Introduction to General, Organic and Biochemistry

Frederick A. Bettelheim, William H. Brown, Mary K. Campbell

Chapter 14

Alcohols, Ethers, and Thiols - all with Video Answers

Educators

Chapter Questions

Problem 1

Write the IUPAC name of each alcohol.

Ly Tran

Ly Tran

Numerade Educator

Problem 2

Classify each alcohol as primary, secondary, or tertiary.

Vasu Makani

Numerade Educator

Problem 3

Draw structural formulas for the alkenes formed by the acid-catalyzed dehydration of each alcohol. For each part, predict which alkene will be the major product.
(a) $2-$ Methyl-2-butanol
(b) $1-$ Methylcyclopentanol

Vasu Makani

Numerade Educator

Problem 4

Acid-catalyzed dehydration of 2-methylcyclohexanol gives predominantly Compound $\mathrm{C}\left(\mathrm{C}_{7} \mathrm{H}_{12}\right)$. Treatment of Compound $\mathrm{C}$ with water in the presence of sulfuric acid gives Compound $\mathrm{D}\left(\mathrm{C}_{7} \mathrm{H}_{14} \mathrm{O}\right) .$ Propose structural for mulas for Compounds C and D.

Vasu Makani

Numerade Educator

Problem 5

Draw the product formed by oxidation of each of the following alcohols with potassium dichromate.
(a) Cyclohexanol
(b) $2-$ Pentanol

Ronald Prasad

Numerade Educator

Problem 6

Write the common name for each ether.

Colton Wang

Numerade Educator

Problem 7

Write the IUPAC name of each thiol.

Kevin Barayuga

Numerade Educator

Problem 8

Answer true or false.
(a) The functional group of an alcohol is the $-\mathrm{OH}$ (hydroxyl) group.
(b) The parent name of an alcohol is the name of the longest carbon chain that contains the $-\mathrm{OH}$ group.
(c) A primary alcohol contains one $-$ OH group, and a tertiary alcohol contains three - OH groups.
(d) In the IUPAC system, the presence of three $-$ OH groups is shown by the ending -triol.
(e) A glycol is a compound that contains two $-\mathrm{OH}$ groups. The simplest glycol is ethylene glycol, $\mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{OH}$
(f) Because of the presence of an $-$ OH group, all alcohols are polar compounds.
(g) The boiling points of alcohols increase with in creasing molecular weight.
(h) The solubility of alcohols in water increases with increasing molecular weight.

Nicholas Sacco

Numerade Educator

Problem 9

What is the difference in structure between a primary, a secondary, and a tertiary alcohol?

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 10

Which of the following are secondary alcohols?

Kevin Barayuga

Numerade Educator

Problem 11

Which of the alcohols in Problem $14-10$ are primary? Which are tertiary?

Vasu Makani

Numerade Educator

Problem 12

Write the IUPAC name of each compound.

Susan Hallstrom

Susan Hallstrom

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Problem 13

Draw a structural formula for each alcohol.
(a) Isopropyl alcohol
(b) Propylene glycol
(c) $5-$ Methyl-2-hexanol
(d) 2 -Methyl-2-propyl-1,3-propanediol
(e) $1-$ Octanol
(f) 3,3 -Dimethylcyclohexanol

Kevin Barayuga

Numerade Educator

Problem 14

Draw a structural formula for each of the following alcohols.
(a) Isobutyl alcohol
(b) 1,4 -Butanediol
(c) 5 -Methyl-1-hexanol
(d) 1,3 -Pentanediol
(e) $\operatorname{trans}-1,4-$ Cyclohexanediol
(f) $1-$ Chloro- 2 -propanol

Vasu Makani

Numerade Educator

Problem 15

Both alcohols and phenols contain an - OH group. What structural feature distinguishes these two classes of compounds? Illustrate your answer by drawing the structural formulas of a phenol with six carbon atoms and an alcohol with six carbon atoms.

Vasu Makani

Numerade Educator

Problem 16

Name the functional groups in each compound.

Colton Wang

Numerade Educator

Problem 17

Explain in terms of noncovalent interactions why the low-molecular-weight alcohols are soluble in water but the low-molecular-weight alkanes and alkynes are not.

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 18

Explain in terms of noncovalent interactions why the low-molecular-weight alcohols are more soluble in water than the low-molecular-weight ethers.

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 19

Why does the water solubility of low-molecularweight alcohols decrease as molecular weight increases?

Vasu Makani

Numerade Educator

Problem 20

Show hydrogen bonding between methanol and water in the following ways.
(a) Between the oxygen of methanol and a hydrogen of water
(b) Between the hydrogen of methanol's OH group and the oxygen of water

Kevin Barayuga

Numerade Educator

Problem 21

Show hydrogen bonding between the oxygen of diethyl ether and a hydrogen of water.

Kevin Barayuga

Numerade Educator

Problem 22

Arrange these compounds in order of increasing boiling point. Values in $^{\circ} \mathrm{C}$ are $-42,78,117,$ and 198
(a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}$
(b) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}$
$(\mathrm{c}) \mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{OH}$
(d) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{3}$

Vasu Makani

Numerade Educator

Problem 23

Arrange these compounds in order of increasing boiling point. Values in $^{\circ} \mathrm{C}$ are 0,35 , and 97 .
(a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}$
(b) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{2} \mathrm{CH}_{3}$
(c) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}$

Vasu Makani

Numerade Educator

Problem 24

2-Propanol (isopropyl alcohol) is commonly used as rubbing alcohol to cool the skin. 2-Hexanol, also a liquid, is not suitable for this purpose. Why?

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 25

Explain why glycerol is much thicker (more viscous) than ethylene glycol, which in turn is much more viscous than ethanol.

Nicholas Sacco

Numerade Educator

Problem 26

From each pair, select the compound that is more soluble in water.

Kevin Barayuga

Numerade Educator

Problem 27

Arrange the compounds in each set in order of decreasing solubility in water.
(a) Ethanol, butane, and diethyl ether
(b) $1-$ Hexanol, 1,2 -hexanediol, and hexane

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 28

Give the structural formula of an alkene or alkenes from which each alcohol can be prepared.
(a) $2-$ Butanol
(b) $1-$ Methylcyclohexanol
(c) 3 -Hexanol
(d) 2 -Methyl-2-pentanol
(e) Cyclopentanol

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 29

Answer true or false.
(a) The two most important reactions of alcohols are their acid-catalyzed dehydration to give alkenes and their oxidation to aldehydes, ketones, and carboxylic acids.
(b) The acidity of alcohols is comparable to that of water.
(c) Water-insoluble alcohols and water-insoluble phenols react with strong bases to give watersoluble salts.
(d) Acid-catalyzed dehydration of cyclohexanol gives cyclohexane.
(e) When the acid-catalyzed dehydration of an alkene can yield isomeric alkenes, the alkene with the greater number of hydrogens on the carbons of the double bond generally predominates.
(f) The acid-catalyzed dehydration of 2-butanol gives predominantly 1-butene.
(g) The oxidation of a primary alcohol gives either an aldehyde or a carboxylic acid depending on experimental conditions.
(h) The oxidation of a secondary alcohol gives a carboxylic acid.
(i) Acetic acid, $\mathrm{CH}_{3} \mathrm{COOH}$, can be prepared from ethylene, $\mathrm{CH}_{2}=\mathrm{CH}_{2}$, by treatment of ethylene with $\mathrm{H}_{2} \mathrm{O} / \mathrm{H}_{2} \mathrm{SO}_{4}$, followed by treatment with $\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7} / \mathrm{H}_{2} \mathrm{SO}_{4}$
(j) Treatment of propene, $\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CH}_{2}$, with $\mathrm{H}_{2} \mathrm{O} /$
$\mathrm{H}_{2} \mathrm{SO}_{4}$ followed by treatment with $\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{2} / \mathrm{H}_{2} \mathrm{SO}_{4}$
gives propanoic acid, $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH}$

Sana Riaz

Numerade Educator

Problem 30

Show how to distinguish between cyclohexanol and cyclohexene by a simple chemical test. Tell what you would do, what you would expect to see, and how you would interpret your observation.

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 31

Compare the acidity of alcohols and phenols, which are both classes of organic compounds that contain an $-$ OH group.

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 32

Both 2,6 -diisopropylcyclohexanol and the intravenous anesthetic Propofol are insoluble in water. Show how these two compounds can be distinguished by their reaction with aqueous sodium hydroxide.

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 33

Write equations for the reaction of 1 -butanol, a primary alcohol, with these reagents.
(a) $\mathrm{H}_{2} \mathrm{SO}_{4},$ heat
(b) $\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}, \mathrm{H}_{2} \mathrm{SO}_{4}$

Kevin Barayuga

Numerade Educator

Problem 34

Write equations for the reaction of 2 -butanol with these reagents.
(a) $\mathrm{H}_{2} \mathrm{SO}_{4},$ heat
(b) $\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}, \mathrm{H}_{2} \mathrm{SO}_{4}$

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 35

Write equations for the reaction of each of the following compounds with $\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7} / \mathrm{H}_{2} \mathrm{SO}_{4}$
(a) $1-$ Octanol
(b) $1,4-$ Butanediol

Kevin Barayuga

Numerade Educator

Problem 36

Show how to convert cyclohexanol to these compounds.
(a) Cyclohexene
(b) Cyclohexane
(c) Cyclohexanone
(d) Bromocyclohexane

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 37

Show reagents and experimental conditions to synthesize each compound from 1-propanol.

Nicholas Sacco

Numerade Educator

Problem 38

Show how to convert this alcohol to compounds
(a) and (b).

Kevin Barayuga

Numerade Educator

Problem 39

Name two important alcohols derived from ethylene and give two important uses of each.

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 40

Name two important alcohols derived from propene and give two important uses of each.

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 41

Answer true or false.
(a) Ethanol and dimethyl ether are constitutional isomers.
(b) The solubility of low-molecular-weight ethers in water is comparable to that of low-molecularweight alcohols in water
(c) Ethers undergo many of the same reactions that alcohols do.

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 42

Write the common name for each ether.

Colton Wang

Numerade Educator

Problem 43

Write the common name for each of the following ethers.

Colton Wang

Numerade Educator

Problem 44

Answer true or false.
(a) The functional group of a thiol is the $-\mathrm{SH}$ (sulfhydryl) group.
(b) The parent name of a thiol is the name of the longest carbon chain that contains the $-$ SH group.
(c) The $S-H$ bond is nonpolar covalent.
(d) The acidity of ethanethiol is comparable to that of phenol.
(e) Both phenols and thiols are classified as weak acids.
(f) The most common biological reaction of thiols is their oxidation to disulfides.
(g) The functional group of a disulfide is the $-\mathrm{S}-\mathrm{S}-$ group.
(h) Conversion of a thiol to a disulfide is a reduction reaction.

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 45

Write the IUPAC name of each thiol.

Kevin Barayuga

Numerade Educator

Problem 46

Write the common name for each thiol in Problem $14-45$.

Vasu Makani

Numerade Educator

Problem 47

Following are structural formulas for 1 -butanol and 1-butanethiol. One of these compounds has a boiling point of $98^{\circ} \mathrm{C}$ and the other has a boiling point of $117^{\circ} \mathrm{C} .$ Which compound has which boiling point?
$$\begin{array}{cc}\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH} & \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{SH} \\1-\text { Butanol } & 1 \text { -Butanethiol }\end{array}$$

Vasu Makani

Numerade Educator

Problem 48

Explain why methanethiol, $\mathrm{CH}_{3} \mathrm{SH}$, has a lower boiling point $\left(6^{\circ} \mathrm{C}\right)$ than methanol, $\mathrm{CH}_{3} \mathrm{OH}\left(65^{\circ} \mathrm{C}\right)$, even though methanethiol has a higher molecular weight.

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 49

Answer true or false.
(a) Today, the major carbon sources for the synthesis of methanol are coal and methane (natural gas), both nonrenewable resources.
(b) Today the major carbon sources for the synthesis of ethanol are petroleum and natural gas, both nonrenewable resources.
(c) Intermolecular acid-catalyzed dehydration of ethanol gives diethyl ether.
(d) Conversion of ethylene to ethylene glycol involves oxidation to ethylene oxide, followed by acid-catalyzed hydration (addition of water) to ethylene oxide.
(e) Ethylene glycol is soluble in water in all proportions.
(f) A major use of ethylene glycol is as automobile antifreeze.

Rabeya Zahid

Numerade Educator

Problem 50

(Chemical Connections 14 A) As stated in the $\mathrm{CC}$, "Hydrogen bonds have directionality in that the donor and acceptor groups must be oriented appropriately with respect to each other for hydrogen bonding to occur." Describe the directionality of hydrogen bonding observed in figure ( $b$ ) of the CC.

Rabeya Zahid

Numerade Educator

Problem 51

(Chemical Connections 14B) When was nitroglycerin discovered? Is this substance a solid, a liquid, or a gas?

Vasu Makani

Numerade Educator

Problem 52

(Chemical Connections $14 \mathrm{B}$ ) What was Alfred Nobel's discovery that made nitroglycerin safer to handle?

Vasu Makani

Numerade Educator

Problem 53

(Chemical Connections $14 \mathrm{B}$ ) What is the relationship between the medical use of nitroglycerin to relieve the sharp chest pains (angina) associated with heart disease and the gas nitric oxide, NO?

Vasu Makani

Numerade Educator

Problem 54

(Chemical Connections $14 \mathrm{C}$ ) What is the color of dichromate ion, $\mathrm{Cr}_{2} \mathrm{O}_{7}^{2-} ?$ What is the color of chromium(III) ion, $\mathrm{Cr}^{3+}$ ? Explain how the conversion of one to the other is used in breathalcohol screening.

Rabeya Zahid

Numerade Educator

Problem 55

(Chemical Connections $14 \mathrm{C}$ ) The legal definition of being under the influence of alcohol is based on blood alcohol content. What is the relationship between breath alcohol content and blood alcohol content?

Rabeya Zahid

Numerade Educator

Problem 56

(Chemical Connections 14 D) What does it mean to say that ethylene oxide is a highly strained molecule?

Rabeya Zahid

Numerade Educator

Problem 57

(Chemical Connections $14 \mathrm{E}$ ) What are the advantages and disadvantages of using diethyl ether as an anesthetic?

Rabeya Zahid

Numerade Educator

Problem 58

(Chemical Connections $14 \mathrm{E}$ ) Show that enflurane and isoflurane are constitutional isomers.

Vasu Makani

Numerade Educator

Problem 59

(Chemical Connections $14 \mathrm{E}$ ) Would you expect enflurane and isoflurane to be soluble in water? Would you expect them to be soluble in organic solvents such as hexane?

Sana Riaz

Numerade Educator

Problem 60

Write a balanced equation for the complete combustion of ethanol, the alcohol blended with gasoline to produce E85.

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 61

Knowing what you do about electronegativity, the polarity of covalent bonds, and hydrogen bonding, would you expect an $\mathrm{N}-\mathrm{H}-\mathrm{N}$ hydrogen bond to be stronger than, the same strength as, or weaker than an $\mathrm{O}-\mathrm{H}-\mathrm{O}$ hydrogen bond?

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 62

Draw structural formulas and write IUPAC names for the eight isomeric alcohols with the molecular formula $\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}$.

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 63

Draw structural formulas and write common names for the six isomeric ethers with the molecular for mula $\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}$.

Vasu Makani

Numerade Educator

Problem 64

Explain why the boiling point of ethylene glycol $\left(198^{\circ} \mathrm{C}\right)$ is so much higher than that of 1 -propanol $\left(97^{\circ} \mathrm{C}\right)$, even though their molecular weights are about the same.

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 65

Following is a structural formula for Erythromycin A, a macrolactone (macrolide) antibiotic.
(a) How many hydroxyl groups are present? Classify each as primary $\left(1^{\circ}\right),$ secondary $\left(2^{\circ}\right),$ or tertiary $\left(3^{\circ}\right)$
(b) How many amine groups are present? Classify each as primary $\left(1^{\circ}\right),$ secondary $\left(2^{\circ}\right),$ or tertiary $\left(3^{\circ}\right)$
(c) Locate the ester group within the large 15 -member ring.
(d) Four of the hydroxyl groups within Erythromycin A are involved in intramolecular (internal) hydrogen bonds. One of these is pointed out on the structural formula. Note that this hydrogen bond creates a five-membered ring. Locate the other three intramolecular hydrogen bonds and specify the size of the ring created by each.

Noah Boudrie

Numerade Educator

Problem 66

1,4-Butanediol, hexane, and 1-pentanol have similar molecular weights. Their boiling points, arranged from lowest to highest, are $69^{\circ} \mathrm{C}, 138^{\circ} \mathrm{C}$ and $230^{\circ} \mathrm{C} .$ Which compound has which boiling point?

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 67

Of the three compounds given in Problem $14-66,$ one is insoluble in water, another has a solubility of $2.3 \mathrm{g} / 100 \mathrm{g}$ water, and one is infinitely soluble in water. Which compound has which solubility?

Vasu Makani

Numerade Educator

Problem 68

Each of the following compounds is a common organic solvent. From each pair of compounds, select the solvent with the greater solubility in water.
(a) $\mathrm{CH}_{2} \mathrm{Cl}_{2}$ or $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}$
(b) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{2} \mathrm{CH}_{3}$ or $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}$

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 69

Show how to prepare each compound from 2-methyl-1-propanol.
(a) $2-$ Methylpropene
(b) 2 -Methyl-2-propanol
(c) 2 -Methylpropanoic acid, $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCOOH}$

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 70

Show how to prepare each compound from 2-methylcyclohexanol.

Nicholas Sacco

Numerade Educator

Problem 71

The mechanism of the acid-catalyzed dehydration of an alcohol to an alkene is the reverse of the acidcatalyzed hydration of an alkene. The dehydration mechanism occurs by the following three steps. Step 1: Add a proton. Step 2: Break a bond to form stable molecules or ions. Step 3: Take away a proton. These three steps are illustrated here by the dehydration of 2 -butanol to give 2 -butene. Use curved arrows to show the flow of electrons in each step; that is, show how each bond-making or bond-breaking step occurs.

Nicholas Sacco

Numerade Educator

Problem 72

Use the reactions we learned in Chapter 12 and this chapter to show how to bring about the following chemical transformations. Some transformations will require only one step. Others will require two or more steps.

Nicholas Sacco

Numerade Educator

Problem 73

Lipoic acid is a growth factor for many bacteria and protozoa and an essential component of several enzymes involved in human metabolism.
(a) Name the two functional groups in lipoic acid.
(b) At one stage in its function in human metabolism, the disulfide bond of lipoic acid is reduced to two thiol groups. Draw a structural formula for this reduced form of lipoic acid.

Kendrick Buford

Kendrick Buford

Numerade Educator

Problem 74

Following is a structural formula for the amino acid cysteine:
(a) Name the three functional groups in cysteine.
(b) In the human body, cysteine is oxidized to cystine, a disulfide. Draw a structural formula for cystine.

Colton Wang

Numerade Educator

Problem 75

As we will see in Chapter $16,$ the carbonyl group of aldehydes and ketones reacts with water to form a compound called a hydrate. The hydration of a carbonyl group is catalyzed by acid. Formaldehyde, for example, reacts as shown below. When dissolved in water, formaldehyde exists almost entirely as its hydrate. This aqueous solution is given the name formalin.
The mechanism for this acid-catalyzed hydration is similar to the mechanism for the acid-catalyzed hydration of an alkene to give an alcohol and occurs by the following three steps. Step 1: Add a proton. Step 2: Make a new covalent bond between an electrophile (an electron-seeking species) and a nucleophile (an electron-donating species). Step 3: Take a proton away. Write an equation for each step and show by the use of curved arrows how each of these steps occurs. Show all bond-forming steps and bond-breaking steps.

Nicholas Sacco

Numerade Educator

Problem 76

Draw the structural formula for the hydrate formed by the reaction of acetone with water.

Colton Wang

Numerade Educator

Problem 77

With the exception of the acid-catalyzed conversion of ethylene to ethanol, primary alcohols cannot be prepared by the acid-catalyzed hydration of alkenes. The acid-catalyzed conversion of almost all other alkenes gives either secondary or tertiary alcohols. Explain why these two generalizations are valid.

Nicholas Sacco

Numerade Educator

Problem 78

Consider alkenes $A, B,$ and $C$, each of which has the same molecular formula, $\mathrm{C}_{6} \mathrm{H}_{12}$. Alkenes $\mathrm{B}$ and $\mathrm{C}$ can each be separated into cis and trans isomers. Upon catalytic reduction using $\mathrm{H}_{2}$ in the presence of a transition metal catalyst (Ni, Pd, or Pt), alkenes A, B, and $C$ all give hexane as the only product. Acidcatalyzed hydration of alkene C gives one alcohol with the molecular formula $\mathrm{C}_{6} \mathrm{H}_{14}$ O. Acid catalyzedhydration of alkene $\mathrm{B}$ gives an equal mixture of two alcohols, each with the molecular formula $\mathrm{C}_{6} \mathrm{H}_{14} \mathrm{O}$ Acid-catalyzed hydration of alkene C gives only a single alcohol with the molecular formula $\mathrm{C}_{6} \mathrm{H}_{14} \mathrm{O}$ Propose structural formulas for alkenes $A, B,$ and $C$ and the alcohols formed by acid-catalyzed hydration of each, consistent with these experimental results.

Nicholas Sacco

Numerade Educator

Problem 79

On acid-catalyzed hydration of alkenes A and C in the previous problem, each gives only one alcohol with the molecular formula $\mathrm{C}_{6} \mathrm{H}_{14}$ O. Draw the structural formulas for five other alkenes with the molecular formula $\mathrm{C}_{6} \mathrm{H}_{12}$, each of which will also give only one alcohol upon acid-catalyzed hydration.

Sana Riaz

Numerade Educator