Deck 10: An Introduction to Organic Chemistry

Question 1

Which alkyl group is a secondary alkyl group?

A)
$\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } -$
B)

C)

D)

E)All of these are correct.

Answer 1

Question 2

Which type of compound is NOT classified as an aliphatic hydrocarbon?

A)alkyne
B)aromatic
C)cycloalkane
D)alkene
E)alkane

Answer 2

aromatic

Question 3

Which of the following is 1-chloro-3-methylbutane?

A)

B)

C)

D)

E)

Answer 3

Question 4

Which statement concerning the two compounds shown below is FALSE?

A)Compound A and compound B are both organic compounds.
B)Compound A and compound B are both hydrocarbons.
C)Compound B has stronger intermolecular forces than compound A.
D)Compound A is likely a gas at room temperature and compound B is likely a liquid at room temperature.
E)Compound B has a higher boiling point than compound A.

Question 5

Which bonding pattern is NOT typical of carbon atoms in organic compounds?

A)

B)

C)

D)

E)

Question 6

The carbonyl group is a functional group found in many different types of compounds.What is the general structure of the carbonyl group?

A)

B)

C)

D)

E)

Question 7

Which of the following compounds would be named 3-ethyl-2-methylhexane?

A)

B)

C)

D)

E)(CH₃)₂CHCH₂CH₂(CH₂CH₃)₂

Question 8

Benzene may be represented by the line formula below.What is the molecular formula of benzene?

A)C₁₂H₆
B)C₆H₁₂
C)C₆H₆
D)C₆H₁₄
E)C₆

Question 9

Which correctly describes the geometry and bond angles around the indicated carbon in the structure below?

A)trigonal planar; 120°
B)tetrahedral,109.5°
C)trigonal pyramidal,109.5°
D)tetrahedral,90°
E)tetravalent,120°

Question 10

Which compound is classified as an ether?

A)

B)

C)
$\mathrm { CH } _ { 3 } - \mathrm { CH } _ { 2 } - \mathrm { O } - \mathrm { H }$
D)
$\mathrm { CH } _ { 3 } - \mathrm { CH } _ { 2 } - \mathrm { O } - \mathrm { CH } _ { 3 }$
E)
$\mathrm { CH } _ { 3 } - \mathrm { CH } _ { 2 } - \mathrm { NH } _ { 2 }$

Question 11

The functional group shown below is found in what type of compound?

A)alcohols
B)ketones
C)carboxylic acids
D)esters
E)aldehydes

Question 12

Which of the following best describes molecules related as conformational isomers?

A)same molecular formulas but different bonding patterns between atoms
B)different molecular formulas but the same connections between atoms
C)same molecular formulas,the same connections between atoms,but different spatial arrangement of atoms due to rotation around bonds
D)same molecular formulas but different cis-trans arrangement of atoms
E)different molecular formulas and different bonding patterns

Question 13

Consider the compound 4-ethyl-2,2-dimethylhexane,shown below.What classification best describes the fourth carbon atom in this six-carbon parent chain?

A)primary
B)secondary
C)tertiary
D)quaternary
E)It is impossible to determine without knowing the structural formula.

Question 14

What is the classification of the carbon atom that is bonded to the -OH group in menthol?

A)primary
B)secondary
C)tertiary
D)quaternary
E)pentary

Question 15

What is the name of the compound whose condensed formula is CH₃(CH₂)₅CH₃?

A)propane
B)pentane
C)hexane
D)heptane
E)1,5-dimethylpentane

Question 16

Which of the following is NOT a characteristic associated with undecane,an 11-carbon straight chain alkane?

A)hydrogen bonding
B)low water solubility
C)density less than water
D)flammable liquid
E)nonpolar

Question 17

An alkane used as a lubricant contains 25 carbon atoms.How many hydrogen atoms are present in its structure?

A)25
B)27
C)50
D)52
E)It is impossible to predict.

Question 18

How does an alkyl group differ from its parent alkane?

A)An alkyl group has a larger structure than its parent alkane.
B)An alkyl group contains one more hydrogen atom than its parent alkane.
C)An alkyl group contains one less carbon atom than its parent alkane.
D)An alkyl group contains one less hydrogen atom than its parent alkane.
E)There is no difference between an alkyl group and its parent alkane.

Question 19

Which of the following statements about organic compounds is FALSE?

A)Organic compounds are only synthesized by living systems.
B)Organic compounds are carbon-containing compounds.
C)Organic compounds contain covalent bonds.
D)The carbon atoms in organic compounds may be arranged in chains or rings.
E)Structural subunits called functional groups are responsible for the chemical behavior of organic compounds.

Question 20

The structure of an organic compound may be represented in several different ways.Which formula for an organic compound explicitly shows all of the atoms and bonds in a molecule?

A)molecular formula
B)condensed formula
C)structural formula
D)patterned formula
E)line formula

Question 21

The large number of organic compounds is due in part to the ability of these compounds to form constitutional isomers.Which of the following pairs of compounds are related as constitutional isomers?

A)

B)

C)

D)

E)

Question 22

The name of an organic compound is 2-methyl-4-propyloctane.What information about the structure of this compound is FALSE?

A)It is a branched alkane.
B)There are eight carbons in the parent chain.
C)There is a one-carbon alkyl group on carbon 2 of the parent chain.
D)There is a three-carbon alkyl group on carbon 4 of the parent chain.
E)None of the above statements is false.

Question 23

What is the molecular formula of the simplest alkane capable of having constitutional isomers?

A)CH₄
B)C₂H₆
C)C₃H₈
D)C₄H₁₀
E)C₅H₁₂

Question 24

A cycloalkane molecule contains 8 carbon atoms.How many hydrogen atoms are present in the molecule?

A)4
B)8
C)14
D)16
E)18

Question 25

The compound shown below can be made from the halogenation reaction of what compound?

A)propane
B)hexane
C)pentane
D)benzene
E)1-methylbutane

Question 26

What is the proper name for the compound shown below?

A)dimethylcyclohexane
B)trans-1,3-methylhexane
C)1-methyl-3-methyl-cis-cyclohexane
D)cis-1,3-dimethylcyclohexane
E)trans-1,3-dimethylcyclohexane

Question 27

What class of organic compounds contains the structure shown below?

A)aliphatic
B)isotopic
C)alkene
D)alkyne
E)aromatic

Question 28

Traces of chloroform,CHCl₃,were found in the trunk of a car of a Florida woman who was charged in the death of her child.Which of the following best represents the order of attachment of the atoms in chloroform?

A)

B)

C)

D)

E)None of the choices are correct.

Question 29

How does the molecular formula of a cycloalkane differ from that of the corresponding alkane?

A)The alkane has two fewer hydrogen atoms in its formula.
B)The cycloalkane has one fewer hydrogen atom in its formula.
C)The cycloalkane has one fewer carbon in its formula.
D)The cycloalkane has two fewer hydrogen atoms in its formula.
E)The alkane has two more carbon atoms in its formula.

Question 30

What is the structure of trans-1,3-dibromocyclohexane?

A)

B)

C)

D)

E)

Question 31

What type(s)of carbon-carbon bonds are never found in a saturated hydrocarbon?

A)single bonds
B)single and double bonds
C)double and triple bonds
D)single,double,and triple bonds
E)None of the choices are correct.

Question 32

Butanone (structure shown)may be classified as what type of compound?

A)aldehyde
B)ketone
C)ether
D)carboxylic acid
E)ester

Question 33

How many constitutional isomers are possible for the molecular formula C₅H₁₂?

A)one
B)three
C)four
D)five
E)six

Question 34

How do the different conformations of an alkane molecule arise?

A)through C-C bond cleavage
B)by rotation about C-C single bonds
C)through oxidation of C-C bonds
D)by rearrangement of the order of attachment of atoms in the molecule
E)by combustion and halogenation reactions

Question 35

Which of the following statements concerning conformational isomers is FALSE?

A)Conformational isomers are different spatial arrangements of the same molecule,formed by rotation around single bonds.
B)Conformational isomers rapidly interconvert,and cannot be physically separated from each other.
C)The staggered and the eclipsed conformation are two types of conformational isomers of alkanes.
D)The staggered conformation is more stable than the eclipsed conformation,because in the staggered conformation electron repulsion is maximized.
E)The boat conformation and the chair conformation are two conformational isomers of cyclohexane; the chair conformation is the more stable of the two.

Question 36

The chair and boat conformations of cyclohexane are shown below.Which statement best explains why the chair conformation is more stable than the boat conformation?

A)The hydrogen atoms in the chair conformation are all staggered,which minimizes the repulsion of the bonding electrons.
B)The carbon atoms in the chair conformation are all eclipsed,which provides for the ideal bond angle of 109.5°.
C)The carbon atoms in the chair conformation are closer together than in the boat conformation,which provides for stronger C-C bonds.
D)The hydrogen atoms in the chair conformation are closer together than in the boat conformation,which provides for stronger C-H bonds.
E)The C-C bonds in the chair conformation are all staggered,which maximizes the energy of the molecule.

Question 37

What term is used to describe the various spatial arrangements of a molecule formed by rotation around C-C single bonds?

A)geometric isomers
B)conformations
C)constitutional isomers
D)enantiomers
E)structural isomers

Question 38

Which of the following properly describes constitutional isomers?

A)organic compounds with different molecular formulas
B)compounds with the same molecular formula,but a different order of attachment of atoms
C)compounds with the same molecular formula and order of attachment of atoms,but a different spatial arrangement of atoms
D)compounds with the same number of hydrogens,but a different number of carbons
E)compounds with the same number of carbons,but a different number of hydrogens

Question 39

Eicosane is the name of the organic compound with the condensed formula CH₃(CH₂)₁₈CH₃.What does the prefix "eicos" specifically indicate about the structure of this compound?

A)It is an alkane.
B)It is a saturated hydrocarbon.
C)It contains a straight chain of carbons.
D)It is aliphatic.
E)It contains 20 carbons in a continuous chain.

Question 40

What additional condition or reagent is necessary for methane to react with chlorine according to the reaction equation shown below? CH₄ + Cl₂ → CH₃Cl + HCl

A)enzyme
B)water
C)light or high temperature
D)acid or base
E)complete darkness

Question 41

What is the IUPAC name of the following compound?

A)2-bromo-2-methylpropane
B)2-bromoisobutane
C)2,2-dibromomethylpropane
D)2-methyl-2-bromopropane
E)bromomethylbutane

Question 42

What is the correct classification for the compound shown below?

A)alcohol
B)aldehyde
C)carboxylic acid
D)ester
E)ketone

Question 43

In 1828,Friedrich Wöhler carried out the first synthesis of an organic compound from inorganic substances.What compound did he accidentally make?

A)glucose
B)urea
C)ammonium cyanate
D)aspirin
E)formaldehyde

Question 44

Which of the following is NOT a typical property of inorganic compounds?

A)high boiling point
B)flammable
C)water-soluble
D)rapid reactions
E)high melting point

Question 45

The reaction shown below can be used to prepare alkyl halides.Which of the following best describes the type of reaction illustrated?

A)addition
B)substitution
C)elimination
D)combustion
E)condensation

Question 46

What is the balanced equation for the complete combustion of cyclooctane?

A)C₈H₁₈ + 12O₂ → 8CO₂ + 9H₂O
B)C₈H₁₆ + O₂ → CO₂ + H₂O
C)2C₈H₁₂ + 24O₂ → 16CO₂ + 12H₂O
D)C₈H₁₆ + 12O₂ → 8CO₂ + 8H₂O
E)C₈H₁₆ + 8O₂ → 8CO + 8H₂O

Question 47

Which compound is NOT an isomer with the molecular formula C₅H₁₂?

A)

B)

C)

D)

E)All of these are correct.

Question 48

What functional groups are shown below?

A)alkoxy,amino
B)carbonyl,aldehyde
C)hydroxyl,ammonia
D)carbonyl,amino
E)None of the choices are correct.

Question 49

Functional groups are primarily responsible for the chemical properties of molecules in which they are found.Which of the following compounds have the same functional group,and would therefore have the same chemical properties?

A)A and D
B)B and C
C)B and D
D)A,B,and D
E)B,C,and D

Question 50

What is the IUPAC name of the following compound?

A)2,4,4-trimethylpentane
B)2,2,4-octane
C)2,2,4-trimethylpentane
D)trimethylpentane
E)None of the choices are correct.

Question 51

What is the source of most of the synthetic organic compounds that are used today?

A)methane
B)trees
C)petroleum
D)natural gas
E)coal

Question 52

What is the correct classification for the compound shown below?

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

Question 53

What is the molecular formula of butane?

A)C₃H₈
B)C₄H₈
C)C₄H₁₀
D)C₂H₆
E)None of the choices are correct.

Question 54

Which of the following is the condensed formula of 3-methylheptane?

A)CH₃CH₂CH(CH₃)CH₂CH₂CH₂CH₃
B)CH₃CH₂CH₂(CH₃)CH₂CH₂CH₂CH₃
C)CH₃CH(CH₃)CH₂CH₂CH₂CH₂CH₃
D)CH₃(CH₃)CHCH₂CH₂CH₂CH₃
E)None of the choices are correct.

Question 55

Which structural formula is represented by the condensed formula shown below? CH₂BrCH₂CH(CH₃)₂

A)

B)

C)

D)

E)

Question 56

What is the correct classification for the compound shown below?

A)alcohol
B)ether
C)amide
D)amine
E)alkene

Question 57

What is the IUPAC name of the compound below?

A)methylhexane
B)methylcyclohexane
C)toluene
D)hexylmethane
E)methylbenzene

Question 58

Which functional group is found in alcohols?

A)carboxyl
B)carboxy
C)amino
D)carbonyl
E)hydroxyl

Question 59

Which name describes a three-carbon alkane?

A)pentane
B)butane
C)propane
D)heptane
E)methane

Question 60

Methane reacts with oxygen in a combustion reaction to produce carbon dioxide and water.How many moles of water are produced by the complete combustion of one mole of methane?

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

Question 61

Which compound is an isomer of pentane?

A)2-methylpentane
B)ethylcyclopropane
C)2,2-dimethylpropane
D)cyclopentane
E)methylcyclobutane

Question 62

Molecules that have the same molecular formula,but have different structures are known as which of the following?

A)allotropes
B)isotopes
C)conformers
D)isomers
E)alkanes

Question 63

What is the IUPAC name of the following compound?

A)2-ethylbutane
B)2-methyl-2-ethylpropane
C)3-methylpentane
D)trimethylpropane
E)2-methyl-diethylmethane

Question 64

Which of the following is a possible product of the halogenation reaction shown below? $+\mathrm{Cl}_{2} \stackrel{\text { light }}{\longrightarrow}$

A)

B)

C)

D)

E)All of the compounds are possible products.

Question 65

What is the IUPAC name of the following compound?

A)3-ethylpentane
B)3-methylheptane
C)1,4-dimethylpentane
D)3-ethylheptane
E)2-methyl-diethylmethane

Question 66

Which of the following molecular formulas is not that of an alkane or cycloalkane?

A)C₆H₆
B)C₆H₁₂
C)C₅H₁₂
D)C₃H₆
E)C₃H₈

Question 67

Which equation properly represents the complete combustion of propane,C₃H₈?

A)C₃H₈ + 7O₂ → 3CO₂ + 8H₂O
B)C₃H₈ + 5O₂ → 3CO₂ + 4H₂O
C)C₃H₈ + 10O → 3CO₂ + 4H₂O
D)C₃H₈ + 7O → 3CO + 4H₂O
E)2C₃H₈ + 7O₂ → 6CO + 8H₂O

Question 68

Which compound is an isomer of 2-methylpropane?

A)2-chloropropane
B)2,2-dimethylpropane
C)propane
D)cyclobutane
E)butane

Question 69

Which is the correct order of melting points for the following alkanes,from highest temperature to lowest temperature?

A)nonane > hexane > methane > ethane
B)hexane > nonane > ethane > methane
C)nonane > hexane > ethane > methane
D)nonane > ethane > hexane > methane
E)methane > ethane > hexane > nonane

Question 70

What is the IUPAC name of the following compound?

A)dibromopentane
B)2,4-dibromopentane
C)2,4-dibromohexane
D)2,5-dibromohexane
E)1-bromo-2,5-methylbromopentane

Question 71

Which of the following compounds are related as geometric isomers?

A)1 and 2
B)1 and 3
C)1 and 4
D)2 and 3
E)All are related as geometric isomers.

Question 72

What word best describes the geometry (shape)around a carbon atom that has four single bonds to neighboring atoms?

A)tetrahedral
B)planar
C)regular
D)linear
E)unsaturated

Question 73

Which of the following is the monohalogenated product that results when cyclopentane undergoes chlorination according to the reaction below? $+ \mathrm { Cl } _ { 2 } \stackrel { \text { light } } { \longrightarrow }$

A)

B)

C)

D)

E)

Question 74

What is the IUPAC name of the following compound?

A)2,2-dimethylpropane
B)2-methylbutane
C)dimethylbutane
D)2-hydro-2-methylbutane
E)isopropylethane

Question 75

What is the IUPAC name of the following compound?

A)2,2-dimethylpropane
B)2-methylbutane
C)dimethylbutane
D)tetramethylethane
E)2,2,2-trimethylmethane

Question 76

Which compound is an isomer of 1,1-dibromoethane?

A)Br₂CHCH₃
B)CH₂BrCH₂Br
C)CH₃CHBr₂
D)CHBr₂CHBr₂
E)CH₃BrCH₃Br

Question 77

What is the name of the alkyl group represented by the structure below?

A)acetyl
B)dimethyl
C)propyl
D)ethanyl
E)ethyl

Question 78

Which compound is an isomer of butane?

A)cyclobutane
B)CH₃CH(CH₃)₂
C)benzene
D)CH₃CHBrCH₂CH₃
E)2,2-dimethylpropane

Question 79

What is the IUPAC name of the following compound?

A)2-chloromethane
B)2-chloropropane
C)1-methyl-1-chloroethane
D)1,1-chloromethylethane
E)2-chloroethane

Question 80

Of the structures shown,which are related as constitutional isomers?

A)1 and 3
B)2 and 3
C)3 and 4
D)Both 1 and 3 and 2 and 3 are correct.
E)1 and 3,2 and 3,and 3 and 4 are all related.