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Glencoe Chemistry: Matter and Change

Buthelezi ,Dingrando,Wistrom,Zike

Chapter 22

Substituted Hydrocarbons and Their Reactions

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Problem 1

CAN'T COPY THE PROBLEM

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Problem 2

CAN'T COPY THE PROBLEM

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Problem 3

CAN'T COPY THE PROBLEM

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Problem 4

. MAIN Idea Compare and contrast alkyl halides and aryl halides

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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}

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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}

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Problem 7

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

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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.

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Problem 9

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

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Problem 10

Identify the functional group present in each of the following structures. Name
the substance represented by each structure.

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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}

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Problem 12

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

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Problem 13

Analyze Based on the molecular structures below, which compound would you
expect to be more soluble in water? Explain your reasoning

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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.

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Problem 15

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

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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.

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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.

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Problem 18

MAIN Idea Classify each reaction as substitution, elimination, addition,
or condensation.

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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}

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Problem 20

Complete each equation by writing the condensed structural formula for the
product that is most likely to form.

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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.

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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

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Problem 23

Label the following polymerization reaction as addition or condensation. Explain
your answer.

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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.

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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.

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Problem 26

What is a functional group?

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Problem 27

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

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Problem 28

What reactant would you use to convert methane to
bromomethane?

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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}

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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.

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Problem 31

Circle and name each of the functional groups circled in
the structures shown in Figure 22.22.

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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}

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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}

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Problem 34

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

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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}

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Problem 36

How is the compound shown in Figure 22.23
denatured? What is the name of the compound?

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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}

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Problem 38

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

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Problem 39

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

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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}

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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}

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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}

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Problem 44

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

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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 46

Name each of the following carbonyl compounds.

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Problem 47

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

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Problem 48

Explain the importance of classifying reactions.

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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}

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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}

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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}

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Problem 53

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

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Problem 54

Explain the difference between addition polymerization
and condensation polymerization.

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Problem 55

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

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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}

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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}

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Problem 58

Choose the polymer of each pair that you expect to have
the higher water solubility.

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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?

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Problem 61

Describe the properties of carboxylic acids.

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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}

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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}

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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}

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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}

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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}

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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.

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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}

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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

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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.

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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}

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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)

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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}

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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}

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Problem 79

What is a rate-determining step? (Chapter 16)

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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$)$

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Problem 81

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

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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.

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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?

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Problem 84

When does the drug reach its peak concentration?

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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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