Chapter 22

Name the alkyl or aryl halide whose structure is shown.

Name the alkyl or aryl halide whose structure is shown.

Compare and contrast alkyl halides and aryl halides.

Define functional group and name the group present in each of the following structures. Name the type of organic compound each substance represents. $$ \begin{array}{l}{\text { a. } \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}} \\ {\text { b. } \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{F}} \\\ {\text { c. } \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}}\end{array} $$ $$ \begin{array}{c}{\text { d. } 0} \\ {\mathrm{CH}_{3} \mathrm{C}-\mathrm{OH}}\end{array} $$

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

Identify two elements that are commonly found in functional groups.

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

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

Classify each of the carbonyl compounds as one of the types of organic substances you have studied in this section.

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

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

Infer why water-soluble organic compounds with carboxyl groups exhibit achibit 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. \(\begin{array}{ll}{\text { a. alkyl halide } \rightarrow \text { alkene }} & {\text { c.alcohol }+\text { carboxylic acid } \rightarrow \text { ester }} \\\ {\text { b. alkene } \rightarrow \text { alcohol }} & {\text { d. alkene } \rightarrow \text { alkyl dihalide }}\end{array}\)

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.

Draw the structure for the polymer that could be produced from each of the following monomers by the method stated. a. Addition \(\quad\) b. Condensation

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

Predict the physical properties of the polymer that is made from the following monomer. Mention solubility in water, electrical conductivity, texture, and chemical reactivity. Do you think it will be thermoplastic or thermosetting? Give reasons for your predictions.

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 condensed formulas. $$ \begin{array}{l}{\text { a. } C H_{3}\left(C H_{2}\right)_{3} C H_{2} N H_{2}} \\\ {\text { b. } C H_{3}\left(C H_{2}\right)_{5} C H_{2} N H_{2}} \\ {\text { c. } C H_{3}\left(C H_{2}\right)_{2} C H\left(N H_{2}\right) C H_{3}} \\\ {\text { d. } C H_{3}\left(C H_{2}\right)_{8} C H_{2} N H_{2}}\end{array} $$

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. $$ \begin{array}{l}{\text { a. chlorobenzene }} \\ {\text { b. } 1 \text { -bromo-4-chlorohexane }} \\ {\text { c. } 1,2 \text { -difluoro-3-iodocyclohexane }} \\ {\text { d. } 1,3 \text { -dibromobenzene }} \\ {\text { e. } 1,1,2,2 \text { -tetrafluoroethane }}\end{array} $$

For 1 -bromo-2-chloropropane: a. Draw the structure. b. Does the compound have optical isomers? c. If the compound has optical isomers, identify the chiral carbon atom.

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

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

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

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. \(\begin{array}{lll}{\text { a. } 1 \text { -butanol }} & {\text { b. } 2 \text { -hexanol }}\end{array}\)

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

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

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

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

Draw structures for each of the following carbonyl compounds. a. \(2,2\) -dichloro- 3 -pentanone b. 4 -methylpentanal c. isopropyl hexanoate d. octanoamide e. 3 -fluoro-2-methylbutanoic acid f. cyclopentanal g. hexyl methanoate

Synthetic Organic Compounds What is the starting material for making most synthetic organic compounds?

Explain the importance of classifying reactions.

List the type of organic reaction needed to perform each of the following transformations. a. alkene \(\rightarrow\) alkane b. alkyl halide \(\rightarrow\) alcohol c. alkyl halide \(\rightarrow\) alkene d. amine \(+\) carboxylic acid \(\rightarrow\) amide e. alcohol \(\rightarrow\) alkyl halide f. alkene \(\rightarrow\) alcohol

Classify each of the following organic reactions as substitution, addition, oxidation-reduction elimination, or condensation. a. 2 -butene \(+\) hydrogen \(\rightarrow\) butane b. propane \(+\) fluorine \(\rightarrow 2\) -fluoropropane \(+\) hydrogen fluoride c. 2 -propanol \(\rightarrow\) propene \(+\) water d. cyclobutene \(+\) water \(\rightarrow\) cyclobutanol

Use structural formulas to write equations for the fol- lowing reactions. a. the substitution reaction between 2 -chloropropane and water yielding 2 -propanol and hydrogen chloride b. the addition reaction between 3 -hexene and chlorine yielding \(3,4\) -dichlorohexane

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

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? a. polyethylene b. polyethylene terephthalate c. polytetrafluoroethylene

Name the polymers made from the following monomers. $$ \text { a. }C F_{2}=C F_{2} \quad \text { b. } C H_{2}=C C l_{2} $$

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

Describe the properties of carboxylic acids.

Draw structures of the following compounds. \(\begin{array}{ll}{\text { a. butanone }} & {\text { c. hexanoic acid }} \\\ {\text { b. propanal }} & {\text { d. heptanoamide }}\end{array}\)

Name the type of organic compound formed by each of the following reactions. a. elimination from an alcohol b. addition of hydrogen chloride to an alkene c. addition of water to an alkene d. substitution of a hydroxyl group for a halogen atom

List two uses for each of the following polymers. \(\begin{array}{ll}{\text { a. polypropylene }} & {\text { c. polytetrafluororoethylene }} \\ {\mathbf{b} . \text { polyurethane }} & {\text { d. polyvinvyl chloride }}\end{array}\)