Schaum's Outline of General, Organic, and Biochemistry for Nursing and Allied Health

George Odian, Ira Blei

Chapter 12

Unsaturated Hydrocarbons: Alkenes, Alkynes, Aromatics - all with Video Answers

Educators

Chapter Questions

Problem 1

What is the structural relationship between an alkene and the corresponding alkane (i.e., the alkane with the same number of carbons)?

Kevin Barayuga

Kevin Barayuga

Numerade Educator

Problem 2

What is the relationship between an alkene and a cycloalkane?

Madeline Currie

Madeline Currie

Numerade Educator

Problem 3

Describe the orbitals used by carbon in forming the carbon-carbon double bond in ethene, $\mathrm{C}_2 \mathrm{H}_4$.

Vasu Makani

Numerade Educator

Problem 4

Give the bond angles for $A, B, C$, and $D$ :
FIGURE CAN'T COPY.

Freddie Montague

Freddie Montague

Numerade Educator

Problem 5

How many alkenes exist for the molecular formula $\mathrm{C}_4 \mathrm{H}_8$ ? Show only one structural formula for each constitutional isomer.

Adriano Chikande

Adriano Chikande

Numerade Educator

Problem 6

How many compounds exist for the molecular formula $\mathrm{C}_4 \mathrm{H}_8$ ? Show only one structural formula for each isomer.

Bin Chen

Numerade Educator

Problem 7

Name the following compound by the IUPAC system:
FIGURE CAN'T COPY.

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Problem 8

Is the difference between cis-2-butene and trans-2-butene the same as that between the two conformations of butane shown below?
FIGURE CAN'T COPY.

Bobby Barnes

University of North Texas

Problem 9

What do the following structural formulas represent?
FIGURE CAN'T COPY.

Lottie Adams

Numerade Educator

Problem 10

Are cis and trans isomers possible for all alkene structures?

Sydney Atkins

Numerade Educator

Problem 11

Which of the following exist as a pair of cis and trans isomers? (a) 1,1-dichloro-1-butene, (b) 1,2-dichloroethene, (c) 3-hexene. Show structures of the cis and trans isomers.

Vasu Makani

Numerade Educator

Problem 12

Which of the following exist as cis and trans isomers? (a) 1-methylcyclobutane, (b) $1,1,2$ trimethylcyclopentane, (c) 1,2-dimethylcyclopentane.

Vasu Makani

Numerade Educator

Problem 13

Why is the addition of HCl to 1-butene more complicated than the additions of $\mathrm{Cl}_2$ to 1-butene and $\mathrm{Cl}_2$ or HCl to 2-butene?

Lottie Adams

Numerade Educator

Problem 14

How do we predict which product will be the major product in additions of unsymmetrical reagents such as $\mathrm{H}-\mathrm{Cl}, \mathrm{H}-\mathrm{OH}$, and $\mathrm{H}-\mathrm{OSO}_3 \mathrm{H}$ to unsymmetrical alkenes?

Mary Shields

Numerade Educator

Problem 15

Show the product(s) formed when 2-methyl-1-propene reacts with $\mathrm{H}_2, \mathrm{Cl}_2, \mathrm{HCl}, \mathrm{H}_2 \mathrm{O}$, and $\mathrm{H}_2 \mathrm{SO}_4$.

Catherine Lemar

Catherine Lemar

Numerade Educator

Problem 16

Show how carbocation stability explains Markovnikoff's rule in the addition of HCl to propene.

Mishal Gul

Numerade Educator

Problem 17

Methane, octane, and polyethylene are members of the alkane family. Combustion of methane (gas heating) and octane (liquid-burning engines) are used as sources of energy. In contrast polyethylene is used for producing objects such as milk, food, and detergent bottles. What macroscopic property is responsible for this difference? What molecular-level property determines this difference?

David Collins

Numerade Educator

Problem 18

Complete each of the following reactions by writing the structure of the organic product. If no reaction occurs, write "No Reaction." If there is more than one product, indicate which are the major and which the minor products.
(a) $\mathrm{CH}_3-\mathrm{CH}=\mathrm{CH}_2 \xrightarrow{\mathrm{HCl}}$ ?
(b) $\mathrm{CH}_3-\mathrm{CH}=\mathrm{CH}_2 \xrightarrow{\mathrm{NaOH}}$ ?
(c) $\mathrm{CH}_3-\mathrm{CH}=\mathrm{CH}_2 \xrightarrow{\text { combustion }}$ ?
(d) $\mathrm{CH}_3-\mathrm{CH}=\mathrm{CH}_2 \xrightarrow{\mathrm{H}_2 \mathrm{O}, \mathrm{H}^{+}}$?

Crystal Wang

Numerade Educator

Problem 19

Name the following by the IUPAC system:

$$
\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CH}_2-\mathrm{CH}-\mathrm{C} \equiv \mathrm{C}-\mathrm{CH}_3
$$

Raghvendra Singh

Raghvendra Singh

Numerade Educator

Problem 20

Show the product formed when propyne reacts with excess HCl .

Ronald Prasad

Numerade Educator

Problem 21

Which of the following compounds are aromatic?
FIGURE CAN'T COPY.

Alice .

Numerade Educator

Problem 22

Why do three double bonds alternating with single bonds in a cyclic arrangement have properties very different from alkenes?

Narayan Hari

Numerade Educator

Problem 23

What do each of the following structural drawings represent?

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Problem 24

Name each of the following by the IUPAC system:
FIGURE CAN'T COPY.

Ronald Prasad

Numerade Educator

Problem 25

What is substituting for what in the sulfonation of benzene?

Grigoriy Sereda

Grigoriy Sereda

Numerade Educator

Problem 26

Is the high stability of the aromatic structure evident in other reactions?

Alice .

Numerade Educator

Problem 27

Which of the following are correct molecular formulas? (a) $\mathrm{C}_5 \mathrm{H}_{10}$, (b) $\mathrm{C}_4 \mathrm{H}_8 \mathrm{Br}_{\text {, }}$ (c) $\mathrm{C}_4 \mathrm{H}_7 \mathrm{Br}$.

David Collins

Numerade Educator

Problem 28

For each of the following compounds, what is the hybridization of the carbons indicated by arrows? What are the bond angles about those carbons?

Bhumika Jayee

Numerade Educator

Problem 29

How many alkenes exist for the molecular formula $\mathrm{C}_5 \mathrm{H}_{10}$ ? Show only one structural formula for each constitutional isomer.

Lottie Adams

Numerade Educator

Problem 30

How many constitutional isomers are possible for the molecular formula $\mathrm{C}_5 \mathrm{H}_{10}$ ? Show only one structural formula for each isomer.

Adriano Chikande

Adriano Chikande

Numerade Educator

Problem 31

Name the following compound by the IUPAC system:
FIGURE CAN'T COPY.

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Problem 32

Which of the alkenes in Problem 12.29 exist as separate cis and trans isomers? Show structural formulas for the cis and trans isomers that exist.

Isabella Huang

Numerade Educator

Problem 33

Which of the following exist as separate cis and trans isomers?
FIGURE CAN'T COPY.

Vasu Makani

Numerade Educator

Problem 34

For each of the following pairs of structural drawings, indicate whether the pair represents (1) the same compound, or (2) different compounds which are constitutional isomers, or (3) different compounds which are cis-trans isomers, or (4) different compounds which are not isomers:
FIGURE CAN'T COPY.

Ronald Prasad

Numerade Educator

Problem 35

Give the equation for each of the following reactions. If there is more than one product, indicate which is the major product(s) and which the minor. If there is no reaction, state "No Reaction." (a) 1-Butene +NaOH , (b) 1-methylcyclohexene +HCl , (c) 1,3-butadiene + excess $\mathrm{Cl}_2$, (d) polymerization of 2-methylpropene, (e) oxidation of 2-pentene with hot, acidic $\mathrm{K}_2 \mathrm{Cr}_2 \mathrm{O}_7$, $(f)$ combustion of 2-pentene, $(\mathrm{g})$ 1-methylcyclohexene $+\mathrm{H}_2 \mathrm{O}$ in the presence of an acid catalyst.

Dalton Hilovsky

Dalton Hilovsky

Numerade Educator

Problem 36

Give the equation for the reaction of 2-butyne with HCl . If there is more than one product, indicate which is the major product(s) and which the minor. If there is no reaction, state "No Reaction."

Vasu Makani

Numerade Educator

Problem 37

Which of the following are aromatic?
FIGURE CAN'T COPY.

Alice .

Numerade Educator

Problem 38

For each of the following pairs of structural drawings, indicate whether the pair represents (1) the same compound, or (2) different compounds which are constitutional isomers, or (3) different compounds which are cis-trans isomers, or (4) different compounds which are not isomers:
FIGURE CAN'T COPY.

Ronald Prasad

Numerade Educator

Problem 39

Name each of the following by the IUPAC system:
FIGURE CAN'T COPY.

Ronald Prasad

Numerade Educator

Problem 40

Write equations to show the products formed in each of the following reactions. If no reaction occurs, write "No Reaction." If more than one product is formed, indicate the major and minor products. (a) Benzene +NaOH , (b) benzene $+\mathrm{Cl}_2$, (c) benzene $+\mathrm{Cl}_2+\mathrm{FeCl}_3$, (d) methylbenzene (toluene) $+\mathrm{Cl}_2+$ light or heat, $($ e $)$ methylbenzene (toluene) $+\mathrm{Cl}_2+\mathrm{FeCl}_3$.

Zubair Abdulla

Numerade Educator

Problem 41

For each of the following pairs of structural drawings, indicate whether the pair represents (1) the same compound, or (2) different compounds which are constitutional isomers, or (3) different compounds which are cis-trans isomers, or (4) different compounds which are not isomers:
FIGURE CAN'T COPY.

Ronald Prasad

Numerade Educator

Problem 42

An unknown compound has the molecular formula $\mathrm{C}_5 \mathrm{H}_8$. Based on the molecular formula, what family (families) is (are) possible for the compound? Give an example of each family.
FIGURE CAN'T COPY.

Alice .

Numerade Educator

Problem 43

Indicate the $1^{\circ}, 2^{\circ}, 3^{\circ}$, and $4^{\circ}$ carbons in the following compound:
FIGURE CAN'T COPY.

Bin Chen

Numerade Educator

Problem 44

What is the molecular formula of each of the following compounds?
FIGURE CAN'T COPY.

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Problem 45

An unknown compound is either benzene, cyclohexene, or cyclohexane. Describe how you would determine the identity of the unknown by using simple chemical tests.

Anand Jangid

Numerade Educator

Problem 46

Which of the following exist as a pair of cis and trans isomers? Show structures of the cis and trans isomers. (a) 4-Methyl-2-pentene, (b) 2,4-dimethyl-2-pentene, (c) 4-methyl-2-pentyne, (d) 1,1-dichlorocyclopropane, (e) 1,2-dichlorocyclopropane.

Lottie Adams

Numerade Educator

Problem 47

Place cyclohexane, cyclohexene, and benzene in order of increasing boiling points.

Lashan De Silva

Lashan De Silva

University of Houston

Problem 48

Write equations to show the products formed in each of the following reactions. If no reaction occurs, write "No Reaction." If more than one product is formed, indicate the major and minor products.
FIGURE CAN'T COPY.

Grigoriy Sereda

Grigoriy Sereda

Numerade Educator

Problem 49

Draw structural formulas of the following compounds: (a) 5-chloro-2,4-dimethyl-4-phenyl-2-hexene, (b) 1-bromo-4-t-butylbenzene.

Lottie Adams

Numerade Educator

Problem 50

The acid-catalyzed hydration of propene, i.e., addition of water to propene, yields a mixture of two different products. What are the two products? Write the step-by-step mechanism for the reaction.

Nicole Krahulik

Nicole Krahulik

Numerade Educator