Problem 4

. MAIN Idea Compare and contrast alkyl halides and aryl halides

Ibrahim A.

Numerade Educator

Problem 5

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}

Amy J.

Numerade Educator

Problem 6

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}

Ibrahim A.

Numerade Educator

Problem 7

Evaluate How would you expect the boiling points of propane and

1-chloropropane to compare? Explain your answer

Amy J.

Numerade Educator

Problem 8

Interpret Scientific Illustrations

Examine the pair of substituted

hydrocarbons illustrated at right, and

decide whether it represents a pair of

optical isomers. Explain your answer.

Ibrahim A.

Numerade Educator

Problem 9

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

Amy J.

Numerade Educator

Problem 10

Identify the functional group present in each of the following structures. Name

the substance represented by each structure.

Ibrahim A.

Numerade Educator

Problem 11

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}

Amy J.

Numerade Educator

Problem 12

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

Ibrahim A.

Numerade Educator

Problem 13

Analyze Based on the molecular structures below, which compound would you

expect to be more soluble in water? Explain your reasoning

Amy J.

Numerade Educator

Problem 14

4. MAIN Idea Classify each of the carbonyl compounds as one of the types of

organic substances you have studied in this section.

Ibrahim A.

Numerade Educator

Problem 15

Describe the products of a condensation reaction between a carboxylic acid

and an alcohol.

Amy J.

Numerade Educator

Problem 16

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.

Ibrahim A.

Numerade Educator

Problem 17

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.

Amy J.

Numerade Educator

Problem 18

MAIN Idea Classify each reaction as substitution, elimination, addition,

or condensation.

Ibrahim A.

Numerade Educator

Problem 19

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}

Amy J.

Numerade Educator

Problem 20

Complete each equation by writing the condensed structural formula for the

product that is most likely to form.

Ibrahim A.

Numerade Educator

Problem 21

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.

Amy J.

Numerade Educator

Problem 22

MAIN Idea 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

Ibrahim A.

Numerade Educator

Problem 23

Label the following polymerization reaction as addition or condensation. Explain

your answer.

Amy J.

Numerade Educator

Problem 24

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.

Ibrahim A.

Numerade Educator

Problem 25

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.

Amy J.

Numerade Educator

Problem 27

Describe and compare the structures of alkyl halides and

aryl halides.

Amy J.

Numerade Educator

Problem 28

What reactant would you use to convert methane to

bromomethane?

Ibrahim A.

Numerade Educator

Problem 29

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}

Amy J.

Numerade Educator

Problem 30

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.

Ibrahim A.

Numerade Educator

Problem 31

Circle and name each of the functional groups circled in

the structures shown in Figure 22.22.

Amy J.

Numerade Educator

Problem 32

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}

Ibrahim A.

Numerade Educator

Problem 33

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}

Amy J.

Numerade Educator

Problem 34

Draw and name all of the structural isomers possible

for an alkyl halide with no branches and the molecular

formula $C_{5} \mathrm{H}_{10} \mathrm{Br}_{2} .$

Ibrahim A.

Numerade Educator

Problem 35

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}

Amy J.

Numerade Educator

Problem 36

How is the compound shown in Figure 22.23

denatured? What is the name of the compound?

Ibrahim A.

Numerade Educator

Problem 37

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}

Amy J.

Numerade Educator

Problem 38

Explain why an alcohol molecule will always have a

higher solubility in water than an ether molecule having

an identical molecular mass.

Ibrahim A.

Numerade Educator

Problem 39

Explain why ethanol has a much higher boiling point

than aminoethane, even though their molecular masses

are nearly equal.

Amy J.

Numerade Educator

Problem 40

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}

Ibrahim A.

Numerade Educator

Problem 41

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}

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Problem 42

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}

Ibrahim A.

Numerade Educator

Problem 43

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}

Amy J.

Numerade Educator

Problem 44

What type of reaction is used to produce aspirin from

salicylic acid and acetic acid?

Ibrahim A.

Numerade Educator

Problem 45

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}

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Problem 47

Synthetic Organic Compounds What is the starting

material for making most synthetic organic compounds?

Amy J.

Numerade Educator

Problem 49

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}

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Problem 50

Classify each of the following organic reactions as substitution, addition, oxidation-reduction elimination, or

condensation

\begin{equation}

\begin{array}{l}{\text { a. } 2 \text { -butene }+\text { hydrogen } \rightarrow \text { butane }} \\ {\text { b. propane }+\text { fluorine } \rightarrow 2 \text { -fluoropropane }+\text { hydrogen }} \\ {\text { fluoride }} \\ {\text { c. } 2 \text { -propanol } \rightarrow \text { propene }+\text { water }} \\ {\text { d. cyclobutene + water } \rightarrow \text { cyclobutanol }}\end{array}

\end{equation}

Ibrahim A.

Numerade Educator

Problem 51

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}

Amy J.

Numerade Educator

Problem 52

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}

Ibrahim A.

Numerade Educator

Problem 53

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

Amy J.

Numerade Educator

Problem 54

Explain the difference between addition polymerization

and condensation polymerization.

Ibrahim A.

Numerade Educator

Problem 55

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

Amy J.

Numerade Educator

Problem 56

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}

Ibrahim A.

Numerade Educator

Problem 57

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}

Amy J.

Numerade Educator

Problem 58

Choose the polymer of each pair that you expect to have

the higher water solubility.

Ibrahim A.

Numerade Educator

Problem 59

Examine the structures of the following polymers in

Table 22.14. Decide whether each is made by addition

or condensation polymerization.

\begin{equation}

\begin{array}{ll}{\text { a. nylon }} & {\text { c. polyurethane }} \\ {\text { b. polyacrylonitrile }} & {\text { d. polypropylene }}\end{array}

\end{equation}

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Problem 60

Human Hormones Which halogen is found in

hormones made by a normal human thyroid gland?

Ibrahim A.

Numerade Educator

Problem 62

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}

Ibrahim A.

Numerade Educator

Problem 63

Name the type of organic compound formed by each of

the following reactions.

\begin{equation}

\begin{array}{l}{\text { a. elimination from an alcohol }} \\ {\text { b. addition of hydrogen chloride to an alkene }} \\ {\text { c. addition of water to an alkene }} \\ {\text { d. substitution of a hydroxyl group for a halogen atom }}\end{array}

\end{equation}

Amy J.

Numerade Educator

Problem 64

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}

Ibrahim A.

Numerade Educator

Problem 65

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}

Amy J.

Numerade Educator

Problem 66

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}

Ibrahim A.

Numerade Educator

Problem 67

Interpret Scientific Illustrations List all the functional

groups present in each of the following complex organic

molecules

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Problem 68

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.

Ibrahim A.

Numerade Educator

Problem 69

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}

Amy J.

Numerade Educator

Problem 70

Interpret Scientific Illustrations Human cells

require vitamin $C$ to properly synthesize materials

that make up connective tissue such as that found in

ligaments. List the functional groups present in the

Vitamin $\mathrm{C}$ molecule shown in Fiqure 22.24

Ibrahim A.

Numerade Educator

Problem 71

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}

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Problem 72

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.

Ibrahim A.

Numerade Educator

Problem 73

Evaluate Examine Table 22.15 comparing some

alcohols and their solubility in water. Use the table to

answer the following questions.

\begin{equation}

\begin{array}{l}{\text { a. What type of bond forms between the -OH group of }} \\ {\text { alcohols and water? }} \\ {\text { b. State a relationship between water solubility and }} \\ {\text { alcohol size from the data in the table. }} \\ {\text { c. Provide an explanation for the relationship you stated }} \\ {\text { in Part b. }}\end{array}

\end{equation}

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Problem 74

Recognize Most useful organic molecules are made

from raw materials using several steps. This is called a

multistep synthesis pathway. Label the types of reaction

or process taking place in each step of the multistep synthesis pathway below.

\begin{equation}

\begin{array}{l}{\text { petroleum } \rightarrow \text { ethane } \rightarrow \text { chloroethane } \rightarrow \text { ethene } \rightarrow} \\ {\text { ethanol } \rightarrow \text { ethanoic (acetic) acid }}\end{array}

\end{equation}

Ibrahim A.

Numerade Educator

Problem 75

Animal Pheromones Catnip contains an organic

chemical known as nepetalactone, shown in Figure $22.25,$

that is thought to mimic feline sex pheromones. Cats

will rub in it, roll over it, paw at it, chew it, lick it, leap

about, then purr loudly, growl, and meow for several

minutes before losing interest. It takes up to two hours

for the cat to "reset" and then have the same response to

the catnip.

\begin{equation}

\begin{array}{l}{\text { a. What type of organic compound is nepetalactone? }} \\ {\text { b. Draw the structural formula for nepetalactone on }} \\ {\text { a sheet of paper and then draw in all the missing }} \\ {\text { hydrogen atoms. Remember that carbon atoms must }} \\ {\text { have four bonds to be stable. }} \\ {\text { c. Write the molecular formula for nepetalactone. }}\end{array}

\end{equation}

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Problem 76

Explain why the concentration of ozone over Antarctica

decreases at about the same time every year. (Chapter 1)

Ibrahim A.

Numerade Educator

Problem 77

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}

Amy J.

Numerade Educator

Problem 78

Determine the number of atoms in each of the following.

(Chapter 10)

\begin{equation}

\text { a. }56.1 \mathrm{g} \text { Al } \quad \text { b. } 2 \text { moles } \mathrm{C}

\end{equation}

Ibrahim A.

Numerade Educator

Problem 80

According to Le Chatelier's principle, how would

increasing the volume of the reaction vessel affect the

equilibrium $2 \mathrm{SO}_{2}(\mathrm{g})+\mathrm{O}_{2}(\mathrm{g}) \rightarrow 2 \mathrm{SO}_{3}(\mathrm{g}) ?$ (Chapter 17$)$

Ibrahim A.

Numerade Educator

Problem 81

Compare and contrast saturated and unsaturated hydrocarbons. (Chapter 21)

Amy J.

Numerade Educator

Problem 82

Historical Perspective Write a short story describing

how your life would differ if you lived in the 1800s,

before the development of synthetic polymers.

Ibrahim A.

Numerade Educator

Problem 83

After one dose of the drug beclomethasone was given,

which propellant resulted in the highest concentration of medication in the blood, HFA or CFC?

Amy J.

Numerade Educator

Problem 85

Only one-half the amount of medication is needed

with the HFA propellant when compared to the CFC

propellant to achieve a similar blood-concentration

level. Infer the advantages of using a lower dose of

medication to get similar results.

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