Organic Chemistry, 8e (Wade)

Chapter 25 Lipids
1) Which of the following lipids is an example of a simple lipid?
A) fat
B) terpene
C) oil
D) wax
E) none of the above
Answer: B
Diff: 1
Section: 25.1
2) ________ lipids are those that can be easily hydrolyzed to simpler constituents.
Answer: Complex
Diff: 1
Section: 25.1
3) Is cholesterol an example of a simple lipid or a complex lipid? Explain briefly.
Answer: Chloesterol is a simple lipid; it cannot be easily hydrolyzed by aqueous acid or base.
Diff: 1
Section: 25.1
4) Define lipid.
Answer: Lipids are substances that can be extracted from cells and tissues by nonpolar organic solvents.
Diff: 1
Section: 25.1
5) Which of the following is a complex lipid?
A) testosterone
B) tristearin
C) arachidic acid
D) sodium palmitate
E) b-carotene
Answer: B
Diff: 2
Section: 25.1
6) Name two of the three predominant groups of simple lipids.
Answer: steroids, prostaglandins, terpenes
Diff: 2
Section: 25.1

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7) Are triglycerides simple lipids? Explain.

Answer: No, triglycerides are complex lipids. These esters are readily hydrolyzed by aqueous base to
give glycerol and the appropriate fatty acid carboxylates.
Diff: 2
Section: 25.1
8) What group of lipids are esters of long-chain fatty acids and long-chain alcohols?
Answer: waxes
Diff: 1
Section: 25.2
9) Which of the following terms best describes the compound below?
CH3(CH2)26CO2CH2(CH2)32CH3
A) a fat
B) an oil
C) a terpene
D) an unsaturated triglyceride
E) a wax
Answer: E
Diff: 2
Section: 25.2
10) Which of the following peaks would one expect to observe as a major, strong peak in the IR
spectrum of a lipid wax?
A) 3200-3500 cm-1
B) 2710 cm-1
C) 2200 cm-1
D) 1730 cm-1
E) 1620 cm-1
Answer: D
Diff: 2
Section: 25.2
11) Which best describes the lipid shown below?

A) wax
B) triglyceride
C) saturated fatty acid
D) unsaturated fatty acid
E) lecithin
Answer: A
Diff: 2
Section: 25.2
12) What IR stretch would most readily distinguish carnauba wax from paraffin wax?
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Answer: Carnauba wax is a true wax, an ester of a fatty acid and a long chain alcohol, while paraffin
wax is a mixture of high molecular weight hydrocarbons. The carbonyl stretch of the ester functionality
in carnauba would readily distinguish it.
Diff: 2
Section: 25.2
13) When spermaceti is heated in aqueous potassium hydroxide, CH3(CH2)14CH2OH and
CH3(CH2)14CO2-K+ are formed. Provide the structure of spermaceti.
Answer: CH3(CH2)14CO2CH2(CH2)14CH3
Diff: 2
Section: 25.2
14) Which of the following terms best describes the compound below?

A) a wax
B) a saturated triglyceride
C) a terpene
D) a prostaglandin
E) a lecithin
Answer: B
Diff: 1
Section: 25.3
15) Which of the following terms best describes the compound below?
CH3(CH2)12CO2H
A) a triglyceride
B) a fatty acid
C) a wax
D) a prostaglandin
E) a phosphatidic acid
Answer: B
Diff: 1
Section: 25.3

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16) Which of the following terms best describes the compound below?
CH3(CH2)7CHCH(CH2)7CO2H
A) an unsaturated fatty acid
B) a triglyceride
C) a synthetic detergent
D) a micelle
E) isoprene
Answer: A
Diff: 1
Section: 25.3
17) Which of the following correctly describe(s) glyceryl trimyristate?
A) an ester
B) a complex lipid
C) a triglyceride
D) a fat
E) all of the above
Answer: E
Diff: 1
Section: 25.3
18) How many molecules of fatty acid are needed to produce one molecule of a fat or oil?
A) 1
B) 1.5
C) 2
D) 3
E) 6
Answer: D
Diff: 1
Section: 25.3
19) Oleic acid is an example of ________ fatty acid. A molecule of oleic acid contains a single carboncarbon double bond and ________ carbon atoms.
A) an unsaturated; 18
B) an unsaturated; 9
C) a saturated; 52
D) a saturated; 18
E) a saturated; 9
Answer: A
Diff: 1
Section: 25.3

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20) In the formation of a triacylglyceride, what two functional groups chemically combine?
A) carboxylic acid and an amine
B) carboxylic acid and an alcohol
C) alcohol and an aldehyde
D) alcohol and a ketone
E) two different alcohols
Answer: B
Diff: 1
Section: 25.3
21) Which reagent below could best be used to distinguish CH3(CH2)10CO2H from
CH2(CH2)4CH=CH(CH2)4CO2H?
A) NaOH, H2O
B) Ag(NH3)2+
C) H2Cr2O7
D) Br2/CCl4
E) NH3
Answer: D
Diff: 1
Section: 25.3
22) Why are fats more efficient sources of long-term energy than carbohydrates?
Answer: Metabolism of a gram of fat releases over twice as much energy as a gram of carbohydrate.
Diff: 1
Section: 25.3
23) What does the term polyunsaturated mean when used to describe a triglyceride?
Answer: This term indicates the presence of several carbon-carbon double bonds in the fatty acid
residues of the triglyceride.
Diff: 1
Section: 25.3
24) What reagent is needed to convert CH3(CH2)14CO2H to CH3(CH2)14CH2OH?
Answer: LiAlH4
Diff: 1
Section: 25.3
25) What reagent is needed to convert CH3(CH2)14CH2OH to CH3(CH2)14CHO?
Answer: PCC (pyridinium chlorochromate)
Diff: 1
Section: 25.3

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26) What reagent is needed to convert CH3(CH2)14CO2H to CH3(CH2)14COCl?

Answer: SOCl2
Diff: 1
Section: 25.3
27) Which of the following is an unsaturated fatty acid?
A) adipic acid
B) linoleic acid
C) stearic acid
D) palmitic acid
E) oxalic acid
Answer: B
Diff: 2
Section: 25.3
28) Two families of fatty acids called the - 6 and -3 fatty acids are of significant interest in the area
of nutrition. Which of the following structures would be classified as an -3 fatty acid?
A)

B)

C)

D)

E)

Answer: A
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Diff: 2
Section: 25.3
29) Which best describes the lipid shown below?

A) wax
B) triglyceride
C) saturated fatty acid
D) unsaturated fatty acid
E) lecithin
Answer: B
Diff: 2
Section: 25.3
30) Which best describes the lipid shown below?

A) wax
B) triglyceride
C) saturated fatty acid
D) unsaturated fatty acid
E) lecithin
Answer: C
Diff: 2
Section: 25.3
31) Which best describes the lipid shown below?

A) wax
B) triglyceride
C) saturated fatty acid
D) unsaturated fatty acid
E) lecithin
Answer: D
Diff: 2
Section: 25.3
32) Name the compound whose formula is CH3(CH2)12CO2H.
Answer: myristic acid
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Diff: 2
Section: 25.3
33) Lauric acid has the formula CH3(CH2)10CO2H. Provide the structure of the triglyceride which was
formed from three equivalents of lauric acid.
Answer:

Diff: 2
Section: 25.3
34) Which of the following statements correctly describe(s) the relationship between the structure of a
fatty acid and its melting point?
A) Saturated fatty acids have melting points that increase gradually with their molecular weights.
B) The presence of a trans double bond in the fatty acid has a greater effect on its melting point than
does the presence of a cis double bond.
C) As the number of double bonds in a fatty acid increases, its melting point decreases.
D) both A and C
E) A, B, and C
Answer: D
Diff: 2
Section: 25.3
35) Which of the following fatty acids has the highest melting point?
A) lauric acid
B) myristic acid
C) palmitic acid
D) stearic acid
E) linoleic acid
Answer: D
Diff: 2
Section: 25.3

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36) Which of the following fatty acids has the lowest melting point?
A) lauric acid
B) myristic acid
C) palmitic acid
D) stearic acid
E) linoleic acid
Answer: E
Diff: 2
Section: 25.3
37) Which of the following oils is the least polyunsaturated?
A) herring oil
B) corn oil
C) olive oil
D) soybean oil
E) canola oil
Answer: A
Diff: 2
Section: 25.3
38) Which of the following oils has the highest composition of one single fatty acid?
A) herring oil
B) olive oil
C) soybean oil
D) canola oil
Answer: B
Diff: 2
Section: 25.3
39) Which of the following oils has the highest percentage of saturated fatty acid?
A) herring oil
B) olive oil
C) soybean oil
D) canola oil
Answer: A
Diff: 2
Section: 25.3
40) Which of the following oils would consume the greatest number of equivalents of hydrogen when
subject to catalytic hydrogenation?
A) corn oil
B) olive oil
C) canola oil
D) linseed oil
Answer: D
Diff: 2
Section: 25.3
41) When linoleic acid is hydrogenated, what organic compound is produced and how does its melting
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point compare to that of linoleic acid?

Answer: Stearic acid is produced, and its melting point is higher than that of linoleic acid.
Diff: 2
Section: 25.3
42) Why do most fatty acids contain an even number of carbons?
Answer: Most fatty acids contain an even number of carbons because they are biosynthesized from twocarbon acetic acid units.
Diff: 2
Section: 25.3
43) Which packs more readily into a crystal lattice, tristearin or triolein? Explain.
Answer: Tristearin packs more readily into a crystal lattice, because the elements of unsaturation in
triolein disrupt packing.
Diff: 2
Section: 25.3
44) Was the compound shown below more likely isolated from an animal or a plant? Explain.

Answer: The compound shown is a polyunsaturated triglyceride. Such triglycerides are liquid at room
temperature (i.e., are oils) and are more likely to have been isolated from a plant.
Diff: 2
Section: 25.3
45) How is a fat distinguished from an oil, (a) based on a physical property difference and (b) based on a
difference in molecular structure?
Answer: Fats have higher melting points than oils and tend to have fewer carbon-carbon double bonds
(sites of unsaturation) present.
Diff: 2
Section: 25.3
46) Why and in what fashion does the presence of a double bond in a fatty acid affect its melting point
relative to the system where the double bond is absent?
Answer: The presence of a double bond lowers the melting point. The double bond introduces a "kink"
in the carbon chain which retards efficient molecular packing and thus hinders solidification.
Diff: 2
Section: 25.3

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47) When a vegetable oil is partially hydrogenated, how is its structure altered and how is its melting
point affected?
Answer: H2 is added across some of the carbon-carbon double bonds present. This decreases the
number of sites of unsaturation and consequently increases the degree of saturation. The melting point
increases.
Diff: 2
Section: 25.3
48) Draw the structure of the product which results when the compound shown below is completely
hydrogenated using excess H2.

Answer:

Diff: 2
Section: 25.3
49) Which of the following are omega-3 fatty acids?
A) myristic acid
B) oleic acid
C) linolenic acid
D) arachidonic acid
Answer: C
Diff: 2
Section: 25.3

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50) With which of the following reagents would linoleic acid not react?
A) HBr
B) Br2
C) O3
D) warm, concentrated KMnO4
E) Na2Cr2O7
Answer: E
Diff: 2
Section: 25.3
51) What reagents would you use to prepare octadecanal from stearic acid, CH3(CH2)16CO2H?
Answer:
1. LiAlH4
2. PCC
or
1. SOCl2
2. LiAlH[O(CH3)3]3
Diff: 2
Section: 25.3
52) How can the degree of unsaturation of an oil be gauged using a solution of bromine in carbon
tetrachloride?
Answer: The bromine solution is dark red in color. Upon reaction with C=C units, bromine is
consumed and the red color disappears. The more bromine solution that must be added to produce a
persistent red color, the more unsaturated the oil.
Diff: 2
Section: 25.3
53) Provide the major organic product of the reaction shown below.

Answer:
Diff: 2
Section: 25.3
54) How would you prepare CH3(CH2)14CH2Br from palmitic acid, CH3(CH2)14CO2H?
Answer:
1. LiAlH4
2. PBr3 or HBr
Diff: 2
Section: 25.3

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55) How would you prepare CH3(CH2)14CH2NH2 from palmitic acid, CH3(CH2)14CO2H?
Answer:
1. SOCl2
2. NH3
3. LiAlH4
Diff: 2
Section: 25.3
56) What are the two major organic products which result when oleic acid,
CH3(CH2)7CH= CH(CH2)7CO2H, is treated with ozone followed by dimethyl sulfide?
Answer: CH3(CH2)7CHO + OHC(CH2)7CO2H
Diff: 2
Section: 25.3
57) Using solely a fatty acid as your starting material, how would you synthesize a wax?
Answer: Reduce the fatty acid to the alcohol with lithium aluminum hydride and react it with the acid
chloride produced by treating the acid with thionyl chloride.
Diff: 2
Section: 25.3
58) Provide the structure of the major organic compound that results when palmitic acid,
CH3(CH2)14CO2H, is heated in methanol containing catalytic acid.
Answer: CH3(CH2)14CO2CH3,
Diff: 2
Section: 25.3
59) Provide the structure of the major organic compound that results when palmitic acid,
CH3(CH2)14CO2H, is heated in ethanol containing catalytic acid.
Answer: CH3(CH2)14CO2CH2CH3,
Diff: 2
Section: 25.3
60) Provide the major organic product of the following reaction.

Answer:
Diff: 2
Section: 25.3

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61) Provide the major organic product of the following reaction.

Answer: CH3(CH2)14CH(OH)CH3
Diff: 2
Section: 25.3
62) Provide the major organic product of the following reaction sequence.

Answer: CH3(CH2)14CO2CH2(CH2)14CH3
Diff: 2
Section: 25.3
63) Provide the major organic product of the following reaction sequence.

Answer: CH3(CH2)14CONHCH2CH3
Diff: 2
Section: 25.3
64) Given a single triglyceride which contains three identical and fully saturated fatty acid residues,
which of the following terms accurately describe(s) it?
A) chiral
B) optically active
C) meso
D) optically inactive
E) both A and B
Answer: D
Diff: 3
Section: 25.3
65) Arrange the following fatty acids in order of increasing melting point:
stearic acid, linolenic, linoleic, and oleic.
Answer: linolenic < linoleic < oleic < stearic
Diff: 3
Section: 25.3

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66) Would the addition of HCl to the double bond of oleic acid, CH3(CH2)7CH= CH(CH2)7CO2H,
occur with high regioselectivity? Explain.
Answer: No. The two possible carbocation intermediates are very similar in structure and stability and
would thus be formed at comparable rates.
Diff: 3
Section: 25.3
67) ________ is the base-promoted hydrolysis of fats and oils.
Answer: Saponification
Diff: 1
Section: 25.4
68) Draw the two fatty acid structures that result from acid and base hydrolysis of a triacylglyceride and
explain how they differ. (Use a core structure of 10 carbon atoms)
Answer:

Acid hydrolysis will result in the production of an insoluble protonated form of the fatty acid whereas
base hydrolysis will result in the production of a deprotonated more water soluble form of the fatty acid
Diff: 1
Section: 25.4
69) Which of the following terms best describes the interior of a soap micelle in water?
A) hydrophobic
B) hydrophilic
C) hard
D) saponified
E) hydrogenated
Answer: A
Diff: 1
Section: 25.4

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70) Which of the following terms best describes the exterior surface of a soap micelle in water?
A) hydrophobic
B) hydrophilic
C) hard
D) saponified
E) hydrogenated
Answer: B
Diff: 1
Section: 25.4
71) The sodium or potassium salt of a fatty acid is known as a ________.
Answer: soap
Diff: 1
Section: 25.4
72) What do we call a mixture of two immiscible liquids in which one liquid is dispersed throughout the
other in small droplets?
Answer: emulsion
Diff: 1
Section: 25.4
73) Describe the intermolecular interaction of the surface carboxylate groups of a micelle and the
surrounding water.
Answer: hydrogen bonding
Diff: 1
Section: 25.4
74) Which of the following terms best describes the compound below?
CH3(CH2)4CHCHCH2CHCH(CH2)7CO2-Na+
A) a wax
B) a soap
C) a terpene
D) a lecithin
E) a prostaglandin
Answer: B
Diff: 2
Section: 25.4

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75) Which of the following chemical reactions could be used to distinguish between a polyunsaturated
vegetable oil and a petroleum oil containing a mixture of saturated and unsaturated hydrocarbons?
A) addition of bromine in carbon tetrachloride
B) ozonolysis
C) hydrogenation
D) lipidification
E) saponification
Answer: E
Diff: 2
Section: 25.4
76) Provide the structures of the major organic products which result when tristearin (shown below) is
heated in aqueous solution of sodium hydroxide.

Answer: HOCH2CHOHCH2OH and CH3(CH2)16CO2-Na+

Diff: 2
Section: 25.4
77) What organic compounds result when tristearin is heated in aqueous sodium hydroxide?
Answer: glycerol and sodium stearate
Diff: 2
Section: 25.4
78) Which of the following terms best describes the compound below?

A) a phospholipid
B) a cationic detergent
C) an alkaloid
D) a hard-water scum
E) a component of most lipid bilayers
Answer: B
Diff: 2
Section: 25.4

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79) Which formula best characterizes hard-water scum?

A) [CH3(CH2)16CO2]2Ca
B) CH3CH2CH=CHCH2CH2CH2CO2H
C) CH3(CH2)16CO2Na
D) CH3(CH2)16CO2H
E) CH3(CH2)16SO3Na
Answer: A
Diff: 2
Section: 25.4
80) Which of the following is an advantage of using an alkylbenzenesulfonate detergent over a common
soap?
A) The alkylbenzenesulfonate detergent is uncharged.
B) The alkylbenzenesulfonate detergent has no hydrophobic region.
C) Greases are not emulsified by soaps.
D) Calcium, magnesium, and iron salts of sulfonic acids are soluble in water.
E) Sulfonates are protonated at higher pH's than are carboxylates.
Answer: D
Diff: 2
Section: 25.4
81) Provide the structure of a soap. Label the hydrophilic and hydrophobic regions of the molecule you
have drawn.
Answer:

Diff: 2
Section: 25.4
82) What occurs when an aqueous solution of sodium stearate is treated with a solution of calcium ions?
Answer: Calcium stearate, an insoluble salt, precipitates.
Diff: 2
Section: 25.4
83) What is a micelle?
Answer: A micelle is a spherical cluster of soap molecules with their polar carboxylate groups on the
surface of the cluster and their hydrophobic hydrocarbon tails enclosed within.
Diff: 2
Section: 25.4

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84) Describe how soaps function as cleaning agents.

Answer: Soaps aggregate in water to form clusters called micelles. The polar carboxylate groups of the
soaps form the surface of the micelle and hydrogen bond to the surrounding water. The interior of the
micelles is composed of the nonpolar, hydrophobic portions of the soap molecules. Grease and dirt are
essentially nonpolar and hence have limited solubility in water. In soapy water however, grease and dirt
will dissolve in the nonpolar interior of the soap micelles which are in turn soluble in the water.
Diff: 2
Section: 25.4
85) What is an emulsion?
Answer: A mixture of two insoluble phases wherein one phase is dispersed throughout the other in
small droplets is an emulsion.
Diff: 2
Section: 25.4
86) Why do soaps work poorly in acidic water?
Answer: Soap molecules are protonated in acidic water to the free fatty acid, which is insoluble in water
and thus forms a greasy "acid scum" precipitate.
Diff: 2
Section: 25.4
87) Why do soaps work poorly in hard water?
Answer: Hard water contains reasonably large amounts of calcium, magnesium, and iron ions. These
ions exchange with the sodium or potassium ions of the soap to form insoluble salts called hard water
scum.
Diff: 2
Section: 25.4
88) Describe the general molecular features which a nonionic detergent would possess.
Answer: A nonionic detergent would possess a hydrophilic region rich in uncharged yet polar
functionality (like hydroxyl groups) and a hydrophobic region which is essentially hydrocarbon in
nature.
Diff: 2
Section: 25.4

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89) Which of the following species would be expected to be insoluble in water?

(More than one answer is possible.)
A)
B)
C)

D)

Answer: A, C
Diff: 2
Section: 25.4
90) How many molecules of fatty acid are needed to make one molecule of a cephalin?
A) 0
B) 1
C) 1.5
D) 2
E) 3
Answer: D
Diff: 1
Section: 25.5
91) Explain which structural features of phospholipids make them suitable components from which to
form a lipid bilayer.
Answer: Phospholipids have a hydrophilic region which contains an ionized phosphatidic acid or ester
group and a hydrophobic portion which contains two fatty acid esters.
Diff: 2
Section: 25.5
92) Provide a sketch of a lipid bilayer. Label the hydrophobic and hydrophilic regions.
Answer:

Diff: 2
Section: 25.5
93) Which of the following terms correctly describe(s) the compound below?
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A) a phospholipid
B) a phosphoglyceride
C) a cephalin
D) a molecule which contains a polar head group
E) all of the above
Answer: E
Diff: 2
Section: 25.5
94) Which of the following is another name for a phosphatidyl choline?
A) a steroid
B) a lecithin
C) an androsterone
D) a cephalin
E) a triglyceride
Answer: B
Diff: 2
Section: 25.5
95) How many hydrocarbon tails are typically present in a phospholipid molecule?
A) 0
B) 1
C) 2
D) 3
E) 4
Answer: C
Diff: 2
Section: 25.5

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96) Lecithins are phospholipids wherein the alcohol choline is esterified to a phosphatidic acid. Provide
the structure of choline.
Answer:

Diff: 2
Section: 25.5
97) Phospholipids are generally produced from the phosphatidate core structure with a polar head
modifying group such as choline. However, a phospholipid called sphingomyelin (see below) is found
abundantly in brain and fast neurons. Circle and label all structural features of sphingomyelin which are
different from lecithin.

Answer:

Diff: 2
Section: 25.5

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98) Modify the phosphatidic acid below so that it becomes a lecithin.

Answer:

Diff: 2
Section: 25.5

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99) Which of the following is a lecithin?

A)

B)

C)

D)

Answer: C
Diff: 2
Section: 25.5
100) What class of lipids functions to control blood pressure, inflammatory responses, and the clotting
of blood?
A) prostaglandins
B) steroid
C) phospholipids
D) triglyceride
Answer: A
Diff: 2
Section: 25.5

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101) Show the linkage through which choline [HOCH2CH2N(CH3)3+] is linked to a phosphatidic acid
to form a lecithin.
Answer:

Diff: 3
Section: 25.5
102) Which of the following terms best describes the compound below?

A) a sesquiterpene
B) a steroid
C) a protein
D) a cephalin
E) an essential oil
Answer: B
Diff: 1
Section: 25.6
103) Most of the principal sex hormones in humans are:
A) triglycerides.
B) prostaglandins.
C) steroids.
D) phospholipids.
E) terpenes.
Answer: C
Diff: 1
Section: 25.6

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104) Which of the following terms best describes the compound below?

A) a trans A-B steroid

B) a cis A-B steroid
C) a complex lipid
D) a sesquiterpene
E) a synthetic detergent
Answer: A
Diff: 2
Section: 25.6
105) The compound ________ is used in the treatment of asthma and rheumatoid arthritis.
A) digitoxigenin
B) cortisol
C) PGE1
D) ethynyl estradiol
E) myrcene
Answer: B
Diff: 2
Section: 25.6

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106) Which of the following natural products can be correctly classified as a steroid?
A)

B)

C)

D)

Answer: B
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Diff: 2
Section: 25.6
107) ________ is a common biological intermediate and is the biosynthetic precursor to other steroids.
Answer: Cholesterol
Diff: 2
Section: 25.6
108) Draw the basic 4-ring skeletal structure found in steroids.
Answer:

Diff: 2
Section: 25.6
109) The following paraminabeolide was isolated from a Formosan soft coral and has been found to
have anti-inflammatory action (J. Nat. Prod. 2011, 1132). What is the lipid classification of
paraminabeolide?

A) terpene
B) triglyceride
C) steroid
D) prostaglandin
Answer: C
Diff: 2
Section: 25.6

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110) Draw a neat conformational structure of the compound below

Answer:

Diff: 3
Section: 25.6
111) Circle all of the structural features of sodium glycocholate (bile salt) which are different from
cholesterol, its parent compound, and explain why it behaves like a detergent.

Answer:

The structure can act as a detergent because it has both hydophobic and hydrophilic characteristics. The
addition of the ionized carboxylate acts as the polar head of the molecule and the sterol ring structure
acts as the nonpolar tail
Diff: 3
Section: 25.6
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112) Which of the following terms best describes the compound below?

A) a lecithin
B) a diterpene
C) a steroid
D) a glyceride
E) a prostaglandin
Answer: E
Diff: 2
Section: 25.7
113) Prostaglandins are derived from ________.
A) serine
B) hemoglobin
C) -pinene
D) stearic acid
E) arachadonic acid
Answer: E
Diff: 2
Section: 25.7
114) Which of the following structural features is not typically found in a prostaglandin?
A) a carboxyl group
B) a 5-membered ring
C) a hydroxyl group
D) a carbon-carbon double bond
E) an amino group
Answer: E
Diff: 2
Section: 25.7

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115) Geranial is shown below. How many isoprene units can be found in this compound?

A) 1
B) 2
C) 3
D) 4
E) 5
Answer: B
Diff: 1
Section: 25.8
116) Terpenes which contain two isoprene units are called ________.
A) monoterpenes
B) sesquiterpenes
C) diterpenes
D) triterpenes
E) tetraterpenes
Answer: A
Diff: 1
Section: 25.8
117) The C:H ratio present in most terpenes is ________.
A) 1:2
B) 3:8
C) 2:6
D) 5:8
E) 4:5
Answer: D
Diff: 1
Section: 25.8
118) Which of the following terms best describes terpenes?
A) nonpolar
B) ionic
C) protein
D) carbohydrate
E) nucleic acid
Answer: A
Diff: 1
Section: 25.8

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119) Which of the following terms best describes the compound below?

A) a diterpene
B) an unsaturated triglyceride
C) a monoterpene
D) a complex lipid
E) a steroid
Answer: C
Diff: 2
Section: 25.8
120) -carotene is a naturally occurring compound containing 40 carbon atoms which has a significant
extended system of conjugated double bonds. This compound is also a terpene. How many isoprene
units are present in -carotene?
A) 2
B) 4
C) 6
D) 8
E) 10
Answer: D
Diff: 2
Section: 25.8
121) Camphor is an example of a ________.
A) terpene
B) triglyceride
C) prostaglandin
D) steroid
E) phospholipid
Answer: A
Diff: 2
Section: 25.8

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122) The following natural product has been examined for cytotoxic activity. How should this natural
product be classified?

A) monoterpene
B) sesquiterpene
C) diterpene
D) triterpene
Answer: B
Diff: 2
Section: 25.8
123) Provide the structure of isoprene.
Answer:
Diff: 2
Section: 25.8
124) Circle the isoprene units present in menthol below.

Answer:

Diff: 2
Section: 25.8

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125) A terpene is believed to have one of the structures below. Based on the isoprene rule, which
structure is more likely. Explain your reasoning.

or
Answer:

Diff: 3
Section: 25.8
126) Two equivalents of isoprene are produced when limonene (shown below) is virorously heated.
What single-step process has occurred?

Answer: a reverse or retro Diels Alder reaction.

Diff: 3
Section: 25.8
127) The following compound was isolated from the liverwort Porella chilensis and has shown to be
effective in inhibiting the human pathogen Pseudomonas aeruginosa. Show that this structure belongs to
the terpene family by dividing the molecule up into each isoprene unit and then give the terpene
classification.

Answer:

Diff: 3
Section: 25.8

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