Deck 19: Organic Chemistry Fuels, Pharmaceuticals, and Modern Materials

Question 1

Organic chemistry encompasses the chemistry of all

A)hydrocarbons.
B)functional groups.
C)monomers, oligomers, and polymers.
D)naturally occurring compounds.
E)carbon-containing compounds.

Answer 1

carbon-containing compounds.

Question 2

Without working out all the structures, which has the larger number of structural isomers, C₁₄H₃₀ or C₁₅H₃₂?

A)C₁₄H₃₀
B)C₁₅H₃₂
C)They have the same number of isomers.
D)There is no way to tell without working out all the structures.
E)It depends on the number of multiple bonds in the molecule.

Answer 2

C₁₅H₃₂

Question 3

A hydrocarbon is a compound that contains

A)carbon with hydrogen and oxygen in the ratio 2:1.
B)carbon with hydrogen and oxygen in any ratio.
C)only carbon and hydrogen.
D)carbon, hydrogen, and any functional groups.
E)only carbon, hydrogen, and oxygen.

Answer 3

only carbon and hydrogen.

Question 4

Which of the following statements regarding hydrocarbons is NOT correct?

A)Alkanes contain carbons that are sp3 hybridized.
B)Alkynes contain at least one carbon-carbon double bond.
C)The carbons in the functional group characterizing an alkene are sp2 hybridized.
D)The general chemical formula for alkanes is C_nH_2n+2.
E)The general formula for cycloalkanes is C_nH_2n.

Question 5

The C - C - C bond angles in octane CH₃CH₂CH₂CH₂CH₂CH₂CH₂CH₃) are all

A)180 $\degree$ .
B)120 $\degree$ .
C)90 $\degree$ .
D)109.5 $\degree$ .
E)60 $\degree$ .

Question 6

The basic building block of a polymer is called

A)a functional group.
B)a monomer.
C)a monotone.
D)an oligomer.
E)an addition.

Question 7

What is NOT a correct formula for the compound illustrated below?

A)CH₃CH₂)₅CH₃
B)CH₃)₂CHCH₂CHCH₃)₂
C)CH₃CHCH₃)CH₂CHCH₃)CH₃
D)C₇H₁₆
E)

Question 8

Which of the following are true regarding cyclohexane, whose carbon skeleton is shown?
I.The molecule is flat.
II.Each carbon is bonded to four other atoms.
III.Each carbon is sp3 hybridized.

A)I only
B)II only
C)III only
D)II and III only
E)I, II, and III are all true.

Question 9

Which of the following is a methylene group?

A)(-CH₂)
B)(=CH₂)
C)(-CH₂-)
D)(=CH=)
E)(-CH₃)

Question 10

Which is NOT true about n-alkanes?

A)Their formulas are all C_nH_2n2.
B)All the carbon atoms are centers of tetrahedral geometry.
C)Their melting points increase with the number of carbon atoms.
D)Their boiling points decrease with the number of carbon atoms.
E)All of the carbons are sp3 hybridized.

Question 11

Which of the following tends to be true of polymers but not small molecules?
I.variable rather than constant composition
II.melts over a range of temperatures poorly defined melting point)
III.solid state regions that are disordered

A)I
B)II
C)III
D)I, II, and III
E)None of these, as polymers are molecules just like small molecules, only bigger.

Question 12

A primary difference between branched chain alkanes and normal alkanes is

A)the ratio of hydrogen to carbon.
B)the number of hydrogen atoms bonded to nonterminal carbon atoms.
C)the orbital hybridization of the carbon atoms.
D)the bond angles around each carbon atom.
E)the degree to which electrons are delocalized.

Question 13

Iso-octane has the following structure.In this structure, how many carbon atoms are bonded to only two other carbon atoms?

A)0
B)1
C)2
D)3
E)4

Question 14

The -CH₃ unit is known as

A)a methyl group.
B)a methylene group.
C)an acetylene group.
D)an alkyne group.
E)an alkene group.

Question 15

Which pair shows two different molecules?

A)CH₃CH₂)₂CCH₃)₃
B)
C)
D)CH₃)₂CHCHCH₃)CHCH₃)₂
E)

Question 16

A subunit of an organic compound that confers particular chemical and physical properties to that compound is termed

A)a monomer.
B)an oligomer.
C)a functional group.
D)a synthetic unit.
E)an isomer.

Question 17

Determine the number of carbons in the longest chain for the following molecule.

A)6
B)7
C)8
D)9
E)10

Question 18

What is the molecular formula for the compound illustrated below?

A)C₅H₈
B)C₅H₉
C)C₅H₁₀
D)C₅H₁₁
E)C₅H₁₂

Question 19

Which of the following molecules would NOT be considered "organic"?

A)CaC₂
B)CH₃NH₂
C)(CH₃)₂O
D)NaCH₃(CH₂)₄COO
E)(NH₂)₂CO

Question 20

Which of the following is true about normal alkanes?

A)They all exhibit strong hydrogen bonding with one another and with water.
B)Some are gases, some are liquids, and some are solids at room temperature.
C)They all contain carbon, hydrogen, and oxygen in consistent ratios.
D)They all contain at least one double bond.
E)They all have the formula C_nH_2n.

Question 21

In a hydrogenation experiment, 50.00 grams of a straight-chain hydrocarbon containing 8 carbon atoms reacts with 1.829 grams of hydrogen gas.The hydrocarbon probably has the chemical formula

A)C₈H₁₈.
B)C₈H₁₆.
C)C₈H₁₄.
D)C₈H₁₀.
E)Insufficient information is provided.

Question 22

Name the compound with the structural formula CH₃(CH₂)₁₆CH₃.

A)n-octane
B)n-hexadecane
C)n-octadecane
D)n-decane
E)1,16-dimethylhexadecane

Question 23

What is the degree of unsaturation of the following molecule?

A)1
B)2
C)3
D)4
E)5

Question 24

Crude oil is composed mostly of

A)liquefied carbon.
B)liquefied rock and soil.
C)compounds composed of carbon and liquid alkanes.
D)decomposed anaerobic bacteria.
E)compounds composed of carbon, hydrogen, oxygen, and nitrogen.

Question 25

Cyclic alkanes differ from normal alkanes in

A)the ratio of hydrogen to carbon.
B)their utility as a combustible fuel.
C)the orbital hybridization on the carbon atoms.
D)the number of hydrogens bonded to nonterminal carbon atoms.
E)the number of double bonds.

Question 26

What is the molecular formula for the following compound?

A)C₆H₁₁
B)C₆H₁₂
C)C₇H₁₁
D)C₇H₁₂
E)C₇H₁₄

Question 27

Most simple ionic compounds that are soluble in water are not soluble in organic solvents.However, replacing a common cation such as Na⁺ with an alkyl ammonium ion with four alkyl groups greatly enhances solubility of the ionic compound in many organic solvents.Which formula represents the tetrabutylammonium ion that is found in tetrabutylammonium bromide?

A)[CH₃)₄N]⁺
B)[CH₃CH₂)₄N]⁺
C)[CH₃CH₂)₂)₄N]⁺
D)[CH₃CH₂)₃)₄N]⁺
E)[CCH₃)₃NH₂]⁺

Question 28

What is the formula for n-nonane?

A)CH₃(CH₂)₉CH₃
B)CH₃(CH₂)₁₇CH₃
C)CH₃(CH₂)₇CH₃
D)CH₃(CH₂)₅CH₃
E)CH₃(CH₂)₈CH₃

Question 29

When 1 mol of an alkyne with two degrees of unsaturation is hydrogenated, how many moles of hydrogen gas react?

A)0 mol
B)1.5 mol
C)0.5 mol
D)1.0 mol
E)2.0 mol

Question 30

What is the degree of unsaturation of the following molecule?

A)1
B)2
C)3
D)4
E)5

Question 31

Of an unknown compound containing only carbon and hydrogen, 0.123 moles was found to stoichiometrically react with 0.246 moles of hydrogen gas.Based on these data, we know that the unknown compound must be

A)an alkane.
B)an alkene.
C)an alkyne.
D)either an alkane or an alkene.
E)either an alkene or an alkyne.

Question 32

Which of the following is NOT likely to be a component of a natural gas deposit?

A)CH₄
B)C₃H₈
C)C₄H₈
D)C₄H₁₀
E)C₈H₁₈

Question 33

A compound composed solely of carbon and hydrogen that is unsaturated must be______ .Choose the best answer.

A)an alkane
B)an alkene
C)an alkyne
D)either an alkane or an alkene
E)either an alkene or an alkyne

Question 34

A saturated compound composed solely of carbon and hydrogen must be

A)an alkane.
B)an alkene.
C)an alkyne.
D)either an alkane or an alkene.
E)either an alkene or an alkyne.

Question 35

What is the systematic name of the molecule shown?

A)2,2,3,4-tetramethylpentane
B)2,3,4,4-tetramethylpentane
C)1,2,3,4,4-pentamethylbutane
D)1,1,1,2,3,3-hexamethylpropane
E)2-tert-butyl-3-methylbutane

Question 36

Which of the following statements regarding alkenes and alkynes is NOT correct?

A)Alkenes and alkynes are typically present in large amounts in crude oil.
B)Alkenes are commonly derived from plant sources.
C)Alkynes are not common in nature due to the reactivity of the CC bond.
D)Alkenes and alkynes can be hydrogenated to give alkanes.
E)Hydrocarbon reactivity increases in the order alkanes $\lt$ alkenes $\lt$ alkynes.

Question 37

What is the systematic name of the molecule shown?

A)3-methyl-5-butylheptane
B)2,4-diethyloctane
C)2-methyl-4-ethylhexane
D)3-methyl-5-ethylnonane
E)4-ethyl-7-methylnonane

Question 38

What is the systematic name of the molecule shown?

A)4-methyl-5-isopropylheptane
B)3-propyl-4-methylheptane
C)2-methyl-3,4-diethylpentane
D)2,4-dimethyl-3-ethylheptane
E)3-ethyl-2,4-dimethylheptane

Question 39

Which of the following statements regarding the reactions of alkanes, alkenes, and alkynes is NOT correct?

A)The electrons in the $\pi$ bonds of alkenes and alkynes are more likely to react than electrons in the $\pi$ bonds in alkanes.
B)Alkenes and alkynes readily undergo addition reactions with molecules such as HCl, HBr, and HI.
C)An example of an addition reaction involving an alkene is H₂C = CH₂ +HCl $\rightarrow$ H₃C-CH₂Cl.
D)Alkenes and alkynes are important intermediates in the syntheses of other organic molecules.
E)Alkanes readily undergo addition reactions with highly reactive molecules such as F₂.

Question 40

Of an unknown compound containing only carbon and hydrogen, 0.123 moles of the compound was found to stoichiometrically react with 0.123 moles of hydrogen gas.Based on these data, we know that the unknown compound must be

A)an alkane.
B)an alkene.
C)an alkyne.
D)either an alkane or an alkene.
E)either an alkene or an alkyne.

Question 41

Name the compound.

A)3-methyl-6-heptene
B)5-ethyl-1-hexene
C)5-methyl-1-heptene
D)2-ethyl-5-hexene
E)3-methylpentylethylene

Question 42

Do carbon atoms in aromatic hydrocarbon molecules not ions) obey the octet rule?

A)No, each carbon is bonded to only three atoms, and there are no lone pairs.
B)No, each carbon has one single bond and one double bond for a total of only six electrons.
C)Yes, each carbon obeys the octet rule.
D)Yes, but only because the double bond is counted twice owing to the resonance structures.
E)Yes, but only when one or the other resonance form dominates, not when the structure is an average of the two.

Question 43

Are the methyl groups in xylene, C₆H₄(CH₃)₂, included in the aromatic part of the molecular structure?

A)Yes, the aromatic bonding extends throughout the molecule.
B)Yes, but only when the resonance form with double bonds to the methyl groups exists.
C)No, only the carbons in the ring are involved in the aromatic system.
D)No, only the hydrogens in the ring are involved in the aromatic bonding.
E)No, only the carbon atoms in xylene are involved in aromatic bonding, not the hydrogens.

Question 44

Consider the 1,2-dichloro derivative of ethylene in which two of the hydrogen atoms on one of the carbon atoms in ethylene is substituted with a chlorine atom, giving the structural formula CH₂=CCl₂.Does this molecule have cis-trans isomers? Remember that ethylene does not.

A)yes, because the chlorines can be placed on the same or opposite sides of the double bond
B)yes, because the chlorines are placed on a single carbon
C)no, because both the formula and bonds are the same in all skeletal structures
D)no, because the two structures can interconvert through bond rotation
E)no, because there are less than four atoms bound to each carbon

Question 45

Which of the following statements regarding polymers is NOT correct?

A)Polymers often do not have a sharp melting point.
B)Polymers cannot contain double bonds because they are too reactive.
C)Branched-chain polymers tend to be more flexible than straight-chain polymers.
D)Straight-chain polymers tend to have higher densities than branched-chain polymers.
E)Heteroatoms in polymers can drastically change the properties of a hydrocarbon polymer.

Question 46

For each of the numbered bonds in the figure below, identify whether the bond is cis, trans, or neither cis nor trans.

A)I-cis; II-trans; III-cis
B)I-trans; II-cis; III-trans
C)I-neither; II-trans; III-cis
D)I-neither; II-cis; III-trans
E)I-neither; II-cis; II-cis

Question 47

Where is the carbon-carbon double bond in the hydrocarbon shown?

A)on the left
B)in the middle
C)on the right
D)on each bond
E)spread over all three bonds because of resonance

Question 48

Delocalized bonding in aromatic hydrocarbons is possible because of

A)the fact that electrons can move very quickly from one resonance form to another.
B)adjacent 2p_z orbitals each having one electron.
C)Wade's rules.
D)double-headed arrows.
E)Cooper pairs.

Question 49

Does this molecule have both cis and trans isomers?

A)Yes, this is the cis isomer.
B)Yes, this is the trans isomer.
C)No, it has only the cis isomer.
D)No, it has only the trans isomer.
E)No, this molecule does not have cis-trans isomerism.

Question 50

Name the compound.Note: Double and/or triple bonds are not shown.

A)1-butene
B)1-butyne
C)2-butene
D)2-butyne
E)butane

Question 51

How many structural constitutional) isomers are there for propylene, and why?

A)two, because of resonance
B)two, because of geometrical isomerism
C)two, because the double bond can be in either one of two locations
D)none, because the two possible skeletal structures can be superimposed
E)none, because double bonds always occur on the right in alkenes

Question 52

Is cyclooctatetraene considered aromatic? The most stable structure at room temperature is shown.

A)Yes, because there are alternating single and double carbon-carbon bonds.
B)Yes, because the electrons in the $\pi$ bonds are delocalized over the ring structure.
C)Yes, there is an even number of electrons involved in $\pi$ bonding.
D)No, the electrons in the $\pi$ bonds are not delocalized over the ring structure.
E)No, the carbons are not sp2 hybridized.

Question 53

Which of the following is/are true regarding aromatic hydrocarbons?
I.They are particularly stable because of delocalized bonding.
II.They are particularly stable because of their covalent network bonding.
III.They are particularly unstable, as evidenced by their tendency to evaporate.

A)I only
B)II only
C)III only
D)I and II only
E)I and III only

Question 54

Which of the following is NOT a difference between cyclohexane and benzene?

A)Cyclohexane is puckered, but benzene is planar.
B)Cyclohexane carbons are sp3 hybridized, but benzene carbons are sp2 hybridized.
C)Cyclohexane is not aromatic, but benzene is.
D)Cyclohexane has 12 hydrogen atoms in its structure, but benzene has 6 hydrogen atoms in its structure.
E)Cyclohexane is a combustible hydrocarbon, but benzene is not combustible due to aromaticity.

Question 55

Consider the 1,2-dichloro derivative of ethylene in which one of the hydrogen atoms on each of the two carbon atoms in ethylene is substituted with a chlorine atom, giving the structural formula CHClCHCl.Which of the following is true?

A)The trans isomer is more polar.
B)The cis isomer is more polar.
C)Neither cis nor trans isomers are polar.
D)Both cis and trans isomers are equally polar.
E)There are no isomers for this molecule.

Question 56

A homopolymer is a polymer in which

A)each polymer has the same mass.
B)each polymer has the same mass and structure.
C)the monomers are distributed uniformly throughout the polymer.
D)the polymers are distributed uniformly throughout the solution.
E)there is only one type of monomer unit.

Question 57

Name the compound.

A)trans-3-hexene
B)cis-3-hexene
C)trans-4-hexene
D)cis-4-hexene
E)1,2-diethylethylene

Question 58

Which of the following pairs show constitutional isomers?
I.
II.
III.
IV.

A)I
B)II
C)I and III
D)II and III
E)IV

Question 59

Name the compound.

A)cis-3-octene
B)trans-3-octene
C)cis-5-octene
D)trans-5-octene
E)1-ethyl-2-butyl ethylene

Question 60

Naphthalene, a polyaromatic hydrocarbon, is used for mothballs.Its molecular formula is C₁₀H₈.How many fused aromatic rings does naphthalene have in its molecular structure?

A)1
B)2
C)3
D)4
E)5

Question 61

The Aldrich Chemical Company catalogue lists the three isomers of xylene as having boiling points of 143-145C, 138-13911eed930_22f1_bf38_a0ba_a9cce94f9837_TB6562_11C, and 13811eed930_22f1_bf38_a0ba_a9cce94f9837_TB6562_11Which isomer has the highest boiling point, and why?

A)o-xylene (1,2-dimethylbenzene) because of its polarity
B)p-xylene (1,4-dimethylbenzene) because of its polarity
C)p-xylene (1,4-dimethylbenzene) because of its para-normalcy
D)m-xylene (1,3-dimethylbenzene) because of its C₂ symmetry
E)o,m,p-xylene( 1,2,3,4-tetramethylbenzene) because of its molar mass

Question 62

The C - O - H bonding arrangement is called the ______functional group.

A)alcohol
B)ester
C)amine
D)ether
E)carbonyl

Question 63

How many structural isomers does xylenol, (CH₃)₂C₆H₃OH, have?

A)None-there is only 1 molecule.
B)2
C)4
D)6
E)8

Question 64

What functional group is found in the following molecule?

A)amine
B)amide
C)ammonia
D)ammonium
E)amonyl

Question 65

How many structural isomers does xylene, C₆H₄(CH₃)₂, have?

A)None-there is only 1 structure.
B)2
C)3
D)4
E)5

Question 66

What is another name for methylbenzene?

A)toluene
B)xylene
C)naphthalene
D)benzoyl methane
E)1-methyl-2,4,6-cyclohexene

Question 67

Which of the following is an amine functional group?

A)(-COOH)
B)(-OH)
C)(-CN)
D)(-NH₂)
E)(-CONH₂)

Question 68

Which of the following is NOT a product when bacteria of the genus Methanosarcina act on amines? If all the compounds listed are products of the reaction, select E.

A)ammonia, NH₃
B)methane, CH₄
C)hydrogen cyanide, HCN
D)carbon dioxide, CO₂
E)All of these compounds are products of the reaction.

Question 69

Methane used for fuel and commonly called natural gas is odorless, but for safety it has a small quantity of foul-smelling methylmercaptan CH₃SH) added.The "mercaptan" functional group is most similar to which of the following?

A)carboxylic acid
B)amine
C)ether
D)aldehyde
E)alcohol

Question 70

What functional group is found in oil of peppermint?

A)carboxylic acid
B)aldehyde
C)alcohol
D)carbonyl
E)hydroxyl

Question 71

The molecular structure of thalidomide is shown below.Nitrogen II could be classified as a(n)_______ amine.

A)aromatic
B)auxiliary
C)primary
D)secondary
E)tertiary

Question 72

What type of amine is adrenaline, which is depicted below?

A)aromatic
B)auxiliary
C)primary
D)secondary
E)tertiary

Question 73

The characteristic "fishy" odor comes from methylamine (CH₃NH₂), which is similar to ammonia (NH₃) in structure and also in its ability to react with acids as a weak base.Why would the acid form of methylamine NOT have as strong an odor as methylamine?

A)because it would decompose to methane and ammonia
B)because it would not be volatile, being a polyatomic ion
C)because it would melt in the acid
D)because it would decompose to carbon, hydrogen, and nitrogen
E)because it would have a different three-dimensional structure

Question 74

How many structural isomers does toluene, C₆H₅CH₃, have?

A)None-there is only 1 molecule.
B)2
C)3
D)4
E)5

Question 75

The monomer for polystyrene is shown below.Which of the bonds is involved in the polymerization process?

A)I only
B)II only
C)III only
D)IV only
E)Bonds I-IV are all involved in polymerization.

Question 76

Gasoline additives such as ethanol are employed to

A)decrease odor.
B)promote complete combustion.
C)decrease octane rating.
D)make the fuel less volatile.
E)increase fuel value.

Question 77

Which of the following molecules, all of which contain at least one alcohol functional group, would you predict is the least soluble in water?

A)vitamin C,


B)glycerol,


C) $\alpha$ -D-glucose,
D)cholesterol,
E)adrenaline,

Question 78

The molecular structure of caffeine is shown below.The nitrogen atoms could be classified as _____amines.

A)primary
B)secondary
C)tertiary
D)auxiliary
E)aromatic

Question 79

Which of the following class of compounds is NOT generally used in gasoline?

A)alcohols
B)ethers
C)carboxylic acids
D)alkanes
E)thiols

Question 80

The molecular structure of thalidomide is shown below.Nitrogen I could be classified as a(n)_____ amine.

A)tertiary
B)secondary
C)primary
D)aromatic
E)auxiliary