Chapter Questions
a. What is catenation?b. How does catenation contribute to the diversity of organic compounds?
a. What information about a compound is provided by a structural formula?b. How are structural formulas used in organic chemistry?
Can molecules with the molecular formulas $\mathrm{C}_{4} \mathrm{H}_{10}$ and $\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}$ be structural isomers of one another? Why or why not?
Can molecules with only single bonds (and no rings) have geometric isomers? Why or why not?
What are hydrocarbons, and what is their importance?
a. What do the terms saturated and unsaturated mean when applied to hydrocarbons?b. What other meanings do these terms have in chemistry?c. Classify alkenes, alkanes, alkynes, and aromatic hydrocarbons as either saturated or unsaturated.
Classify each of the following as an alkane, alkene, alkyne, or aromatic hydrocarbon.
Give the general formula for the members of the following:a. alkane seriesb. alkene seriesc. alkyne series
a. What is a homologous series?b. By what method are straight-chain hydrocarbons named?c. Name the straight-chain alkane with the molecular formula $\mathrm{C}_{10} \mathrm{H}_{22}$.
What are cycloalkanes?
a. What trend occurs in the boiling points of alkanes?b. How would you explain this trend?c. How is the trend in alkane boiling points used in petroleum fractional distillation?
Give examples of ethene’s commercial uses.
Give one use for ethyne.
What is the name of the parent hydrocarbon of simple aromatic hydrocarbons?
Name the following molecules. (Hint: See Sample Problem A.)
Give the complete, uncondensed, structural formula for each of the following alkanes. (Hint: See Sample Problem A.)a. decaneb. 3,3-dimethylpentane
Give the condensed structural formula for 2,2,4,4-tetramethylpentane.
For each of the following, determine whether the alkane is named correctly. If it is not, give the correct name.a. 1-methylpropaneb. nonanec. 4-methylhexaned. 4-ethyl-2-methylhexane
Name the following alkenes. (Hint: See Sample Problem B.)
Name the following alkynes:
Write the general formula for each of the following:a. alcoholb. etherc. alkyl halide
Based on the boiling points of water and methanol, in which would you expect to observe a greater degree of hydrogen bonding? Explain your answer.
a. Why is glycerol used in moisturizing skin lotions?b. How does this relate to the chemical structure of glycerol?
Write the general formula for each of the following:a. aldehyde $\quad$ b. ketone $\quad\quad$ c. carboxylic acidd. estere. amine
Aldehydes and ketones both contain the same functional group. Why are they classified as separate classes of organic compounds?
How are esters related to carboxylic acids?
What element do amines contain besides carbon and hydrogen?
Explain why an amine acts as a base.
What classes of organic compounds contain oxygen?
What type of chemical reaction would you expect to occur between 2-octene and hydrogen bromide, $\mathrm{HBr}$?
How many molecules of chlorine, $\mathrm{Cl}_{2},$ can be added to a molecule of 1 -propene? a molecule of 1 -propyne?
Compare substitution and addition reactions.
In a chemical reaction, two small molecules are joined, and a water molecule is produced. What type of reaction took place?
What are two reactions by which polymers can be formed?
What is the structural requirement for a molecule to be a monomer in an addition polymer?
Which of the following reactions is a substitution reaction?
Which of the following reactions is an addition reaction?
Which of the following reactions is a condensation reaction?
Which of the following reactions is an elimination reaction?
Classify each of the following reactions as an elimination reaction or a condensation reaction:
Classify each of the following reactions as a substitution reaction or an addition reaction:
Identify each of the following reactions as an addition, substitution, elimination, or condensation reaction:
Give the molecular formula for each type of hydrocarbon. Assume each contains seven carbon atoms.a. an alkaneb. an alkenec. an alkyne
a. Alkyne nomenclature is very similar to the nomenclature of what other group of hydrocarbons?b. How do these nomenclatures differ?
a. What are delocalized electrons?b. What is their effect on the reactivity of aromatic hydrocarbons?
Inferring Conclusions Why are organic compounds with covalent bonds usually less stable when heated than inorganic compounds with ionic bonds?
Inferring Relationships The element that appears in the greatest number of compounds is hydrogen. The element found in the second greatest number of compounds is carbon. Why are there more hydrogen compounds than carbon compounds?
Relating Ideas As the number of carbon atoms in an alkane molecule increases, does the percentage by mass of hydrogen increase, decrease, or remain the same?
Applying Ideas How does ethylene glycol protect radiator fluid in an automobile from both freezing in the winter and boiling over in the summer?
The top 10 chemicals produced in the United States are listed in Table 7B of the Elements Handbook (Appendix A). Review this material, and answer the following:a. Which of the top ten compounds are organic?b. Write structural formulas for the compounds you listed in item (a).c. To what homologous series do each of these compounds belong?
The reaction of methane with oxygen produces two different oxides of carbon. Review this material in the Elements Handbook (Appendix A), and answer the following:a. What condition determines whether the product of the methane reaction is $\mathrm{CO}_{2}$ or $\mathrm{CO}$?b. If a home heating system is fueled by natural gas, what difference does it make if the combustion produces $\mathrm{CO}_{2}$ or $\mathrm{CO}$?
Silicon is similar to carbon in forming long-chain compounds. Review the material on silicon in the Elements Handbook (Appendix A), and answer the following.a. How does a long-chain silicon compound differ in composition from a long-chain carbon compound?b. The simplest alkane is methane. Methyl groups are found in all alkanes. What is a common subunit of a silicate? What is the geometry of that subunit?
Mercury in the environment poses a hazard to living organisms. Review the section on mercury poisoning in the Elements Handbook (Appendix A).a. Draw a structural formula for the organic mercury compound described in that section.b. What is the IUPAC name for this compound?
Chemical and Engineering News publishes a list once a year of the top 50 chemicals. Find out which chemicals on the current year’s list are hydrocarbons, and report your findings to the class.
Consult reference materials at the library, and read about products made from hydrocarbons. Keep a list of the number of petroleum-related products you use in a single day.
The widespread use of synthetic polymers in modern society has led to a number of new environmental problems. Find out what some of these problems are and what can be done to reduce them.
Performance Models are often used to visualize the three-dimensional shape of molecules. Using gumdrops as atoms and toothpicks to bond them together, construct models of different hydrocarbons. Use large gumdrops for carbon and smaller gumdrops for hydrogen.
Performance Using your gumdrop models, demonstrate why alkenes can have geometric isomers, whilealkanes (except cycloalkanes) cannot.
Performance Devise a set of experiments to study how well biodegradable plastics break down. If your teacher approves your plan, conduct an experiment to test the procedure on products labeled “biodegradable.”
Performance Your teacher will make available unlabeled samples of benzoic acid, ethyl alcohol, and hexanediamine. Develop an experiment to identify each. If your teacher approves your plan, identify the unknown substances.
Keep a list of the food you consume in a single day. Compare the content labels from those foods, and then list the most commonly used chemicals in them. With the aid of your teacher and some reference books, try to classify the organic chemicals by their functional groups.
As a class or small group, research the preservatives used in various foods. Examine their chemical structures. Determine a way to test for organic functional groups of possibly hazardous preservatives.