Fundamentals of General, Organic, and Biological Chemistry

John McMurry, David S. Ballantine, Carl A. Hoeger

Chapter 13 Alkenes, Alkynes, and Aromatic Compounds - all with Video Answers

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Chapter Questions

06:34

Problem 1

What are the IUPAC names of the following compounds?

Shahina -

Numerade Educator

12:02

Problem 2

Draw both condensed and line structures corresponding to the following IUPAC names:
(a) 3-Methylhept-1-ene
(b) 4,4 -Dimethylpent-2-yne
(c) 2 -Methylhex -3 -ene
(d) 1,3,3 -Trimethylcyclohexene

Shahina -

Numerade Educator

06:21

Problem 3

What are the IUPAC names of the two alkenes shown in the margin? Redraw each in line structure format.

Shahina -

Numerade Educator

03:29

Which of the following substances exist as can cis-trans isomers? Draw both isomers for those that do.
(a) 2,3 -Dimethylpent- 2 -ene (condensed structures only)
(b) 2 -Methylhex- 2 -ene (both condensed and line structures)
(c) Hex-2-ene (line structures only)

Vasu Makani

Numerade Educator

06:12

Problem 5

Draw both the condensed and line structures for the cis and trans isomers of 3,4 -dimethylhex-3-ene.

Shahina -

Numerade Educator

03:53

Problem 6

Name the compounds shown below, including the appropriate cis- or trans- prefix. Redraw each in line structure format.

Vasu Makani

Numerade Educator

06:47

Problem 7

Classify the following reactions as an addition, elimination, or substitution:
(a) $\mathrm{CH}_{3} \mathrm{Br}+\mathrm{NaOH} \longrightarrow \mathrm{CH}_{3} \mathrm{OH}+\mathrm{NaBr}$
(b) $\mathrm{H}_{2} \mathrm{C}=\mathrm{CH}_{2}+\mathrm{HCl} \longrightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}$
(c) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Br} \longrightarrow \mathrm{H}_{2} \mathrm{C}=\mathrm{CH}_{2}+\mathrm{HBr}$

Shahina -

Numerade Educator

00:32

Problem 8

Many biological transformations can be simply classified as additions, eliminations, or substitutions. How would you classify the following reactions?
(a) Fumaric acid to malic acid (found in the citric acid cycle, Section 21.8 )
(b) 2-Phosphoglyceric acid to phosphoenolpyruvic acid (found in glycolysis, Section 22.3)

Maryam Shahid

Numerade Educator

03:07

Problem 9

Write the structures of the products from the following hydrogenation reactions:

Vasu Makani

Numerade Educator

03:02

Problem 10

What products would you expect from the following halogenation reactions?

Vasu Makani

Numerade Educator

02:01

Problem 11

Draw all possible products formed when 2 -methylbut-2-ene undergoes addition with HCl. Label them as being either the major or the minor product.

Vasu Makani

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01:45

Problem 12

What major products do you expect from the following reactions?

Vasu Makani

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01:56

Problem 13

In the following addition reactions, are the given alkyl halides obtained as the major products? Give a reason for your answer.
(a) 3-Chloro-3-ethylpentane from addition of $\mathrm{HCl}$ to 3 -ethylpent- 2 -ene
(b)

Bryce Werts

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02:13

Problem 14

What product do you expect from the following reaction? Draw your answer in both condensed and line structure formats.

Vasu Makani

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03:55

Problem 15

What products do you expect from the following hydration reactions? Label them as major and minor if more than one is formed.

Arun Bana

Numerade Educator

01:56

Problem 16

Draw the structures of the two different alkenes from which 3 -methylpentan- 3 -ol, shown in the margin, can be made. Draw them in both condensed and line format.

Vasu Makani

Numerade Educator

04:53

Problem 17

The structure of vinyl acetate is shown below (the partial structure $\mathrm{H}_{2} \mathrm{C}=\mathrm{CH}-$ is known as a vinyl group). When polymerized it produces poly(vinyl acetate), a polymer used for the springy soles in running shoes. Draw the structure of the polymer obtained if three vinyl acetate units underwent polymerization.

Nicholas Sacco

Numerade Educator

00:31

Problem 18

Polychlorotrifluoroethylene (PCTFE (Kel-F)) is a polymer that has the lowest water vapor transmission rate of any plastic, making it an excellent moisture barrier. It can also be used for injection molding of plastic items, while polytetrafluoroethylene (PTFE (Teflon)) cannot. Given the monomer shown below, draw a representative structure for PCTFE.

Ronald Prasad

Numerade Educator

01:48

Problem 19

What are the IUPAC names for the following compounds?

Vasu Makani

Numerade Educator

06:29

Problem 20

Draw structures corresponding to the following names (refer to Table 13.2 if necessary):
(a) $m$ -Chloronitrobenzene
(b) $o$ -Nitrotoluene
(c) $p$ -Methylaniline
(d) $p$ -Nitrophenol

Shahina -

Numerade Educator

02:47

Problem 21

Name the following compounds $(\mathrm{red}=\mathrm{O},$ blue $=\mathrm{N},$ brown $=\mathrm{Br})$

Vasu Makani

Numerade Educator

01:36

Problem 22

What products will be formed when toluene is reacted with the reagents shown here?
(a) $\mathrm{Br}_{2}$ and $\mathrm{FeBr}_{3}$
(b) $\mathrm{HNO}_{3}$ and $\mathrm{H}_{2} \mathrm{SO}_{4}$ catalyst
(c) $\mathrm{SO}_{3}$ in $\mathrm{H}_{2} \mathrm{SO}_{4}$

Simran Chopra

Numerade Educator

02:30

Problem 23

Reaction of $\mathrm{Br}_{2}$ and $\mathrm{FeBr}_{3}$ with phenol can lead to three possible substitution products. Show the structure of each and name them.

Shahina -

Numerade Educator

09:59

Problem 24

Name the following alkenes, and predict the products of their reaction with (1) $\mathrm{HBr},$ (2) $\mathrm{H}_{2} \mathrm{O},$ and (3) an acid catalyst.

Anupa Sharad Medhekar

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02:18

Problem 25

Name the following alkynes:

Vasu Makani

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02:17

Problem 26

Give IUPAC names for the following substances (red $=0,$ brown $=\mathrm{Br}$ ):

Vasu Makani

Numerade Educator

04:28

Problem 27

Draw the product from reaction of the following substances with (1) $\mathrm{Br}_{2}$ and $\mathrm{FeBr}_{3}$ and (2) $\mathrm{SO}_{3}$ and $\mathrm{H}_{2} \mathrm{SO}_{4}$ catalyst $($ red $=0)$

Matthew Lueckheide

Numerade Educator

01:54

Problem 28

Alkynes undergo hydrogenation to give alkanes, just as alkenes do. Draw and name the products that would result from hydrogenation of the alkynes shown in Problem 13.25 .

Vasu Makani

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01:01

Problem 29

We saw in Section 13.8 that benzene can be represented by either of two resonance forms, which differ in the positions of the double bonds in the aromatic ring. Naphthalene, a polycyclic aromatic compound, can be represented by three forms with different double-bond positions. Draw all three structures, showing the double bonds in each (the following numbered skeletal structure of naphthalene shows only the connections among atoms).

Simran Chopra

Numerade Educator

05:31

Problem 30

(a) What do the terms saturated and unsaturated mean?
(b) Draw an example of a saturated four carbon compound and an unsaturated four carbon compound.

Shahina -

Numerade Educator

01:59

Problem 31

(a) What does the term "aromatic" refer to when discussing organic molecules?
(b) What is resonance and why is it important in aromatic compounds?

Simran Chopra

Numerade Educator

02:50

Problem 32

What family-name endings are used for alkenes, alkynes, and substituted benzenes?

Shahina -

Numerade Educator

01:20

Problem 33

What prefixes are used in naming the following?
(a) A 1,3 -disubstituted benzene
(b) A 1,4 -disubstituted benzene

Simran Chopra

Numerade Educator

05:21

Problem 34

Write structural formulas for compounds that meet the following descriptions:
(a) A 6-carbon alkene whose longest chain is 4 carbons in length (three possibilities)
(b) An alkyne with 5 carbons total (three possibilities)
(c) A monosubstituted benzene with a total of 8 carbons (one possibility)
(d) A disubstituted benzene with a total of 8 carbons (three possibilities)

Ricajoy Montero

Numerade Educator

05:21

Problem 35

Write structural formulas for compounds that meet the following descriptions:
(a) An alkene, $\mathrm{C}_{6} \mathrm{H}_{12}$, that cannot have cis-trans isomers and whose longest chain is 5 carbons long
(b) An alkene with a chemical formula of $\mathrm{C}_{10} \mathrm{H}_{12}$ that has cis-trans isomers and contains a benzene ring.

Ricajoy Montero

Numerade Educator

08:11

Problem 36

What are the IUPAC names of the following compounds?

Shahina -

Numerade Educator

02:04

Problem 37

Give IUPAC names for the following aromatic compounds:

Vasu Makani

Numerade Educator

05:53

Problem 38

Draw structures corresponding to the following IUPAC names:
(a) trans-Pent- 2 -ene
(b) trans-3,4-Dimethylhex-3-ene
(c) 2-Methylbuta-1,3-diene
(d) trans-Hept-3-ene
(e) $p$ -Nitrotoluene
(f) $o$ -Chlorophenol
(g) 1,2-Dimethylcyclobutene
(h) 3,3 -Diethyl-6-methylnon-4-ene

Anand Jangid

Numerade Educator

06:11

Problem 39

Draw structures corresponding to the following names:
(a) Aniline
(b) Phenol
(c) $o$ -Xylene
(d) 2,4,6 -Trinitrobenzene
(e) $p$ -Chlorobenzoic acid
(f) $m$ -Nitroaniline
(g) $o$ -Chlorobenzaldehyde
(h) Anisole (methoxybenzene)

Shahina -

Numerade Educator

04:43

Problem 40

Seven alkynes have the formula $\mathrm{C}_{6} \mathrm{H}_{10}$. Draw them, using line structures.

Shahina -

Numerade Educator

01:58

Problem 41

Draw and name all phenols with the formula $\mathrm{C}_{7} \mathrm{H}_{8} \mathrm{O}$.

Vasu Makani

Numerade Educator

01:05

Problem 42

When ethylbenzene is reacted with nitric acid, three possible benzenes containing both a nitro group and an ethyl group are obtained. Draw and name them.

Simran Chopra

Numerade Educator

02:17

Problem 43

There are four different pentenes having the following general structure:
The four differ only in the placement of the double bond. Draw and name all four. Ignore cis-trans isomers.

Anand Jangid

Numerade Educator

01:47

Problem 44

What requirement(s) must be met for an alkene to show cis-trans isomerism?

Shahina -

Numerade Educator

00:53

Problem 45

Why do alkynes not show cis-trans isomerism?

Simran Chopra

Numerade Educator

03:31

Problem 46

Draw line structures for the following alkenes. Which can exist as cis-trans isomers? For those that can, draw both isomers.
(a) 2-Methyloct- 2 -ene
(b) Hept- 3 -ene
(c) 3,4 -Dimethylhex-3-ene

Shahina -

Numerade Educator

02:08

Problem 47

Which compound(s) in Problem 13.43 can exist as cistrans isomers? Label each as being either a symmetrically or unsymmetrically substituted alkene.

Freddie Montague

Numerade Educator

02:40

Problem 48

Draw structures of the following compounds:
(a) cis-Hept-3-ene
(b) cis-4-Methylpent-2-ene
(c) trans-2,5-Dimethylhex-3-ene

Vasu Makani

Numerade Educator

01:22

Problem 49

Each of the following has a cis or trans isomeric form. Draw it.

Vasu Makani

Numerade Educator

02:45

Problem 50

Which of the following pairs are isomers, and which are identical?

Shahina -

Numerade Educator

00:49

Problem 51

Draw the other cis-trans isomer for the following molecules:

Maryam Shahid

Numerade Educator

03:04

Problem 52

What is the difference between a substitution reaction and an addition reaction?

Nicholas Sacco

Numerade Educator

01:56

Problem 53

Give an example of an addition reaction.

Shahina -

Numerade Educator

01:14

Problem 54

If 2 -methylpent- 2 -ene were converted into hex-1-ene, what kind of reaction would that be?

Vasu Makani

Numerade Educator

01:07

Problem 55

If bromocyclohexane were converted into cyclohexene, what kind of reaction would that be?

Vasu Makani

Numerade Educator

01:19

Problem 56

Identify the type of reaction for the following:

Vasu Makani

Numerade Educator

00:41

Problem 57

Identify the type of reaction for the following:

Maryam Shahid

Numerade Educator

02:21

Problem 58

Write equations for the reaction of pent- 2 -ene with the following:
(a) $\mathrm{H}_{2}$ and $\mathrm{Pd}$ catalyst
(b) $\mathrm{Br}_{2}$
(c) $\mathrm{HCl}$
(d) $\mathrm{H}_{2} \mathrm{O}$ and $\mathrm{H}_{2} \mathrm{SO}_{4}$ catalyst

Simran Chopra

Numerade Educator

02:43

Problem 59

Write equations for the reaction of 1 -methylcyclohexene with the reagents shown in Problem 13.58 .

Vasu Makani

Numerade Educator

04:34

Problem 60

What alkene could you use to make the following products? Draw the structure of the alkene, and tell what other reagent is also required for the reaction to occur.

Anish Wadhwa

Numerade Educator

01:56

Problem 61

2,2,3,3 -Tetrabromopentane can be prepared by an addition reaction of excess $\mathrm{Br}_{2}$ with an alkyne. Draw the structure of the alkyne and name it.

Simran Chopra

Numerade Educator

01:55

Problem 62

4-Methylpent-1-yne reacts with HBr in a 1:1 molar ratio to yield two different addition products, both being bromopentenes and having the chemical formula $\mathrm{C}_{5} \mathrm{H}_{9} \mathrm{Br}$. Draw the structures of two possible products.

Anand Jangid

Numerade Educator

00:34

Problem 63

Polyvinylpyrrolidone (PVP) is often used in hair sprays to hold hair in place. Draw a few units of the PVP polymer. The vinylpyrrolidone monomer unit has the following structure:

Ly Tran

Numerade Educator

00:52

Problem 64

Saran, used as a plastic wrap for foods, is a polymer with the following structure. What is the monomer unit of Saran?

Simran Chopra

Numerade Educator

03:14

Problem 65

For each of the following reagents, decide whether chlorobenzene will react with it or not, and, if it does, draw and name the products expected from the reaction.
(a) $\mathrm{Br}_{2}$ and $\mathrm{FeBr}_{3}$
(b) $\mathrm{HBr}$
(c) $\mathrm{HNO}_{3}$ and $\mathrm{H}_{2} \mathrm{SO}_{4}$ catalyst

Anand Jangid

Numerade Educator

06:01

Problem 66

Write equations for the reaction of $p$ -dichlorobenzene with the following:
(a) $\mathrm{Br}_{2}$ and $\mathrm{FeBr}_{3}$
(b) $\mathrm{HNO}_{3}$ and $\mathrm{H}_{2} \mathrm{SO}_{4}$ catalyst
(c) $\mathrm{H}_{2} \mathrm{SO}_{4}$ and $\mathrm{SO}_{3}$
(d) $\mathrm{Cl}_{2}$ and $\mathrm{FeCl}_{3}$

Shahina -

Numerade Educator

01:25

Problem 67

Aromatic compounds do not normally react with hydrogen in the presence of a palladium catalyst but will if very high pressures ( 200 atm) and high temperatures are used. Under these conditions, toluene adds three molecules of $\mathrm{H}_{2}$ to give an alkane addition product. What is a likely structure for the product?

Anand Jangid

Numerade Educator

02:23

Problem 68

The explosive trinitrotoluene (TNT) is made by carrying out three successive nitration reactions on toluene. If these nitrations only occur in the ortho and para positions relative to the methyl group, what is the structure of TNT?

Shahina -

Numerade Educator

01:02

Problem 69

Salicylic acid (o-hydroxybenzoic acid) is used as starting material to prepare aspirin. Draw the structure of salicylic acid.

Simran Chopra

Numerade Educator

08:51

Problem 70

The following names are incorrect by IUPAC rules. Draw the structures represented by the following names, and write their correct names. Label each as being symmetrically or unsymmetrically substituted.
(a) 2-Methyl-4-hexene
(b) 1,3 -Dimethyl-1-hexyne
(c) 2-Isopropyl-1-propene
(d) 1,4,6 -Trinitrobenzene
(e) 1,2 -Dimethyl-3-cyclohexene
(f) 3-Methyl- 2,4 -pentadiene

Shahina -

Numerade Educator

02:35

Problem 71

Which of the compounds in Problem 13.70 are capable of cis-trans isomerism? Draw each isomer.

Vasu Makani

Numerade Educator

00:59

Problem 72

Assume that you have two unlabeled bottles, one with cyclohexane and one with cyclohexene. How could you tell them apart by carrying out chemical reactions?

Shahina -

Numerade Educator

01:54

Problem 73

Assume you have two unlabeled bottles, one with cyclohexene and one with benzene. How could you tell them apart by carrying out chemical reactions?

Anand Jangid

Numerade Educator

01:06

Problem 74

The compound $p$ -dichlorobenzene has been used as an insecticide. Draw its structure.

Shahina -

Numerade Educator

02:08

Problem 75

Menthene, a compound found in mint plants, has the formula $\mathrm{C}_{10} \mathrm{H}_{18}$ and the IUPAC name 1 -isopropyl4-methylcyclohexene. What is the structure of menthene?

Shahina -

Numerade Educator

01:08

Problem 76

Cinnamaldehyde, the pleasant-smelling substance found in cinnamon oil, has the following structure:

Shahina -

Numerade Educator

02:05

Problem 77

Predict the products of the following reactions:

Grigoriy Sereda

Numerade Educator

02:59

Problem 78

Two products are possible when pent-2-ene is treated with HBr. Write the structures of the possible products, and explain why they are made in about equal amounts.

Shahina -

Numerade Educator

03:58

Problem 79

Ocimene, a compound isolated from the herb basil, has three double bonds and the IUPAC name 3,7 -dimethylocta1,3,6 -triene.
(a) Draw its structure.
(b) Draw the structure of the compound formed if enough HBr is added to react with all the double bonds in ocimene.

Anand Jangid

Numerade Educator

04:25

Problem 80

Describe how you could prepare the following compound from an alkene. Draw the formula of the alkene, name it, and list the inorganic reactants or catalysts needed for the conversion.

Niamat Khuda

Numerade Educator

02:35

Problem 81

Which of the following compounds are capable of cis-trans isomerism?

Vasu Makani

Numerade Educator

02:01

Problem 82

Why do you suppose small-ring cycloalkenes like cyclohexene do not exist as cis-trans isomers, whereas large ring cycloalkenes like cyclodecene do show isomerism?

Anand Jangid

Numerade Educator

03:59

Problem 83

"Superglue" is an alkene polymer made from the monomer unit.

Dan Cash

Numerade Educator

02:21

Problem 84

Draw all possible $\mathrm{C}_{5} \mathrm{H}_{10}$ alkene isomers having a longest chain of four carbons and a methyl group. (Hint: Adapt the method described in Worked Example 12.12 to arrive at your answers.)

Simran Chopra

Numerade Educator