Download History of Organic Chemistry

Organic Chemistry Testbank
History of Organic Chemistry
The first organic chemical to be synthesized in a lab from inorganic chemicals was
a.
ethanol
c.
methane
b.
sugar
d.
urea
The first person to synthesis an organic chemical from inorganic chemicals was
a.
August Kekulé
c.
Friedrich Wöhler
b.
John Dalton
d.
Raymond LeMieux
The Avitalism@ theory in organic chemistry held that
a.
organic chemicals can only be obtained from living organisms
b.
organic chemicals can only be obtained from dead organisms
c.
organic chemicals can only be obtained from living or dead organisms
d.
organic chemicals can be obtained from any source of chemicals, organic or
inorganic.
Long Answer:
Explain why Wöhlers synthesis of urea by heating ammonium cyanate crystals was a landmark
event in the study of organic compounds.
Definition of Organic Chemistry
Organic chemicals
a.
are all the compounds of carbon including the ionic compounds
b.
are all the molecular compounds of carbon except the oxides
c.
are all the ionic compounds of carbon including the oxides
d.
can only be made by living organisms
Throughout history there have been many definitions of organic chemistry. The modern
definition of organic chemistry refers to the study of
a.
ionic compounds of carbon
b.
molecular compounds of carbon
c.
non-living substances only
d.
substances derived from living things.
Which is an organic chemical?
a.
CaCO3
c.
Cl2
b.
CCl4
d.
CO2
Which is NOT an organic chemical?
a.
CH3COOH
c.
C4H7O
b.
CO2
d.
CCl4
Which is NOT an organic chemical?
c.
CH3CHO
c.
C2H6O
d.
CBr4
d.
CO
Which substance is organic?
a.
AgCl
c.
NH4CN
b.
AgOCN
d.
(NH2)2CO
Multitude of Organic Chemicals
1
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Which statement is true?
a.
Carbon can bond in chains with branches, but cannot form rings
b.
Carbon can form single bonds, but not double and triple bonds.
c.
Carbon can bond in chains with branches, in rings, and with single, double and
triple bonds
d.
Carbon cannot form rings with double bonds or branches on them
Which statement is true?
a.
Over 90% of all known compounds are organic
b.
Over 90% of all known compounds are inorganic
c.
There are about 2 times as many inorganic compounds as organic compounds
d.
There are about 2 times as many organic compounds as organic compounds
There are thousands of times more organic than inorganic compounds. The enormous number of
carbon compounds is believed to be due, in large part, to the
a.
high bonding capacity of a carbon atom.
b.
ability of carbon atoms to form covalent bonds with hydrogen.
c.
high number of lone pairs of electrons of a carbon atom.
d.
large variety of chemical reactions of elemental carbon
Short Answer:
List three factors that contribute to the tremendous diversity of carbon compounds relative to the
number of inorganic compounds.
Give two (good) reasons why carbon has its own branch of chemistry.
Homologous Series
Each member of the alkane series differs from the preceding member by one additional carbon
atom and
a.
1 hydrogen atom
c.
2 hydrogen atoms
b.
3 hydrogen atoms
d.
4 hydrogen atom
The alkane family is referred to as a homologous series because each member of the family
a.
becomes more soluble in water as they get larger
b.
can have more isomers as they get larger
c.
has a boiling point that increases as they get larger
d.
increases by A-CH2" as they get larger
Which of the following is part of a homologous series:
a.
CH4, C2H4, C4H8
b.
CH4, C2H2, C3H6
c.
C3H8, C3H6, C3H4
d.
C2H4, C3H6, C4H8
Which term describes this group of compounds?
chloromethane, chloroethane, 1-chloropropane, 1-chlorobutane
a.
aldehydes
c.
functional isomers
b.
aromatics
d.
homologous series
Alkanes/Straight chain alkanes
Alkanes are:
Organic Chemistry Testbank
3
a.
organic compounds containing one or more carbon-carbon double bonds
b.
special group of unsaturated cyclic hydrocarbons
c.
organic compounds containing one or more carbon-carbon triple bonds
d.
hydrocarbons that contain only single covalent bonds
How many double covalent bonds are in an alkane?
a.
none
c.
one
b.
two
d.
The number varies
How many carbons are in a molecule of hexane?
a.
3
b.
4
b.
5
d.
6
What is the name of the alkane having five carbons?
a.
hexane
c.
methane
b.
octane
d.
pentane
What increment of change occurs between propane and butane in the alkane series?
B
a.
-CHb.
-CH2b.
-CH3d.
-CH2=
Which of the following is a condensed structural diagram for propane?
H
H
H
a.
C3H8
H
C
C
C
H
b.
CH3-CH2-CH3
d.
c.
C-C-C
H
H
H
What is the name of the molecule on the right?
CH2
CH3
a.
butane
H
C
CH
b.
pentane
3
2
c.
propane
d.
tetrane
What is the name of the molecule on the right?
CH2
CH2
CH3
a.
butane
H3C
CH2
CH2
b.
pentane
c.
propane
d.
hexane
What is the IUPAC name of the compound on the right?
H
H
H
H
H
a.
butane
b.
decane
H
C
C
C
C
C
c.
propane
H
H
H
H
H
d.
pentane
What is the name of the straight chain alkane with 7 carbons?
a.
pentane
c.
hexene
b.
heptane
d.
octyne
Branched Alkanes - Nomenclature
Which condensed structural formula represents the alkyl group called ethyl?
a.
CHCH
c.
CH2CH3
H
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b.
CH2CH2
d.
CH3CH3
What is the name of an alkyl group that contains two carbon atoms?
a.
diphenyl
c.
dimethyl
b.
ethyl
d.
propyl
What prefix is used to represent the substituent CH3-CH2-CH2-?
a.
ethylc.
methylb.
propyld.
pentyl
If a substituent appears four times in an organic compound, what prefix is used?
a.
dic.
monob.
pentad.
tetraWhat is the name of the compound on the right?
a.
2,4-diethyl-2-methylhexane
b.
3-ethyl-5,5-dimethylheptane
c.
5-ethyl-3,3-dimethylheptane
d.
3,5-diethyl-5-methylhexane
What is the IUPAC name of compound on the right?
a.
2-ethyl-3-dimethylhexane
b.
2-ethyl-3,3-diemethylhexane
c.
4,4,5-trimethylheptane
d.
3,4,4-trimethylheptane
What is the IUPAC name of compound on the right?
a.
2,3-dimethylpentane
b.
3,4-dimethylpentane
c.
3,4,4 -trimethylbutane
d.
2,3,4-trimethylbutane
What is the IUPAC name of compound on the right?
a.
trimethylpentane
b.
2-methyl-3-methyl-4-methylpentane
c.
2,2-dimethyl-3-methylpentane
d.
2,3,4-trimethylpentane
H3C
CH3
CH
H3C
CH
What is the IUPAC name of compound on the right?
a.
2-ethyl-2,4,5-trimethylpentane
b.
2-ethyl-2,4-dimethylhexane
CH2 CH2 CH2
c.
3,5,5-trimethylheptane
CH3
d.
3,3,5-trimethylheptane
What is the correct IUPAC name for the compound shown below?
CH3.CH(CH2.CH3).CH(CH3)2
a.
2,3-dimethyl pentane
c.
1,1,2-trimethyl butane
b.
2-ethyl-3-methyl butane
d.
3,4-dimethyl pentane
Which is the condensed structural formula for 2,2,3-trimethylbutane?
CH
CH3
CH3
CH3
C
CH2
CH3
CH3
Organic Chemistry Testbank
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a.
CH3CH2(CH3)CH(CH3)2
c.
CH3C(CH3)2C(CH3)3
b.
CH3C(CH3)2CH(CH3)2
d.
CH3CH2CH(CH3)C(CH3)3
What is the IUPAC name for this compound? CH3CH(CH3)C(CH3)3.
a.
2,2,3-trimethylbutane
c.
tetramethylpropane
b.
1,1,1,2-tetramethylpropane
d.
heptane
Alkenes - Nomenclature
Alkenes are:
a.
organic compounds containing one or more carbon-carbon double bonds
b.
special group of unsaturated cyclic hydrocarbons
c.
organic compounds containing one or more carbon-carbon triple bonds
d.
hydrocarbons that contain only single covalent bonds
Which hydrocarbon contains a double carbon to carbon bond?
a.
1-butene
c.
2-methylbutane
b.
1-butyne
d.
cyclobutane
Which compound is an alkene?
a.
butyne
c.
pentane
b.
nonene
d.
propanone
What is the name of the molecule on the right?
CH2
CH3
a.
2-ethyl-3-propyl-1-pentene
b.
2,3-diethyl-4-methyl-1-pentene
CH3 CH2 C
CH CH CH3
c.
3-ethyl-2,4-dimethyl4-hexene
CH2
d.
3,4-diethyl-2-methyl-4-pentene
What is the name of the molecule on the right?
CH2 CH CH3
3
a.
2,3-dimethyl-4-propyl-4-pentene
CH3 CH2 CH2 C
CH CH CH3
b.
2,3-dipropyl-1-butene
c.
3,4-dimethyl-2-propyl-1-pentene
CH3
d.
4,5,6-trimethyl-4-heptene
What is the IUPAC name of this compound?
H
H
H
a.
1,1-dimethyl-2-butene
b.
2-methyl-3-pentene
H
C
C
H
C
H
c.
4-methyl-2-pentene
C
C
H
d.
methylhexane
H
H
H
C
H
H
According to the rules established by chemists, what is the IUPAC name of the compound on the
right?
CH3
a.
1-methyl-1-pentene
b.
5-methyl-4-pentene
HC
CH CH2 CH2 CH3
c.
2,3-hexene
d.
2-hexene.
Determine the IUPAC name for the following molecule:
Organic Chemistry Testbank
a.
b.
c.
d.
6
2,5-dimethyl-2-hexene
2,5-dimethyl-4-hexene
2,5-dimethyl-2-heptene
2,5-dimethyl-4-heptene
What is the name for the following molecule?
H3C
CH2
CH3
a.
2-ethyl-2-pentene
C
C
b.
4-ethyl-3-pentene
c.
3-methyl-3-hexene
H
CH2 CH3
d.
4-methyl-3-hexene
The correct name for the compound (CH3)2CH.CH(CH3).CH2.CH:CH2 is:
a.
4,5,5-trimethyl-1-pentene
b.
4,5-dimethyl-1-hexene
c.
2,3-dimethyl-5-hexene
d.
4-propyl-4-methyl-1-butene
Alkynes - Nomenclature
Alkynes are:
a.
organic compounds containing one or more carbon-carbon double bonds
b.
special group of unsaturated cyclic hydrocarbons
c.
organic compounds containing one or more carbon-carbon triple bonds
d.
hydrocarbons that contain only single covalent bonds
What is the name of the smallest alkyne?
a.
butyne
c.
ethyne
b.
methyne
d.
propyne
CH2 CH3
What is the name of the molecule on the right?
a.
4,4-diethyl-2-butyne
H3C
C
C HC
b.
4-ethyl-2-hexyne
CH2 CH3
c.
3-ethyl-4-hexyne
d.
1,1-diethyl-2-butyne
What is the name of the molecule on the right?
a.
1,6,6,6-tetramethyl-2-pentyne
b.
2,2-dimethyl-4-heptyne
c.
2,2,6-trimethyl-4-hexyne
d.
6,6-dimethyl-3-heptyne
CH3
H3C
H3C
HC
C
CH
CH
CH2
CH2
H3C
CH3
C
C
CH3
Which is the condensed structural diagram for 4-methyl-2pentyne?
a.
CH2 C
CH3
c.
H3C
C
C
CH3
Organic Chemistry Testbank
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CH3
CH3
CH
b.
H3C
CH
CH
CH
CH3
H3C
C
What is the name of the molecule
a.
acetylene
b.
1-butyne
Cycloalkanes, cylcoalkene - Nomenclature
d.
CH
c.
d.
H2C
CH
CH2
CH3
?
propyne
propene
What is the name of the molecule on the right?
a.
ethylbenzene
b.
ethylcyclohexane
c.
phenylethane
d.
propylcyclohexane
What is the name of the molecule on the right?
a.
butylcyclohexane
b.
phenylpropane
c.
propylbenzene
d.
propylcyclohexane
What is the name of the molecule on the right?
a.
ethylcyclopentane
b.
pentylcyclopropane
c.
propylcylclopentane
d.
propylcyclohexane
What is the name of the molecule on the right?
a.
2-ethylcyclopentene
b.
3-ethylcyclopentene
c.
2-ethyl-2-cyclopentene
d.
5-ethyl-2-cyclopentene
What is the name of the molecule on the right?
a.
2-methylcyclohexene
b.
3-methylcyclohexene
c.
4-methylcyclohexene
d.
5-methylcyclohexene
CH3
Select the proper order of stability from least to most stable for the following cycloalkenes:
Organic Chemistry Testbank
B
A
a.
b.
8
C
A, B, C
B, C, A
c.
d.
C, A, B
C, B, A
Simple Aromatics - nomenclature
What is the name of the molecule on the right?
a.
2-butylbenzene
b.
butylbenzene
c.
phenylbutane
d.
propylbenzene
What is the name of the molecule on the right?
a.
butylbenzene
b.
2-pentylbenzene
c.
pentylbenzene
d.
phenylpentane
What is the IUPAC name of the compound on the right?
a.
pentylcyclohexane
b.
cyclopentylhexane
c.
pentylbenzene
d.
hexylbenzene
What is the IUPAC name of the compound on the right?
a.
butylbenzene
b.
phenylbutane
c.
propylbenzene
d.
phenylpropane
CH2
CH2
CH2
CH2
CH3
CH2
CH2
CH3
CH2
Phenyl Branches - nomenclature
What is the IUPAC name of the molecule on the right?
a.
1,1,4-trimethyl-4-phenylbutane
b.
2,4-dimethyl-5-phenylpentane
c.
2,4-dimethyl-2-pentylbenzene
d.
2,4-dimethyl-1-phenylpentane
What is the IUPAC name of the molecule on the right?
a.
2-methyl-3-ethyl-1-phenylbutane
b.
2,3-dimethyl-1-phenylpentane
c.
2,3-dimethyl-1-pentylbenzene
d.
3,4-dimethyl-5-phenylpentane
CH2
CH2
CH3
CH
CH
CH3
CH3
CH2
CH3
CH
CH
H3C
CH3
CH2
Organic Chemistry Testbank
9
What is the IUPAC name for the molecule on the right?
a.
2-pentylbenzene
b.
2-phenypentane
c.
1 -methyl-1-phenylbutane
d.
pentylbenzene
How many phenyl groups does the following molecule have?
a.
0
c.
2
b.
1
d.
6
Disubstituted benzenes
What is another acceptable name for 1,3-dimethylbenzene?
a.
m-dimethylbenzene
c.
b.
n-dimethylbenzene
d.
What is another acceptable name for 1,4-dimethylbenzene?
a.
m-dimethylbenzene
c.
b.
n-dimethylbenzene
d.
What is another acceptable name for 1,2-dimethylbenzene?
a.
m-dimethylbenzene
c.
b.
n-dimethylbenzene
d.
What is the name of the molecule on the right?
a.
ethylmethylbenzene
b.
o-ethylmethylbenzene
c.
m-ethylmethylbenzene
d.
p-ethylmethylbenzene
What is the name of the compound on the right?
e.
diethylbenzene
f.
m-diethylbenzene
g.
o-diethylbenzene
CH2 CH2
HC
CH3
CH3
o-dimethylbenzene
p-dimethylbenzene
o-dimethylbenzene
p-dimethylbenzene
o-dimethylbenzene
p-dimethylbenzene
CH3
H3C
h.
p-diethylbenzene
What is the name of the molecule on the right?
a.
ethylpropylbenzene
b.
o-ethylpropylbenzene
c.
m-ethylpropylbenzene
d.
p-ethylpropylbenzene
What is the IUPAC name for the isomeric compound on the right?
a.
1,2-dichlorobenzene
b.
1,3-dichlorobenzene
c.
2,2-dichlorobenzene
d.
2,6-dichlorobenzene
Which of the following molecules is p-ethylmethylbenzene?
Cl
Cl
Organic Chemistry Testbank
a.
10
b.
c.
d.
Units of Unsaturation/general formulas
What type of hydrocarbon is the compound on the right? CH3-CH2-CH2-CH2-CH2-CH3
a.
aliphatic
c.
cyclic
b.
aromatic
d.
unsaturated
Which hydrocarbon is saturated?
a.
C6H6
c.
C6H12
b.
C6H10
d.
C6H14
Which is the formula of a saturated hydrocarbon?
a.
C2H2
c.
C2H4
b.
C5H8
d.
C5H12
Which is the formula of a saturated hydrocarbon?
a.
CH2CH2
c.
C6H6
b.
CH3CHCH2
d.
(CH3)3CH
A saturated continuous-chain hydrocarbon with seven carbons is _____.
a.
cycloheptene
c.
heptene
b.
heptane
d.
heptyne
Which of the following compounds is an unsaturated hydrocarbon?
a.
methane
c.
nonane
b.
propyne
d.
ethyl
How many units of unsaturation does the molecular formula C5H8 have?
a.
none
c.
two
b.
one
d.
three
How many units of unsaturation does the molecular formula C7H12 have?
a.
none
c.
two
b.
one
d.
three
Which could be a molecular formula for an organic chemical with one ring and one double bond?
a.
C5H10
c.
C5H8
b.
C6H14
d.
C6H12
Which could be a molecular formula for an organic chemical with one ring?
a.
C5H10
c.
C5H8
b.
C6H14
d.
C6H10
Organic Chemistry Testbank
Which could be a molecular formula for a non-cyclic hydrocarbon with two double bonds?
a.
C5H10
c.
C5H8
b.
C6H14
d.
C6H12
What is the molecular formula for 3,3-diethyl-4-methyl-1-hexyne?
a.
C10H18
c.
C11H22
b.
C11H20
d.
C12H22
Which formula represents a member of the alkene series?
a.
C3H6
c.
C2H2
b.
C2H6
d.
C6H6
Which formula represents a member of the alkane family?
a.
C3H6
c.
C2H2
b.
C2H6
d.
C6H6
What is the general formula for a continuous-chain alkane?
a.
CnHn
c.
CnH2n-2
b.
CnHn+2
d.
CnH2n+2
To which class of aliphatic hydrocarbons does C25H52 belong?
a.
alkanes
c.
alkynes
b.
alkenes
d.
aromatics
Which of the following molecules is a saturated hydrocarbon?
a.
b.
c.
d.
Isomers:
Which molecule is NOT an isomer of C4H8?
a.
b.
Which molecule is NOT an isomer of C5H12?
c.
d.
11
Organic Chemistry Testbank
a.
c.
b.
d.
C8H16 could have isomers with
a.
one ring or one double bond
c.
one ring and one double bond
b.
one triple bond
d
two rings
Which structural formula represents an isomer of 2-pentyne?
a.
c.
b.
d.
Which compound is an isomer of methylpropane?
a.
butane
c.
pentane
b.
cyclopropane
d.
propane
Which of the following compounds is a structural isomer of butane?
a.
2-methylbutane
c.
2,2-dimethylbutane
b.
2-methylpropane
d.
2,2-diethylpropane
Which pairs of molecules are structural isomers?
a.
cyclohexane and 2,2-dimethylbutane
b.
cyclohexene and 3,3-dimethyl-1-butyne
c.
methylcyclobutane and 2-pentyne
d.
2-methylpentyne and 2-methylpentene
A structural isomer of hexane is _____.
a.
benzene
c.
cyclohexane
b.
2,2-dimethylbutane
d.
2-methylpentene
Which compound can have isomers?
a.
C2H4
c.
C2H2
b.
C2H6
d.
C4H8
How many structural isomers exist for the alkene CH2Br2?
a.
1
c.
3
b.
b.
2
d.
4
Which compound is an isomer of CH3.CH2.CH2.CH2.OH
a.
CH3CH2OCH3
c.
CH3CH2CH2CH3
b.
CH3CH2CH2OH
d.
CH3CH(OH)CH2CH3
Which of the following pairs of compounds are isomers?
a.
diethyl ether and 1-butanol
b.
2-pentanone and 2-pentanol
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Organic Chemistry Testbank
c.
pentanal and methyl butanoate
d.
Structural isomers have _____.
a.
the same molecular formula
b.
different physical and chemical properties
c.
the same elemental composition
d.
all of the above
Which of the following pairs of compounds are isomers?
a.
propanal and 1-propanol
b.
propanoic acid and propyl propanoate
c.
propanone and propanal
d.
propyl ether and 1-propanol
Isomer - Short Answer
13
propanoic acid and propanal
1a)
A student is told to draw the structural diagram of the compound with formula C4H10 .
Confused, the student tells the naive chemistry-challenged person that the task is impossible.
a)
Why can=t the student show the structure of C4H10? (2)
b)
Rephrase the question by changing one word so that the question can be answered, and
then answer it. (Keep the flavor of the question - don't change it completely!) (4)
1a)
Give a brief explanation, using two examples, as to why the numbers are necessary for
identifying an organic compound sometimes, but not other times. (4)
b)
Identify which of the following names need numbers in front to identify them completely:
butanol, propanal, pentanone, hexene, butanoic acid, methylpentane.(3)
How many different answers should you get to the question, "What is the boiling point of
C3H8O?" Explain with the use of structural diagrams, names and a brief discussion of
intermolecular attractions.
Draw structural formulas for and name four isomers of C4H7Cl.
Halocarbons
Which substituent would allow a compound to be classified as an alkyl halide?
a.
fluorine
c.
oxygen
b.
nitrogen
d.
sulfur
The IUPAC name for the compound (CH3)2C(CH2.CH3).CH2.CHCl.CH3 is:
a.
5-chloro-3,3-dimethylhexane
c.
2-chloro-4-methyl-4-ethylpentane
b.
4-chloro-2-ethyl-2-methylpentane d.
1-chloro-1,3,3,3-trimethylpentane
What is the name of the molecule on the right?
Cl
CH3
a.
2-dichloro-3-methylpentane
b.
2,2-dichloro-3-methylpentane
CH3 C
CH CH2 CH3
c.
4,4-dichloro-3-methylpentane
d.
4,4-dichloro-3,5-dimethylbutane
Cl
What is the name of the molecule on the right?
CH3
a.
2,3-dichloro-2-methylpentane
CH3 C
Cl
CH
Cl
CH2 CH3
Organic Chemistry Testbank
b.
1,2-dichloro-1,1-dimethylbutane
c.
2,3-chloro-2-methylpentane
d.
3,4-dichloro-4-methylpentane
The correct name for the molecule on the right is:
a.
1,4,4-trifluoro-2-bromopentane
b.
2-bromo-1,4,4-trifluoropentane
c.
2,2,5-trifluoro-4-bromopentane
d.
4-bromo-2,2,5-trifluoropentane
14
Br
F
F
CH
C
CH2
CH2
H3C
F
Alcohols
What is the name of the molecule on the right?
H3C
CH2
a.
butanone
CH CH3
b.
2-butanol
c.
2-butanal
HO
d.
butyl ether
What is the name of the molecule on the right?
OH
a.
3-pentanone
b.
3-pentanal
H3C
CH
CH3
c.
3-pentanol
CH2
CH2
d.
pentanoic acid
What is the correct IUPAC name for the compound shown below?
CH3.CH2.CH(CH2.CH3).CH(OH).CH3
a.
3-ethyl-4-pentanol
b.
2-methyl-5-hexanol
c.
3-ethyl-2-pentanol
d.
3-ethyl-2-heptanol
The correct IUPAC name for the compound CH3.CH2.CH2.C(CH3)2.OH is
a.
1-hexanol
c.
1- dimethylbutanol
b.
1,1-dimethyl-1-butanol
d.
2-methyl-2-pentanol
Ethers
Which molecule is an ether?
OH
O
CH
a.
H3C
CH2
CH2
C
CH3
c.
CH3
CH3
CH
b.
H3C
H3C
O
CH2 C
CH2
O
CH2
O
CH3
d.
OH
CH3
Organic Chemistry Testbank
15
Which of the following is an ether?
OH
CH3 CH2
CH3 CH2 CH2 CH2 C
O
a.
O
c.
CH3
CH3
CH3 CH2 CH2 C
CH3 CH2 CH2 CH
O
b.
d.
What is the name of the molecule on the right?
a.
butanal
b.
methylpropyl ether
c.
butanone
d.
methyl propanoate
What is the name of the molecule on the right?
H3C
a.
pentanal
b.
ethylpropyl ether
c.
pentanone
d.
ethyl propanoate
O
O
CH2
CH3
O
CH2
CH2
CH2
CH2
CH3
Aldehydes
Which molecule is an aldehyde?
CH3
O
C
a.
O
CH2
CH2
C
CH3
c.
H3C
CH3
b.
CH3
O
CH
H3C
CH2
O
CH2
O
C
CH3
d.
CH2
H
CH2
Which of the following is an aldehyde?
OH
CH3 CH2
CH3 CH2 CH2 CH2 C
a.
O
c.
O
CH3
CH3
CH3
Organic Chemistry Testbank
16
CH3
CH3 CH2 CH2 C
CH3 CH2 CH2 CH
O
b.
O
d.
What is the IUPAC name of the molecule on the right?
a.
butanal
b.
1-butanone
c.
butanoic acid
d.
propanal
What is the IUPAC name of the molecule on the right?
a.
butanal
b.
1-butanone
c.
butanoic acid
d.
propanal
Which of the following is an aldehyde?
a.
butanone
c.
b.
ethanol
d.
Which of the following is an aldehyde?
a.
butanal
b.
c.
ethanol
d.
O
CH
CH2
CH2 CH3
O
CH
CH2
CH2 CH2
ethane
pentanal
ethanone
pentanoic acid
Ketones
What is the IUPAC name of the molecule on the right?
a.
ethylpropyl ether
b.
3-hexanal
c.
3-hexanone
d.
methyl butanoate
What is the IUPAC name of the molecule on the right?
a.
diethyl ether
b.
2-pentanone
c.
3-pentanone
d.
3-pentanal
Which of the following is a ketone?
O
O
OH
CH3 CH2
CH3 CH2 CH2 CH2 C
O
a.
c.
O
CH3
CH3
CH3 CH2 CH2 C
b.
CH3 CH2 CH2 CH
O
d.
CH3
O
Organic Chemistry Testbank
Which condensed structural formula represents a ketone?
a.
CH3CH2CH2OH
c.
b.
CH3CH2CHO
d.
17
CH3COCH3
CH3CH2COOH
Carboxylic Acids
What is the IUPAC name of the molecule on the right?
a.
butanone
b.
ethanoic acid
c.
methy propanoate
d.
propanoic acid
What is the IUPAC name of the molecule on the right?
a.
butanal
b.
butanoic acid
c.
methy propanoate
d.
propanoic acid
What is the IUPAC name of the molecule on the right?
a.
pentanal
b.
pentanoic acid
c.
methy butanoate
d.
pentanone
OH
O
HO
O
CH3
CH2 CH2
O
CH2 C
OH
Esters
What is the IUPAC name of the molecule on the right?
a.
butyl ethanoate
b.
ethyl propanoate
c.
ethyl butanoate
d.
propyl ethanoate
What is the IUPAC name of the molecule on the right?
a.
ethyl methanoate
b.
methyl ethanoate
c.
ethanoic acid
d.
propanoic acid
What is the IUPAC name of the molecule on the right?
a.
ethyl propanoate
b.
methyl butanoate
c.
butyl methanoate
d.
methyl propanoate
O
O
CH3 CH2
O
O
C
H
O
O
Trivial Names
What is the IUPAC name of the molecule on the right?
CH3
Organic Chemistry Testbank
a.
b.
c.
d.
18
acetylene
formaldehyde
phenol
toluene
What is the IUPAC name of the molecule on the right?
a.
acetylene
b.
formaldehyde
c.
phenol
d.
toluene
OH
Fractional Distillation/Sources of hydrocarbons
Which molecule would condense closer to the top of a fractional distillation tower?
a.
C5H12
c.
C14H30
b.
C10H22
d.
C20H42
Which molecule would condense closer to the bottom of a fractional distillation tower?
a.
C5H12
c.
C14H30
b.
C10H22
d.
C20H42
Which is the correct statement regarding fractional distillation?
a.
The mixture of hydrocarbons in crude oil are converted into the various fractions
(gasoline, furnace oil, etc.) by chemical reactions
b.
Substances with high boiling points will condense lower in the fractional
distillation tower.
c.
Fractions with very low boiling points will condense before the fractions with
high boiling points
d.
Crude oil from different sources, when distilled in a fractionating tower, will yield
the same percent of gasoline
Which compound in crude oil will be the first to evaporate relative to the other hydrocarbons
listed?
a.
decane
c.
heptane
b.
nonane
d.
octane
What is not a source of raw materials for petrochemical industries?
a.
coal deposits
c.
crude oil
b.
mineral deposits
d.
natural gas
What is the main hydrocarbon component of natural gas?
a.
benzene
c.
ethane
b.
methane
d.
propane
Which type of coal has the highest carbon content?
a.
anthracite
c.
lignite
b.
bituminous
d.
peat
Which process involves the conversion of once living organic matter to fossil fuels?
Organic Chemistry Testbank
a.
b.
carbonization
nuclear fusion
c.
d..
combustion
photosynthesis
Shapes of molecules
The bonding shape around every carbon in propane is
a.
bent
c.
tetrahedral
b.
linear
d.
trigonal planar
What is the shape of a methane molecule?
a.
bent
c.
pyramidal
b.
linear
d.
tetrahedral
The bonding shape around both carbons in ethyne is
a.
bent
linear tetrahedral
trigonal planar
Which of the following molecules is completely flat or planar?
a.
a. ethene
b. ethane
c. propene d. cyclohexane
Which description best describes the boding shape around the carbons in the molecule on the
right?
a.
trigonal planar
b.
linear
c.
tetrahedral
d.
cyclic
Short Answer:
1. (a) Draw Lewis diagrams for ethane and ethyne.
(b)
Describe the shape around the carbon atoms in ethane versus ethyne.
(c)
How does the shape and arrangement of bonding electrons influence the reactivity of
ethane versus ethyne?
Solubility
Which substance would be most soluble in water?
a.
propanoic acid
c.
propanal
b.
propanone
d.
propane
Which substance would be least soluble in water?
a.
propanoic acid
c.
propanal
b.
propanone
d.
propane
Which substance is immiscible with water?
a.
2-butanol
c.
ethanal
b.
2-methyl-3-heptene
d.
methanoic acid
In which of the following solvents would candle wax, C25H52, dissolve in the best?
a.
H2O
c.
C9H18
b.
CH3OH
d. C3H7OH
In which of the following compounds is hexane most likely to dissolve?
19
Organic Chemistry Testbank
a.
b.
acetic acid
decane
c.
d.
20
ethyl alcohol
water
nonane
Boiling Points
Which substance would have the highest boiling point?
a.
C7H12
c.
C14H28
b.
C9H16
d.
C22H40
Which of the following compounds has the lowest boiling point?
a.
heptane
c.
2,3-dimethylpentane
b.
2-methylhexane
d.
2,2,3-trimethylbutane
Which substance would have the lowest boiling point?
a.
C7H12
c.
C14H28
b.
C9H16
d.
C22H40
Which alkene has the highest boiling point at atmospheric pressure?
a.
C2H4
c.
C4H8
b.
C3H6
d.
C5H10
What is the main force that influences boiling points in pure hydrocarbons?
a.
covalent bonding
c.
hydrogen bonding
b.
dipole-dipole attractions
d.
London Dispersion Forces
Which property is generally accepted as an indicator of the strength of intermolecular forces
within a substance?
a.
boiling point
c.
isomerism
b.
London dispersion force
d.
solubility
Alkanes, alkenes, and alkynes with the same number of carbons have:
a.
similar boiling and melting points primarily because they have nearly the same
molecular weight
b.
similar boiling and melting points primarily because they have similar polarities
c.
similar boiling and melting points primarily because they are nearly equal in
stability
d.
vastly different boiling and melting points
If alkenes of four carbons or less exist as gases at room temperature, how many alkenes exist as
gases under these conditions?
a.
2
c.
4
b.
3
d.
5
What is the physical state of the smallest alkanes (C1-C4) at room temperature?
a.
gas
c.
solid
b.
liquid
d.
gas or liquid
Intermolecular Forces
In which substance would London dispersion forces be the only intermolecular force of
attraction?
a.
1-pentanol
c.
pentanal
Organic Chemistry Testbank
21
b.
pentanoic acid
d.
pentyne
Which substance would be able to form hydrogen bonds to water but would not have any
hydrogen bonding between their own molecules?
a.
ethanol
c.
propanal
b.
propanoic acid
d.
propanol
Hydrogen bonding is most noticeable in
a.
alkanes
c.
esters
b.
alkynes
d.
organic acids
Why is a carbon-hydrogen bond essentially nonpolar?
a.
Neither atom is ionic.
b.
Free electrons cancel any polarity.
c.
The electron pair is shared almost equally.
d.
Van der Waals forces overcome polarity.
Lewis Dot Diagrams/Carbon Bonding
How many valence electrons surround a carbon atom?
a.
1
c.
3
b.
2
d.
4
How many covalent bonds does each carbon atom participate in an organic compound?
a.
1
c.
3
b.
2
d.
4
Which is the correct Lewis Dot diagram for acetylene, C2H2?
a.
c.
HC
CH
H C C H
c.
d.
HC
CH
H C C H
Benzene Bonding
What compound is the simplest of the arenes?
a.
benzene
c.
ethyne
b.
ethene
d.
methane
Which of the following molecules does NOT have delocalized electrons?
a.
benzene
c.
cyclohexane
b.
2-phenylpentane
d.
toluene
The compound benzene puzzled chemists for many years. Empirical research indicates that
carbon-carbon bonds in benzene are
a.
all carbon-carbon single bonds
b.
all carbon-carbon double bonds
c.
neither double nor single bonds
Organic Chemistry Testbank
22
d.
easily broken in chemical reactions.
Which chemical has delocalized electrons?
CH2
H3C
a.
H3C
C
CH
b.
CH3
c.
d.
What distinguishes benzene and benzene compounds from other organic compounds?
a.
benzene and benzene compounds are planar molecules
b.
carbon atoms in benzene have 120 bond angles
c.
carbon atoms in the benzene ring have just three bonding electrons
d.
carbon-carbon bonds in benzene involve delocalized bonding electrons
Functional Groups/hydrocarbon derivatives
Which of the following is a hydrocarbon derivative?
a.
C3H8
c.
C9H18
b.
CH4
d.
C3H70H
An arrangement of several atoms which gives characteristic properties to an organic molecule is
known as a(an)
a.
carboxyl group
c.
group
b.
functional group
d.
alkyl group
What is primarily responsible for the chemical properties of a hydrocarbon derivative like
ethanol?
a.
its delocalized electrons
c.
its functional group
b.
its level of saturation
d.
its solubility in water
In the general formula for alcohols, R-OH, the "R' represents
a.
radon
c.
the functional group
b.
CH3 only
d.
an alkyl group
The functional group for aldehydes is:
a.
hydroxyl
c.
carboxyl
b.
carbonyl
d.
ester
The functional group for ketones is:
c.
hydroxyl
c.
carboxyl
d.
carbonyl
d.
ester
The functional group for alcohols is:
e.
hydroxyl
c.
carboxyl
f.
carbonyl
d.
ester
The functional group for carboxylic acids is:
Organic Chemistry Testbank
23
g.
hydroxyl
c.
carboxyl
h.
carbonyl
d.
ester
Which compound contains the functional group called hydroxyl?
a.
CH3OH
c.
HCOOH
b.
H2CO
d.
NH4CH3COO
The functional group for alcohols is
a.
hydroxyl
c.
carboxyl
b.
carbonyl
d.
ester
Organic Reactions
Complete the following reactions by identifying reaction type, predicting products where
necessary, drawing structures for ALL organic reactants and products and naming ALL
products. Indicate if more than two products are possible.
Respiration/Photosynthesis:
Which biological process produces glucose from carbon dioxide and water?
a.
carbonization
c.
fusion
b.
photosynthesis
d.
respiration
Cracking/Reforming
Which reaction type uses ethene and low molecular weight hydrocarbons and converts them into
gasoline grade hydrocarbons?
a.
cracking
c.
esterification
b.
elimination
d.
reforming
What is the name of the process in which large molecules are broken down into smaller
molecules in order to increase the yield of gasoline from petroleum?
a.
polymerization
c.
esterification
b.
hydrogenation
d.
cracking
Which chemical reaction may be used to convert straight-chain aliphatic hydrocarbons to
alkylated or branched hydrocarbons?
a.
elimination
c.
esterification
b.
reforming
d.
substitution
n-decane + H2  butane + _______
+
H2
Substitution
Which is NOT a possible product in the reaction between benzene and 2 mol of bromine?
Organic Chemistry Testbank
a.
1,3-dibromobenzene
c.
1,2,3,4-tetrabromobenzene
b.
o-dibromobenzene
d.
hydrogen bromide
Which is NOT a possible product in the reaction between benzene and 2 mol of chlorine?
a.
1,2-dichlorobenzene
c.
1,2,4,5-tetrachlorobenzene
b.
p-dichlorobenzene
d.
hydrogen chloride
Which pairs of reactants are most likely to react by a substitution reaction?
I.
H2
II.
Cl2
III.
C2H4 IV.
C2H6
a.
I and III
c.
I and IV
b.
II and III
d.
II and IV
Which pairs of reactants are most likely to react by a substitution reaction?
I.
Br2
II.
HBr III.
C2H6 IV.
C2H4
a.
I and III
c.
I and IV
b.
II and III
d.
II and IV
Which type of compound will undergo a substitution reaction with a halogen?
a.
an alkane
c.
an alkyne
b.
an alkene
d.
a ketone
Based on the generalizations for reaction types, butane and fluorine gases react by
a.
addition
c.
combustion
b.
esterification
d.
substitution
Short answer:
propane + 1 mol chlorine
pentane + 1 mol bromine
benzene + 2 mol bromine
m-dimethylbenzene + chlorine
butane + 2 mol bromine
pentane + Br2
hexane
+
chlorine
Addition
Which IS a product of the reaction between 2-butene and 1 mol of chlorine?
a.
1,2-dichlorobutane
c.
1,3-dichlorobutane
b.
2,3-dichlorobutane
d.
1-4-dichlorobutane
Which IS a product of the reaction between propene and 1 mol of chlorine?
a.
1,2-dichloropropane
c.
hydrogen
b.
1,3-dichloropropane
d.
1-chloropropane
Which is NOT a product of the reaction between 1-pentyne and 2 mol of hydrogen bromide?
a.
1,1-dichloropentane
c.
1,3-dichloropentane
b.
1,2-dichloropentane
d.
2,2-dichloropentane
What type of reaction is
C2H4+ H2 C2H6
?
24
Organic Chemistry Testbank
25
a.
addition
c.
condensation
b.
substitution
d.
esterification
Which equation represents an addition reaction?
a.
CH3CH3 + Cl2 CH3CH2Cl + HCl
b.
CH2CH2 + Cl2 CH2ClCH2Cl
c.
CH3CH2Cl + OHB  CH2CH2 + H2O + ClB
d.
CH2CH2 + CH3CH3 (CH3)2CHCH3
How many products will result when 1-butene reacts with water?
a.
1
c.
3
b.
2
d.
4
How many products will result when 2-butene reacts with water?
a.
1
c.
3
b.
2
d.
4
Which organic reactant will produce 3-chloropentane when reacted with hydrogen chloride?
a.
pentane
c.
2-pentene
b.
1-pentene
d.
2-pentyne
Short answer
2-pentyne + excess HCl
2-pentyne + 2 mol HCl
2-butyne + 2 mol HBr
1-butyne + 2 mol HCl
3-octene + hydrogen iodide
1-pentene + water
1-butene + water
3-heptene + water
4-methyl-1-butyne + 1 mol hydrogen
Esterfication
Which of the following pairs of compounds could be combined to synthesize the compound
responsible for the odor of pears, pentyl ethanoate?
a.
1-pentanol and ethanol
c.
1-pentanol and ethanoic acid
b.
ethanal and pentanoic acid
d.
ethanol and 1-pentene
Which substance would be the best choice as a catalyst for a reaction between octanoic acid and
ethanol?
a.
acetic acid
c.
methanol
b.
sodium hydroxide
d.
sulfuric acid
What is the organic product of the reaction of methanol and ethanoic acid?
a.
propanone
c.
ethyl methanoate
b.
propanal
d.
methyl ethanoate
Short answer
ethanoic acid + 1-pentanol
Organic Chemistry Testbank
propanol + butanoic acid
methanoic acid + 1-pentanol
1-butanol
+
_________________

26
butyl propanoate
Hydrocarbon Combustion
When hydrocarbons are burned completely, which product is always formed?
a.
amorphous graphite
c.
limewater
b.
carbon dioxide
d.
methane
Short answer
2-methyl-1-butene + oxygen (Balance this reaction)
2-methyl-1-hexene + oxygen (Balance this reaction)
3-methyl-1-pentyne + oxygen
3,4-diethyl-2-pentene + oxygen
Elimination
Which substance will undergo an elimination reaction when reacting with hydroxide ions?
a.
2-fluoropropane
c.
ethanoic acid
b.
methyl methanoate
d.
propanal
Which compound, when heated in the presence of a strong acid, will produce a second compound
that will react quickly with bromine, even in the dark?
a.
acetylene
c.
1-hexanol
b.
2-butene
d.
pentane
Which reaction will not produce an alkene?
a.
2-chlorohexane is heated with sodium hydroxide
b.
2-pentyne and hydrogen are mixed in the presence of a platinum catalyst
c.
1-propanol is warmed with butanoic acid in the presence of a strong acid
d.
3-propanol is warmed in the presence of a strong acid
Short answer
2-chlorobutane + hydroxide ions
2-chlorobutane
+
sodium hydroxide
2-pentanol is warmed in the presence of a strong acid
2
4
ethanol   
H SO
2
4
 

H SO
3-heptanol
Reaction type: _______________________
Identifying Polymerization
Organic Chemistry Testbank
27
Identify the reaction type:
O
n
C
+
C
HO
a.
b.
O
O
OH
C
n CH2 CH2
HO
O
C
O
OH
addition polymerization
esterification
c.
d.
CH2
O
CH2
+
n
condesation polymerization
hydrocarbon combustion
Identify the reaction type:
H
H
C
n
C
H
a.
b.
CH3
H
H
C
C
H
CH3
addition polymerization
esterification
n
c.
d.
condesation polymerization
hydrocarbon combustion
What monomer was used to produce the polymer:
CH3
CH3
CH3
...
...
H3C
CH3
C
a.
H3C
C
H
H
C
H
b.
C
H
H
CH3
H3C
CH3
C
c.
H
H3C
C
CH3
C
C
CH3
d.
H
H
n H2O
Organic Chemistry Testbank
28
Condensation Polymerization
Which polymer was produced by condensation polymerization?
CH3
CH3
O
O
O
O
n
a.
CH3
CH3
CH3
CH3
....
b.
CH3
....
CH3
CH
CH
CH3 H
C
n
c.
C
CH3 H
d.
n
Long answer:
Proteins are the building blocks of the human body. They are composed of chains of amino
acids, and make up our skin, nails, hair and connective tissue. The type of protein formed
depends upon the sequence of the amino acids in the chain.
Some amino acids are given below.
CH3
O
alanine
NH2
NH2
glycine
O
Organic Chemistry Testbank
O
a.
b.
c.
SH
NH2
NH2
cysteine
29
O
Threonine
What type of reaction will link these amino acids into a long chained protein?
What are the chemical characteristics of these molecules that allow them to form
long chains? Pick one of the amino acids to illustrate your answer.
The protein in hair will curl around in a helix shape, held together by hydrogen
bonds. Draw a dotted line to show where hydrogen bonding could occur if
cysteine and threonine were close together on two different protein chains. (2)
O
SH
NH2
cysteine
NH2
O
OH
threonine
CH3
Addition Polymerization
Which substance will undergo addition polymerization?
a.
1-propanol
c.
propanal
b.
propanone
d.
propene
Which monomer will produce the polymer on the right?
a.
1-pentene
b.
2-pentene
c.
ethylmethylethane
d.
pentane
H
H
C
C
CH3 CH2
CH3
Which synthetic polymer is the product of addition polymerization?
a.
cellulose
c.
ribonucleic acid (RNA)
b.
protein
d.
teflon
Short answer
addition polymerization reaction with 1-pentene
addition polymerization reaction with 1-butene
n
Organic Chemistry Testbank
n
30
2-pentyne
Long Answer Questions:
When ethene reacts with chlorine in the absence of light, only one product forms. However, if
ethene reacts with chlorine in the presence of light, over a long period of time, many products are
formed.
a.
Identify the reaction type when ethene reacts in the absence of light, and write
equation to show the product formed. Name and draw the product. (4%)
b.
Identify the two reaction types when ethene reacts in the presence of light, and
write an equation to illustrate each. Name and draw all possible products. (8%)