Fundamentals of General, Organic, and Biological Chemistry

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

Chapter 14

Some Compounds with Oxygen, Sulfur, or a Halogen - all with Video Answers

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Chapter Questions

Problem 1

Identify each of the following compounds as an alcohol, a phenol, or an ether:

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Problem 2

Ethers have some slight solubility in water. Explain this using the concept of hydrogen bonding.

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Problem 3

Draw structures corresponding to the following names:
(a) 3-Methylhexan-1-ol
(b) 1 -Methyl-3-propylcyclopentanol
(c) 2,2 -Dimethylhexan-3-ol
(d) Heptan-3-ol
(e) 2,3 -Diethylcyclohexanol

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Problem 4

Give systematic names for the following compounds:

Ronald Prasad

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Problem 5

Identify each alcohol in Problems 14.3 and 14.4 as primary, secondary, or tertiary.

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Problem 6

Rank the following according to boiling point, highest to lowest:
(a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}$
(b) $\mathrm{CH}_{3} \mathrm{CH}_{2}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{OH}$
(c) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{3}$
(d) $\mathrm{CH}_{2}(\mathrm{OH}) \mathrm{CH}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{OH}$

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Problem 7

For each of the following molecules, (i) redraw using line structure format, (ii) identify its hydrophobic and hydrophilic parts, and (iii) predict its solubility in water.
(a) $\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{10} \mathrm{CH}_{2} \mathrm{OH}$
(b) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CHCH}_{3}$
(c) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CHCH}_{2} \mathrm{CH}_{2} \mathrm{OH}$

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Problem 8

What alkenes might be formed by dehydration of the following alcohols? If more than one product is possible in a given case, indicate which is major.

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Problem 9

What alcohols yield the following alkenes as the major product on dehydration?

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Problem 10

Two different alkenes will be formed by dehydration of the alcohol shown in the margin. Draw their structures using both condensed and line structure format, and label each as being either the major or minor product.

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Problem 11

What products would you expect from oxidation of the following alcohols?

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Problem 12

From what alcohols might the following carbonyl-containing products have been made?

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Problem 13

From what alcohols might the following carbonyl-containing products have been made $(\mathrm{red}=\mathrm{O},$ reddish-brown $=\mathrm{Br}) ?$

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Problem 14

Draw structures for the following:
(a) 2,4 -Dinitrophenol
(b) $m$ -Ethylphenol

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Problem 15

Name the following compounds:

Nicholas Sacco

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Problem 16

Name the following compounds:

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Problem 17

What disulfides would you obtain from oxidation of the following thiols?
(a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{SH}$
(b) 3-Methylbutane- 1 -thiol (skunk scent)

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Problem 18

Give systematic names for the following alkyl halides:

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Problem 19

2-Aminopropane is an achiral molecule, but 2 -aminobutane is chiral. Explain.

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Problem 20

Which of the following molecules are chiral? (Hint: Draw each molecule and analyze it as illustrated in Worked Example $14.2 .$.)
(a) 3-Chloropentane
(b) 2-Chloropentane
(c) $\mathrm{CH}_{3} \mathrm{CHCH}_{2} \mathrm{CHCH}_{2} \mathrm{CH}_{3}$

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Problem 21

Give IUPAC names for the following compounds (black $=\mathrm{C}, \mathrm{red}=\mathrm{O},$ white $=\mathrm{H})$

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Problem 22

Predict the product of the following reaction:

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Problem 23

Predict the products of the following reaction:

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Problem 24

The compound pictured here is a thiol.
(a) Draw its line structure, and
(b) draw the structure of the disulfide formed when it is treated with an oxidizing agent ( yellow $=\mathrm{S}$ ).

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Problem 25

From what alcohols might the following carbonyl compounds have been made ( reddish-browm = Br)?

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Problem 26

How do alcohols, ethers, and phenols differ structurally?

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Problem 27

What is the structural difference between primary, secondary, and tertiary alcohols?

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Problem 28

Why do alcohols have higher boiling points than ethers of the same molecular mass?

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Problem 29

Which is the stronger acid, ethanol or phenol?

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Problem 30

The Taxane nucleus is shown here; it is the basis of a number of new drugs used to treat cancers. Identify the functional groups present in this molecule.

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Problem 31

Vitamin $\mathrm{E}$ has the structure shown. Identify the functional group to which each oxygen belongs.

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Problem 32

Give systematic names for the following alcohols:

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Problem 33

Give systematic names for the following compounds:

Ronald Prasad

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Problem 34

Draw structures corresponding to the following names:
(a) 2,4 -Dimethylheptan- 2 -ol
(b) 2,2 -Diethylcyclohexanol
(c) 5 -Ethyl-5-methylheptan-1-ol
(d) 4-Ethylhexan-2-ol
(e) 3-Methoxycyclooctanol
(f) 3,3 -Dimethylheptane-1,6-diol

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Problem 35

Draw structures corresponding to the following names:
(a) Isopropyl methyl ether
(b) $o$ -Dihydroxybenzene (catechol)
(c) Phenyl tert-butyl ether
(d) $m$ -Iodophenol
(e) 2,4 -Dimethoxy-3-methylpentane
(f) 3-Methoxy-4-methylpent-1-ene

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Problem 36

(a) Identify each alcohol named in Problem 14.32 as primary, secondary, or tertiary.
(b) Classify each alcohol in Problem 14.32 as watersoluble or water insoluble. Identify the hydrophobic and hydrophilic areas of each alcohol.

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Problem 37

Locate the alcohol functional groups in the taxane nucleus (Problem 14.30), and identify each as primary, secondary, or tertiary.

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Problem 38

Arrange the following 6-carbon compounds in order of their expected boiling points, and explain your ranking:
(a) Hexane
(b) Hexan-1-ol
(c) Dipropyl ether $\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\right)$

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Problem 39

Glucose is much more soluble in water than hexan-1-ol, even though both contain 6 carbons. Explain.

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Problem 40

What functional group is formed on oxidation of a secondary alcohol? Demonstrate your answer using isopropanol.

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Problem 41

What structural feature is necessary for an alcohol to undergo oxidation reactions?

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Problem 42

What product can form on oxidation of a primary alcohol with an excess of oxidizing agent?

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Problem 43

What type of product is formed on reaction of an alcohol with Na metal?

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Problem 44

Assume that you have samples of the following two compounds, both with formula $\mathrm{C}_{7} \mathrm{H}_{8} \mathrm{O} .$ Both compounds dissolve in ether, but only one of the two dissolves in aqueous $\mathrm{NaOH}$. How could you use this information to distinguish between them?

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Problem 45

Which of the following alcohols can undergo oxidation? Draw the line structure of the product expected for those that can. Assume an excess of oxidizing agent is present.

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Problem 46

The following alkenes can be prepared by dehydration of an appropriate alcohol. Show the structure of the alcohol in each case that would provide the alkene shown as the major product.

Grigoriy Sereda

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Problem 47

What alkenes might be formed by dehydration of the following alcohols? If more than one product is possible, indicate which you expect to be major.

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Problem 48

What carbonyl-containing products would you obtain from the oxidation of the following alcohols? If no reaction occurs, write "NR."

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Problem 49

What alcohols would you oxidize to obtain the following carbonyl compounds?

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Problem 50

What is the most noticeable characteristic of thiols?

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Problem 51

What is the structural relationship between a thiol and an alcohol?

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Problem 52

The amino acid cysteine forms a disulfide when oxidized. What is the structure of the disulfide?

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Problem 53

Oxidation of a dithiol such as hexane-2,5-dithiol forms a six-membered ring containing a disulfide group as part of the ring. Draw the structure of this cyclic disulfide (Hint:
Draw the starting compound in line structure format first).

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Problem 54

The boiling point of propanol is $97^{\circ} \mathrm{C}(370 \mathrm{~K})$, much higher than that of either ethanethiol $\left(37^{\circ} \mathrm{C} / 310 \mathrm{~K}\right)$ or chloroethane $\left(13^{\circ} \mathrm{C} / 286 \mathrm{~K}\right)$, even though all three compounds have similar molecular masses. Explain.

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Problem 55

Propanol is very soluble in water, but ethanethiol and chloroethane are only slightly soluble. Explain.

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Problem 56

Define the following terms:
(a) Chiral
(b) Achiral
(c) Chiral carbon
(d) Enantiomer

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Problem 57

Are the following items chiral or achiral? Give a justification for your answers.
(a) A fork
(b) This textbook
(c) Your right hand
(d) A blank $3 \times 5$ index card

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Problem 58

Identify the chiral center(s) in each of the following molecules:
(a) 2 -Methylpentan- 3 -ol
(b) 3-Chlorobutan-1-ol
(c)
(d)

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Problem 59

Are the following molecules chiral or achiral? If they are chiral, identify the chiral carbon atom(s).
(a) Pentan-3-ol
(b) 2-Bromobutane
(c) 2 -Methylcyclohexanol

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Problem 60

Name all unbranched ether and alcohol isomers with formula $\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O},$ and write their structural formulas.

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Problem 61

Thyroxine (Section 14.9) is synthesized in the body by reaction of thyronine with iodine. Write the reaction, and tell what kind of process is occurring (Hint: See Section 13.5).

David Collins

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Problem 62

Propan 1-ol is freely soluble in water, butan 1 -ol is margin ally soluble, and hexan-1-ol is essentially insoluble. Explain.

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Problem 63

Phenols undergo the same kind of substitution reactions that other aromatic compounds do (Section 13.11 ). Formulate the reaction of $p$ -methylphenol with $\mathrm{Br}_{2}$ to give a mixture of two substitution products.

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Problem 64

What is the difference between an antiseptic and a disinfectant?

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Problem 65

Which of the alcohols pictured in Problem 14.47 are achiral?

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Problem 66

Which of the alcohols pictured in Problem 14.48 are chiral? Indicate the chiral carbons for those that are chiral.

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Problem 67

Write the formulas and IUPAC names for the following common alcohols (Hint: See Table 14.1).
(a) Rubbing alcohol
(b) Wood alcohol
(c) Grain alcohol
(d) Diol used as antifreeze (two answers)

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Problem 68

Name the following compounds:

Nicholas Sacco

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Problem 69

Complete the following reactions:

Ronald Prasad

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Problem 70

The aroma of roses is due to geraniol.
(a) What is the systematic name of geraniol?
(b) When geraniol is oxidized, the aldehyde citral, one of the compounds responsible for lemon scent, is formed. Write the structure of citral.

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Problem 71

"Designer vinegars" have become very popular over the past decade. Vinegars made from champagne, merlot, and other wines are but a few of these. All wines contain ethanol, and these vinegars are simply wines containing microorganisms that have caused oxidation of the ethanol present. If vinegar is simply ethanol that has been oxidized, what is the structure of the acid formed?

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Problem 72

"Flaming" desserts, such as cherries jubilee, use the ethanol in brandy or other distilled spirits as the flame carrier. Write the equation for the combustion of ethanol.

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Problem 73

(a) Draw all possible cyclic $\mathrm{C}_{7} \mathrm{H}_{14} \mathrm{O}$ alcohol isomers having a cyclohexane ring and a methyl group. (Hint:
Adapt the method described in Worked Example 12.12 to arrive at your answers.)
(b) Identify all chiral centers in the isomers that you drew for part (a).

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Problem 74

Using the alcohol shown, draw all the possible alkenes that might be formed on its dehydration. Which do you think will be the major product(s)? Which do you think will be the minor product(s)? It is alright to have more than one major and minor product.

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Problem 75

Using the alcohol shown, draw all the possible alkenes that might be formed on its dehydration. Which alkenes can exist as cis-trans isomers? Draw them, in both condensed and line structure, and identify each as cis or trans. Explain your choices.

Zubair Abdulla

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