution reaction. (Assume monosubstitution.) a. \(\mathrm{CH}_{4}+\mathrm{Cl}_{2} \longrightarrow\) b. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Br}+\mathrm{Br}_{2} \longrightarrow\) c. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}+\mathrm{Cl}_{2} \longrightarrow\) d. \(\mathrm{CH}_{3} \mathrm{CHBr}_{2}+\mathrm{Br}_{2} \longrightarrow\)

Write structural formulas for each of the possible isomers of n-hexene that are formed by moving the position of the double bond.

Write structural formulas for each of the possible isomers of \(n\) -pentyne that are formed by moving the position of the triple bond.

Draw the correct structure for each compound. a. 4 -octyne b. 3 -nonene c. 3,3 -dimethyl-1-pentyne d. 5 -ethyl-3,6-dimethyl-2-heptene

Draw the correct structure for each compound. a. 2 -hexene b. 1 -heptyne c. 4,4 -dimethyl- 2 -hexene d. 3 -ethyl-4-methyl-2-pentene

Draw the structure for each compound. a. isopropylbenzene b. meta-dibromobenzene c. 1 -chloro-4-methylbenzene

Draw the structure for each compound. a. ethylbenzene b. 1 -iodo-2-methylbenzene c. para-diethylbenzene

Draw the structure for each alcohol. a. 2 -butanol b. 2 -methyl- 1 -propanol c. 3 -ethyl-1-hexanol d. 2 -methyl-3-pentanol

Draw the structure of each aldehyde or ketone. a. hexanal b. 2 -pentanone c. 2 -methylbutanal d. 4 -heptanone

Draw the structure of each carboxylic acid or ester. a. pentanoic acid b. methyl hexanoate c. 3 -ethylheptanoic acid d. butyl ethanoate

Name each ether a. \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{2}-\mathrm{CH}_{3}\) b. \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{2}-\mathrm{CH}_{3}\) c. \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{3}\) d. \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{3}\)

Draw the structure for each ether. a. ethyl propyl ether b. dibutyl ether c. methyl hexyl ether d. dipentyl ether

Draw the structure for each amine. a. isopropylamine b. triethylamine c. butylethylamine

Classify each amine reaction as acid–base or condensation and list its products. a. \(\mathrm{CH}_{3} \mathrm{NHCH}_{3}+\mathrm{HCl} \longrightarrow\) b. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH} \longrightarrow\) c. \(\mathrm{CH}_{3} \mathrm{NH}_{2}+\mathrm{H}_{2} \mathrm{SO}_{4} \longrightarrow\)

Draw the structure that corresponds to each name and indicate which structures can exist as stereoisomers. a. 3 -methyl-1-pentene b. 3,5 -dimethyl- 2 -hexene c. 3 -propyl-2-hexene

There are 11 structures (ignoring stereoisomerism) with the formula \(\mathrm{C}_{4} \mathrm{H}_{8} \mathrm{O}\) that have no carbon branches. Draw the structures and identify the functional groups in each.