Chapter 22

Draw structures for the following molecules \begin{equation} \begin{array}{ll}{\text { a. } 2 \text { -chlorobutane }} & {\text { c. } 1,1,1 \text { -trichloroethane }} \\ {\text { b. } 1,3 \text { -diflurohexane }} & {\text { d. } 4 \text { -bromo-1-chlorobenzene }}\end{array} \end{equation}

Define functional group and name the group present in each of the following structures. Name the type of organic compound each substance represents. \begin{equation} \begin{array}{l}{\text { a. } \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}} \\ {\mathrm{b} . \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{F}} \\\ {\mathrm{c} \cdot \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}}\end{array} \end{equation}

Evaluate How would you expect the boiling points of propane and 1-chloropropane to compare? Explain your answer

MAIN Idea Identify two elements that are commonly found in functional groups.

Draw the structure for each molecule \begin{equation} \begin{array}{ll}{\text { a. } 1 \text { -propanol }} & {\text { c.propyl ether }} \\ {\text { b. } 1,3 \text { -cyclopentanediol }} & {\text { d. } 1,2 \text { -propanediamine }}\end{array} \end{equation}

Discuss the properties of alcohols, ethers, and amines, and give one use of each.

Describe the products of a condensation reaction between a carboxylic acid and an alcohol.

Determine The general formula for alkanes is \(C_{n} H_{2 n+2}\) . Derive a general formula to represent an aldehyde, a ketone, and a carboxylic acid.

Infer why water-soluble organic compounds with carboxyl groups exhibit acidic properties in solutions, whereas similar compounds with aldehyde structures do not exhibit these properties.

Identify the type of organic reaction that would best accomplish each conversion. \begin{equation} \begin{array}{ll}{\text { a. alkyl halide } \rightarrow \text { alkene }} & {\text { c. alcohol }+\text { carboxylic acid } \rightarrow \text { ester }} \\\ {\text { b. alkene } \rightarrow \text { alcohol }} & {\text { d. alkene } \rightarrow \text { alkyl dihalide }}\end{array} \end{equation}

Predicting Products Explain why the hydration reaction involving 1-butene might yield two distinct products, whereas the hydration of 2-butene yields only one product.

Identify Synthetic polymers often replace stone, wood, metals, wool, and cotton in many applications. Identify some advantages and disadvantages of using synthetic materials instead of natural materials.

What is a functional group?

Describe and compare the structures of alkyl halides and aryl halides.

What reactant would you use to convert methane to bromomethane?

Name the amines represented by each of the \begin{equation} \begin{array}{l}{\text { a. } \mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}} \\ {\text { b. } \mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{5} \mathrm{CH}_{2} \mathrm{NH}_{2}} \\ {\text { c. } \mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}} \\ {\text { d. } \mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{\mathrm{g}} \mathrm{CH}_{2} \mathrm{NH}_{2}}\end{array} \end{equation}

Explain why the boiling points of alkyl halides increase in order going down the column of halides in the periodic table, from fluorine through iodine.

Draw structures for these alkyl and aryl halides. \begin{equation} \begin{array}{l}{\text { a. chlorobenzene }} \\ {\text { b. } 1 \text { -bromo-4-chlorohexane }} \\ {\text { c. } 1,2 \text { -difluoro-3-iodocyclohexane }} \\ {\text { d. } 1,3 \text { -dibromobenzene }} \\ {\text { e. } 1,1,2,2 \text { - tetrafluoroethane }}\end{array} \end{equation}

For 1-bromo-2-chloropropane: \begin{equation} \begin{array}{l}{\text { a. Draw the structure. }} \\ {\text { b. Does the compound have optical isomers? }} \\ {\text { c. If the compound has optical isomers, identify the }} \\ {\text { chiral carbon atom. }}\end{array} \end{equation}

Draw and name all of the structural isomers possible for an alkyl halide with no branches and the molecular formula \(C_{5} \mathrm{H}_{10} \mathrm{Br}_{2} .\)

Name one structural isomer created by changing the position of one or more halogen atoms in each alkyl halide. \begin{equation} \begin{array}{ll}{\text { a. } 2 \text { -chloropentane }} & {\text { c. } 1,3 \text { -dibromocyclopentane }} \\ {\text { b. } 1,1 \text { -difluropropane }} & {\text { d. } 1 \text { -bromo- } 2 \text { -chloroethane }}\end{array} \end{equation}

Practical Applications Name one alcohol, amine, or ether that is used for each of the following purposes. \begin{equation} \begin{array}{ll}{\text { a. antiseptic }} & {\text { c. antifreeze }} \\\ {\text { b. solvent in paint }} & {\text { d. anesthetic }} \\ {\text { strippers }} & {\text { e. dye production }}\end{array} \end{equation}

Explain why an alcohol molecule will always have a higher solubility in water than an ether molecule having an identical molecular mass.

Explain why ethanol has a much higher boiling point than aminoethane, even though their molecular masses are nearly equal.

Name one ether that is a structural isomer of each alcohol. \begin{equation} \text{ a. }1 \text { -butanol } \quad \text { b. } 2 \text { -hexanol} \end{equation}

Draw structures for the following alcohol, amine, and ether molecules \begin{equation} \begin{array}{ll}{\text { a. } 1,2 \text { -butanediol }} & {\text { e. butyl pentyl ether }} \\ {\text { b. } 5 \text { -aminohexane }} & {\text { f. cyclobutyl methyl ether }} \\ {\text { c. isopropyl ether }} & {\text { g. } 1,3-\text { diaminobutane }} \\ {\text { d. } 2 \text { -methyl-1-butanol }} & {\text { h. cyclopentanol }}\end{array} \end{equation}

Draw the general structure for each of the following classes of organic compounds. \begin{equation} \begin{array}{ll}{\text { a. aldehyde }} & {\text { d. ester }} \\ {\text { b. ketone }} & {\text { e. amide }} \\ {\text { c. carboxylic acid }}\end{array} \end{equation}

Common Uses Name an aldehyde, ketone, carboxylic acid, ester, or amide used for each of the following purposes. \begin{equation} \begin{array}{l}{\text { a. preserving biological specimens }} \\ {\text { b. solvent in fingernail polish }} \\ {\text { c. acid in vinegar }} \\ {\text { d. flavoring in foods and beverages }}\end{array} \end{equation}

What type of reaction is used to produce aspirin from salicylic acid and acetic acid?

Draw structures for each of the following carbonyl compounds. \begin{equation} \begin{array}{l}{\text { a. } 2,2 \text { -dichloro-3 -pentanone }} \\ {\text { b. } 4 \text { -methylpentanal }} \\ {\text { c. isopropyl hexanoate }} \\\ {\text { d. octanoamide }} \\ {\text { e. } 3 \text { -fluoro- } 2 \text { -methylbutanoic acid }} \\ {\text { g. cyclopentanal }} \\ {\text { f. hexyl methanoate }}\end{array} \end{equation}

Explain the importance of classifying reactions.

List the type of organic reaction needed to perform each of the following transformations. \begin{equation} \begin{array}{l}{\text { a. alkene } \rightarrow \text { alkane }} \\ {\text { b. alkyl halide } \rightarrow \text { alcohol }} \\ {\text { c. alkyl halide } \rightarrow \text { alkene }} \\ {\text { d. amine + carboxylic acid } \rightarrow \text { amide }} \\ {\text { e. alcohol } \rightarrow \text { alkyl halide }} \\ {\text { f. alkene } \rightarrow \text { alcohol }}\end{array} \end{equation}

Use structural formulas to write equations for the following reactions. \begin{equation} \begin{array}{l}{\text { a. the substitution reaction between } 2 \text { -chloropropane }} \\ {\text { and water yielding } 2 \text { -propanol and hydrogen chloride }} \\ {\text { b. the addition reaction between } 3 \text { -hexene and chlorine }} \\ {\text { yielding } 3,4-\text { dichlorohexane }}\end{array} \end{equation}

What type of reaction converts an alcohol into each of the following types of compounds? \begin{equation} \begin{array}{ll}{\text { a. ester }} & {\text { c. alkene }} \\ {\text { b. alkyl halide }} & {\text { d. aldehyde }}\end{array} \end{equation}

Use structural formulas to write the equation for the condensation reaction between ethanol and propanoic acid.

Explain the difference between addition polymerization and condensation polymerization.

Which type of polymer is easier to recycle, thermosetting or thermoplastic? Explain your answer.

Manufacturing Polymers What monomers react to make each polymer? \begin{equation} \begin{array}{l}{\text { a. polyethylene }} \\ {\text { b. polyethylene terephthalate }} \\ {\text { c. polytetrafluoroethylene }}\end{array} \end{equation}

Name the polymers made from the following monomers. \begin{equation} \text { a. }\mathrm{CF}_{2}=\mathrm{CF}_{2} \quad \text { b. } \mathrm{CH}_{2}=\mathrm{CCl}_{2} \end{equation}

Human Hormones Which halogen is found in hormones made by a normal human thyroid gland?

Describe the properties of carboxylic acids.

Describe the properties of carboxylic acids. Draw structures of the following compounds. \begin{equation} \begin{array}{ll}{\text { a. butanone }} & {\text { c. hexanoic acid }} \\\ {\text { b. propanal }} & {\text { d. heptanoamide }}\end{array} \end{equation}

List two uses for each of the following polymers. \begin{equation} \begin{array}{ll}{\text { a. polypropylene }} & {\text { c. polytetrafluoroethylene }} \\ {\text { b. polyurethane }} & {\text { d. polyvinvl chloride }}\end{array} \end{equation}

Draw structures of and supply names for the organic compounds produced by reacting ethene with each of the following substances. \begin{equation} \begin{array}{ll}{\text { a. water }} & {\text { c. hydrogen chloride }} \\\ {\text { b. hydrogen }} & {\text { d. fluorine }}\end{array} \end{equation}

Environmentally-Safe Propellants Hydrofluoroalkanes (HFAs) are replacing chlorofluorocarbons in hand-held asthma inhalers, because of \(\mathrm{CFC}\) damage to the ozone layer. Draw the structures of the HFAs listed below. \begin{equation} \begin{array}{l}{\text { a. } 1,1,1,2,3,3,3 \text { -heptafluoropropane }} \\\ {\text { b. } 1,1,1,2, \text { - tetrafluoroethane }}\end{array} \end{equation}

Evaluate Ethanoic acid (acetic acid) is very soluble in water. However, naturally occurring long- chain carboxylic acids, such as palmitic acid \(\left(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{14} \mathrm{COOH}\right),\) are insoluble in water. Explain.

Communicate Write structural formulas for all structural isomers of molecules having the following formulas. Name each isomer. \begin{equation} \mathbf{a} \cdot \mathrm{C}_{3} \mathrm{H}_{8} \mathrm{O} \quad \text { b. } \mathrm{C}_{2} \mathrm{H}_{4} \mathrm{Cl}_{2} \end{equation}

Identify Draw the structure of an example of an organic molecule that has four carbons and falls into each of the compound types listed. \begin{equation} \begin{array}{ll}{\text { a. ester }} & {\text { c. ether }} \\ {\text { b. aldehyde }} & {\text { d. alcohol }}\end{array} \end{equation}

Predict A monohalogenation reaction describes a substitution reaction in which a single hydrogen atom is replaced by a halogen. A dihalogenation reaction is a reaction in which two hydrogen atoms are replaced by \begin{equation} \begin{array}{l}{\text { a. Draw the structures of all the possible monohaloge- }} \\ {\text { nation products that can form when pentane reacts }} \\ {\text { with } \mathrm{Cl}_{2} \text { . }} \\ {\text { b. Draw the structures of all the possible dihalogenation }} \\ {\text { products that can form when pentane reacts with } \mathrm{Cl}_{2} \text { . }}\end{array} \end{equation} two halogen atoms.

Why do the following characteristics apply to transition metals? (Chapter 6\()\) \begin{equation} \begin{array}{l}{\text { a. Ions vary in charge. }} \\ {\text { b. Many of their solids are colored. }} \\ {\text { c. Many are hard solids. }}\end{array} \end{equation}