Organic Chemistry Testbank 1

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 Kekul c. Friedrich Whler
b. !ohn "alton d. #aymond $e%ieu&
The A'italism@ theory in organic chemistry held that
a. organic chemicals can only be obtained from li'ing organisms
b. organic chemicals can only be obtained from dead organisms
c. organic chemicals can only be obtained from li'ing or dead organisms
d. organic chemicals can be obtained from any source of chemicals( organic or
inorganic.
Long Answer:
)&plain why Whlers synthesis of urea by heating ammonium cyanate crystals was a landmark
e'ent in the study of organic compounds.
Definition of Organic Chemistry
*rganic chemicals
a. are all the compounds of carbon including the ionic compounds
b. are all the molecular compounds of carbon e&cept the o&ides
c. are all the ionic compounds of carbon including the o&ides
d. can only be made by li'ing organisms
Throughout history there ha'e 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+li'ing substances only
d. substances deri'ed from li'ing things.
Which is an organic chemical,
a. -a-*. c. -l/
b. --l0 d. -*/
Which is NOT an organic chemical,
a. -1.-**1 c. -012*
b. -*/ d. --l0
Which is NOT an organic chemical,
c. -1.-1* c. -/13*
d. -4r0 d. -*
Which substance is organic,
a. Ag-l c. 510-5
b. Ag*-5 d. 651/7/-*
Multitude of Organic Chemicals
Which statement is true,
a. -arbon can bond in chains with branches( but cannot form rings
b. -arbon can form single bonds( but not double and triple bonds.
Organic Chemistry Testbank /
c. -arbon can bond in chains with branches( in rings( and with single( double and
triple bonds
d. -arbon cannot form rings with double bonds or branches on them
Which statement is true,
a. *'er 89: of all known compounds are organic
b. *'er 89: of all known compounds are inorganic
c. There are about / times as many inorganic compounds as organic compounds
d. There are about / 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 belie'ed to be due( in large part( to the
a. high bonding capacity of a carbon atom.
b. ability of carbon atoms to form co'alent bonds with hydrogen.
c. high number of lone pairs of electrons of a carbon atom.
d. large 'ariety of chemical reactions of elemental carbon
hort Answer;
$ist three factors that contribute to the tremendous di'ersity of carbon compounds relati'e to the
number of inorganic compounds.
<i'e two 6good7 reasons why carbon has its own branch of chemistry.
Homologous eries
)ach member of the alkane series differs from the preceding member by one additional carbon
atom and
a. 1 hydrogen atom c. / hydrogen atoms
b. . hydrogen atoms d. 0 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 ha'e more isomers as they get larger
c. has a boiling point that increases as they get larger
d. increases by A+-1/= as they get larger
Which of the following is part of a homologous series;
a. -10( -/10( -01> b. -10( -/1/( -.13
c. -.1>( -.13( -.10 d. -/10( -.13( -01>
Which term describes this group of compounds,
chloromethane( chloroethane( 1+chloropropane( 1+chlorobutane
a. aldehydes c. functional isomers
b. aromatics d. homologous series
Alkanes!traight chain alkanes
Alkanes 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 co'alent bonds
1ow many double co'alent bonds are in an alkane,
a. none c. one
Organic Chemistry Testbank .
b. two d. The number 'aries
1ow many carbons are in a molecule of he&ane,
a. . b. 0
b. ? d. 3
What is the name of the alkane ha'ing fi'e carbons,
a. he&ane c. methane
b. octane d. pentane
What increment of change occurs between propane and butane in the alkane series,
4
a. +-1+ b. +-1/+
b. +-1.+ d. +-1/@
Which of the following is a condensed structural diagram for propane,
a. -.1>
b. -1.+-1/+-1. d.
c. -+-+-
What is the name of the molecule on the right,
a. butane
b. pentane
c. propane
d. tetrane
What is the name of the molecule on the right,
a. butane
b. pentane
c. propane
d. he&ane
What is the ABCA- name of the compound on the right,
a. butane
b. decane
c. propane
d. pentane
What is the name of the straight chain alkane with 2 carbons,
a. pentane c. he&ene
b. heptane d. octyne
"ranched Alkanes + Nomenclature
Which condensed structural formula represents the alkyl group called ethyl,
a. -1-1 c. -1/-1.
b. -1/-1/ d. -1.-1.
What is the name of an alkyl group that contains two carbon atoms,
a. diphenyl c. dimethyl
b. ethyl d. propyl
What prefi& is used to represent the substituent -1.+-1/+-1/+,
a. ethyl+ c. methyl+
b. propyl+ d. pentyl
Af a substituent appears four times in an organic compound( what prefi& is used,
a. di+ c. mono+
C C C C C
H
H
H
H
H H
H H
H
H
H
H
C C C
H
H
H H
H H
H
H
C H
3
CH
2
CH
2
CH
3
C H
3
CH
2
CH
2
CH
2
CH
2
CH
3
Organic Chemistry Testbank 0
b. penta+ d. tetra+
What is the name of the compound on the right,
a. /(0+diethyl+/+methylhe&ane
b. .+ethyl+?(?+dimethylheptane
c. ?+ethyl+.(.+dimethylheptane
d. .(?+diethyl+?+methylhe&ane
What is the ABCA- name of compound on the right,
a. /+ethyl+.+dimethylhe&ane
b. /+ethyl+.(.+diemethylhe&ane
c. 0(0(?+trimethylheptane
d. .(0(0+trimethylheptane
What is the ABCA- name of compound on the right,
a. /(.+dimethylpentane
b. .(0+dimethylpentane
c. .(0(0 +trimethylbutane
d. /(.(0+trimethylbutane
What is the ABCA- name of compound on the right,
a. trimethylpentane
b. /+methyl+.+methyl+0+methylpentane
c. /(/+dimethyl+.+methylpentane
d. /(.(0+trimethylpentane
What is the ABCA- name of compound on the right,
a. /+ethyl+/(0(?+trimethylpentane
b. /+ethyl+/(0+dimethylhe&ane
c. .(?(?+trimethylheptane
d. .(.(?+trimethylheptane
What is the correct ABCA- name for the compound shown below,
-1..-16-1/.-1.7.-16-1.7/
a. /(.+dimethyl pentane c. 1(1(/+trimethyl butane
b. /+ethyl+.+methyl butane d. .(0+dimethyl pentane
Which is the condensed structural formula for /(/(.+trimethylbutane,
a. -1.-1/6-1.7-16-1.7/ c. -1.-6-1.7/-6-1.7.
b. -1.-6-1.7/-16-1.7/ d. -1.-1/-16-1.7-6-1.7.
What is the ABCA- name for this compound, -1.-16-1.7-6-1.7..
a. /(/(.+trimethylbutane c. tetramethylpropane
b. 1(1(1(/+tetramethylpropane d. heptane
CH
2
CH
3
CH
2
CH
2
C CH
3
CH
2
CH
3
CH
3
C H
3
CH
CH CH
CH
3
CH
3
C H
3
CH
3
C C
C C
C
C
H
H
H
H
H
H
H H
H
H H
H
CH
3
C H CH CH
2
CH
2
CH
3
C H
3
CH
2
C C
CH
2
CH
3
CH
3
H
Organic Chemistry Testbank ?
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 co'alent bonds
Which hydrocarbon contains a double carbon to carbon bond,
a. 1+butene c. /+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,
a. /+ethyl+.+propyl+1+pentene
b. /(.+diethyl+0+methyl+1+pentene
c. .+ethyl+/(0+dimethyl0+he&ene
d. .(0+diethyl+/+methyl+0+pentene
What is the name of the molecule on the right,
a. /(.+dimethyl+0+propyl+0+pentene
b. /(.+dipropyl+1+butene
c. .(0+dimethyl+/+propyl+1+pentene
d. 0(?(3+trimethyl+0+heptene
What is the ABCA- name of this compound,
a. 1(1+dimethyl+/+butene
b. /+methyl+.+pentene
c. 0+methyl+/+pentene
d. methylhe&ane
According to the rules established by chemists( what is the ABCA- name of the
compound on the right,
a. 1+methyl+1+pentene
b. ?+methyl+0+pentene
c. /(.+he&ene
d. /+he&ene.
"etermine the ABCA- name for the following molecule;
a. /(?+dimethyl+/+he&ene
b. /(?+dimethyl+0+he&ene
c. /(?+dimethyl+/+heptene
d. /(?+dimethyl+0+heptene
What is the name for the following molecule,
a. /+ethyl+/+pentene
b. 0+ethyl+.+pentene
c. .+methyl+.+he&ene
CH
2
C CH
CH
2
CH
2
CH CH
3
CH
3
CH
3
CH
3
CH
2
C CH
CH
2
CH
3
CH CH
3
CH
3
CH
2
CH
3
Organic Chemistry Testbank 3
d. 0+methyl+.+he&ene
The correct name for the compound 6-1.7/-1.-16-1.7.-1/.-1;-1/ is;
a. 0(?(?+trimethyl+1+pentene b. 0(?+dimethyl+1+he&ene
c. /(.+dimethyl+?+he&ene d. 0+propyl+0+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 co'alent bonds
What is the name of the smallest alkyne,
a. butyne c. ethyne
b. methyne d. propyne
What is the name of the molecule on the right,
a. 0(0+diethyl+/+butyne
b. 0+ethyl+/+he&yne
c. .+ethyl+0+he&yne
d. 1(1+diethyl+/+butyne
What is the name of the molecule on the right,
a. 1(3(3(3+tetramethyl+/+pentyne
b. /(/+dimethyl+0+heptyne
c. /(/(3+trimethyl+0+he&yne
d. 3(3+dimethyl+.+heptyne
Which is the condensed structural diagram for 0+methyl+/+
pentyne,
a.
C H
C
CH
2
CH
CH
3
CH
3
c.
C H
3
CH C C CH
3
C H
3
b.
C H
3
CH
CH
CH
CH
3
CH
3
d.
C H
2
CH
CH
2
CH
CH
3
CH
3
What is the name of the molecule
C H
3
C CH
,
a. acetylene c. propyne
b. 1+butyne d. propene
Cycloalkanes$ cylcoalkene # Nomenclature
What is the name of the molecule on the right,
a. ethylbenzene
CH
2
C C CH
2
CH
3
C C H
3
CH
3
C H
3
C H
3
C C C H
CH
2
CH
3
CH
2
CH
3
CH
3
Organic Chemistry Testbank 2
b. ethylcyclohe&ane
c. phenylethane
d. propylcyclohe&ane
What is the name of the molecule on the right,
a. butylcyclohe&ane
b. phenylpropane
c. propylbenzene
d. propylcyclohe&ane
What is the name of the molecule on the right,
a. ethylcyclopentane
b. pentylcyclopropane
c. propylcylclopentane
d. propylcyclohe&ane
What is the name of the molecule on the right,
a. /+ethylcyclopentene
b. .+ethylcyclopentene
c. /+ethyl+/+cyclopentene
d. ?+ethyl+/+cyclopentene
What is the name of the molecule on the right,
a. /+methylcyclohe&ene
b. .+methylcyclohe&ene
c. 0+methylcyclohe&ene
d. ?+methylcyclohe&ene
Delect the proper order of stability from least to most stable for the following cycloalkenes;
A
B C
a. A( 4( - c. -( A( 4
b. 4( -( A d. -( 4( A
im%le Aromatics # nomenclature
What is the name of the molecule on the right,
a. /+butylbenzene
b. butylbenzene
c. phenylbutane
d. propylbenzene
What is the name of the molecule on the right,
a. butylbenzene
b. /+pentylbenzene
CH
2
CH
2
CH
2
CH
3
CH
2
CH
2
CH
2
CH
2
CH
3
Organic Chemistry Testbank >
c. pentylbenzene
d. phenylpentane
What is the ABCA- name of the compound on the right,
a. pentylcyclohe&ane
b. cyclopentylhe&ane
c. pentylbenzene
d. he&ylbenzene
What is the ABCA- name of the compound on the right,
a. butylbenzene
b. phenylbutane
c. propylbenzene
d. phenylpropane
&henyl "ranches # nomenclature
What is the ABCA- name of the molecule on the right,
a. 1(1(0+trimethyl+0+phenylbutane
b. /(0+dimethyl+?+phenylpentane
c. /(0+dimethyl+/+pentylbenzene
d. /(0+dimethyl+1+phenylpentane
What is the ABCA- name of the molecule on the right,
a. /+methyl+.+ethyl+1+phenylbutane
b. /(.+dimethyl+1+phenylpentane
c. /(.+dimethyl+1+pentylbenzene
d. .(0+dimethyl+?+phenylpentane
What is the ABCA- name for the molecule on the right,
a. /+pentylbenzene
b. /+phenypentane
c. 1 +methyl+1+phenylbutane
d. pentylbenzene
1ow many phenyl groups does the following molecule ha'e,
a. 9
c. /
b. 1
d. 3
Disubstituted ben'enes
What is another acceptable name for 1(.+dimethylbenzene,
a. m+dimethylbenzene c. o+dimethylbenzene
b. n+dimethylbenzene d. p+dimethylbenzene
What is another acceptable name for 1(0+dimethylbenzene,
a. m+dimethylbenzene c. o+dimethylbenzene
b. n+dimethylbenzene d. p+dimethylbenzene
What is another acceptable name for 1(/+dimethylbenzene,
a. m+dimethylbenzene c. o+dimethylbenzene
b. n+dimethylbenzene d. p+dimethylbenzene
CH
2
CH
CH
2
CH
CH
3
CH
3
CH
3
CH
2
CH
CH
3
CH
C H
3
CH
2
CH
3
C H
CH
2
CH
2
CH
3
CH
3
Cl Cl
Organic Chemistry Testbank 8
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
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 ABCA- name for the isomeric compound on the right,
a. 1(/+dichlorobenzene
b. 1(.+dichlorobenzene
c. /(/+dichlorobenzene
d. /(3+dichlorobenzene
Which of the following molecules is p+ethylmethylbenzene,
a. b.
c. d.
(nits of (nsaturation!general formulas
What type of hydrocarbon is the compound on the right, -1.+-1/+-1/+-1/+-1/+-1.
a. aliphatic c. cyclic
b. aromatic d. unsaturated
Which hydrocarbon is saturated,
a. -313 c. -311/
b. -3119 d. -3110
Which is the formula of a saturated hydrocarbon,
a. -/1/ c. -/10
b. -?1> d. -?11/
Which is the formula of a saturated hydrocarbon,
CH
3
C H
3
Organic Chemistry Testbank 19
a. -1/-1/ c. -313
b. -1.-1-1/ d. 6-1.7.-1
A saturated continuous+chain hydrocarbon with se'en carbons is EEEEE.
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
1ow many units of unsaturation does the molecular formula -?1> ha'e,
a. none c. two
b. one d. three
1ow many units of unsaturation does the molecular formula -211/ ha'e,
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. -?119 c. -?1>
b. -3110 d. -311/
Which could be a molecular formula for an organic chemical with one ring,
a. -?119 c. -?1>
b. -3110 d. -3119
Which could be a molecular formula for a non+cyclic hydrocarbon with two double bonds,
a. -?119 c. -?1>
b. -3110 d. -311/
What is the molecular formula for .(.+diethyl+0+methyl+1+he&yne,
a. -1911> c. -111//
b. -111/9 d. -1/1//
Which formula represents a member of the alkene series,
a. -.13 c. -/1/
b. -/13 d. -313
Which formula represents a member of the alkane family,
a. -.13 c. -/1/
b. -/13 d. -313
What is the general formula for a continuous+chain alkane,
a. -n1n c. -n1/n+/
b. -n1nF/ d. -n1/nF/
To which class of aliphatic hydrocarbons does -/?1?/ belong,
a. alkanes c. alkynes
b. alkenes d. aromatics
Which of the following molecules is a saturated hydrocarbon,
a. b.
Organic Chemistry Testbank 11
c. d.
)somers:
Which molecule is NOT an isomer of -01>,
a. c.
b. d.
Which molecule is NOT an isomer of -?11/,
a. c.
b. d.
->113 could ha'e 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 /+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. /+methylbutane c. /(/+dimethylbutane
b. /+methylpropane d. /(/+diethylpropane
Which pairs of molecules are structural isomers,
a. cyclohe&ane and /(/+dimethylbutane
b. cyclohe&ene and .(.+dimethyl+1+butyne
c. methylcyclobutane and /+pentyne
Organic Chemistry Testbank 1/
d. /+methylpentyne and /+methylpentene
A structural isomer of he&ane is EEEEE.
a. benzene c. cyclohe&ane
b. /(/+dimethylbutane d. /+methylpentene
Which compound can ha'e isomers,
a. -/10 c. -/1/
b. -/13 d. -01>
1ow many structural isomers e&ist for the alkene -1/4r/,
a. 1 c. .
b. b. / d. 0
Which compound is an isomer of -1..-1/.-1/.-1/.*1
a. -1.-1/*-1. c. -1.-1/-1/-1.
b. -1.-1/-1/*1 d. -1.-16*17-1/-1.
Which of the following pairs of compounds are isomers,
a. diethyl ether and 1+butanol b. /+pentanone and /+pentanol
c. pentanal and methyl butanoate d. propanoic acid and propanal
Dtructural isomers ha'e EEEEE.
a. the same molecular formula
b. different physical and chemical properties
c. the same elemental composition
d. all of the abo'e
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
)somer # hort Answer
1a7 A student is told to draw the structural diagram of the compound with formula -0119 .
-onfused( the student tells the nai'e chemistry+challenged person that the task is impossible.
a7 Why can=t the student show the structure of -0119, 6/7
b7 #ephrase the Guestion by changing one word so that the Guestion can be answered( and
then answer it. 6Keep the fla'or of the Guestion + donHt change it completelyI7 607
1a7 <i'e a brief e&planation( using two e&amples( as to why the numbers are necessary for
identifying an organic compound sometimes( but not other times. 607
b7 Adentify which of the following names need numbers in front to identify them completely;
butanol( propanal( pentanone( he&ene( butanoic acid( methylpentane.6.7
1ow many different answers should you get to the Guestion( =What is the boiling point of
-.1>*,= )&plain with the use of structural diagrams( names and a brief discussion of
intermolecular attractions.
"raw structural formulas for and name four isomers of -012-l.
Halocarbons
Which substituent would allow a compound to be classified as an alkyl halide,
C H
3
C
CH
2
CH
CH
2
F
F
F
Br
Organic Chemistry Testbank 1.
a. fluorine c. o&ygen
b. nitrogen d. sulfur
The ABCA- name for the compound 6-1.7/-6-1/.-1.7.-1/.-1-l.-1. is;
a. ?+chloro+.(.+dimethylhe&ane c. /+chloro+0+methyl+0+ethylpentane
b. 0+chloro+/+ethyl+/+methylpentane d. 1+chloro+1(.(.(.+trimethylpentane
What is the name of the molecule on the right,
a. /+dichloro+.+methylpentane
b. /(/+dichloro+.+methylpentane
c. 0(0+dichloro+.+methylpentane
d. 0(0+dichloro+.(?+dimethylbutane
What is the name of the molecule on the right,
a. /(.+dichloro+/+methylpentane
b. 1(/+dichloro+1(1+dimethylbutane
c. /(.+chloro+/+methylpentane
d. .(0+dichloro+0+methylpentane
The correct name for the molecule on the right is;
a. 1(0(0+trifluoro+/+bromopentane
b. /+bromo+1(0(0+trifluoropentane
c. /(/(?+trifluoro+0+bromopentane
d. 0+bromo+/(/(?+trifluoropentane
Alcohols
What is the name of the molecule on the right,
a. butanone
b. /+butanol
c. /+butanal
d. butyl ether
What is the name of the molecule on the right,
a. .+pentanone
b. .+pentanal
c. .+pentanol
d. pentanoic acid
What is the correct ABCA- name for the compound shown below,
-1..-1/.-16-1/.-1.7.-16*17.-1.
a. .+ethyl+0+pentanol
b. /+methyl+?+he&anol
c. .+ethyl+/+pentanol
d. .+ethyl+/+heptanol
The correct ABCA- name for the compound -1..-1/.-1/.-6-1.7/.*1 is
a. 1+he&anol c. 1+ dimethylbutanol
b. 1(1+dimethyl+1+butanol d. /+methyl+/+pentanol
*thers
Which molecule is an ether,
CH
3
C CH CH
2
CH
3
Cl CH
3
Cl
C H
3
CH
2
CH
CH
2
OH
CH
3
C H
3
CH
2
CH CH
3
O H
CH
3
C CH CH
2
CH
3
Cl Cl
CH
3
Organic Chemistry Testbank 10
a+
C H
3
CH
CH
2
CH
2
CH
3
OH
c.
C H
3
C
O
CH
2
CH
3
O
b+
C H
3
CH
O
CH
2
CH
3
CH
3
d.
CH
2
C
OH
O CH
3
Which of the following is an ether,
a.
CH
3
CH
2
CH
2
CH
2
C
OH
O
c.
CH
3
CH
2
O CH
3
b.
CH
3
CH
2
CH
2
C
CH
3
O
d.
CH
3
CH
2
CH
2
CH
O
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,
a. pentanal
b. ethylpropyl ether
c. pentanone
d. ethyl propanoate
Aldehydes
Which molecule is an aldehyde,
a+
O
C
CH
2
CH
2
CH
3
CH
3
c.
C H
3
C
O
CH
2
CH
3
O
b+
C H
3
CH
O
CH
2
CH
3
CH
3
d.
H
C
CH
2
CH
2
CH
3
O
CH
3
O
CH
2
CH
2
CH
3
CH
2
O
CH
2
CH
2
CH
3
C H
3
Organic Chemistry Testbank 1?
Which of the following is an aldehyde,
a.
CH
3
CH
2
CH
2
CH
2
C
OH
O
c.
CH
3
CH
2
O CH
3
b.
CH
3
CH
2
CH
2
C
CH
3
O
d.
CH
3
CH
2
CH
2
CH
O
What is the ABCA- name of the molecule on the right,
a. butanal
b. 1+butanone
c. butanoic acid
d. propanal
What is the ABCA- 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. ethane
b. ethanol d. pentanal
Which of the following is an aldehyde,
a. butanal b. ethanone
c. ethanol d. pentanoic acid
,etones
What is the ABCA- name of the molecule on the right,
a. ethylpropyl ether
b. .+he&anal
c. .+he&anone
d. methyl butanoate
What is the ABCA- name of the molecule on the right,
a. diethyl ether
b. /+pentanone
c. .+pentanone
d. .+pentanal
Which of the following is a ketone,
a.
CH
3
CH
2
CH
2
CH
2
C
OH
O
c.
CH
3
CH
2
O CH
3
CH CH
2
CH
2
CH
3
O
CH CH
2
CH
2
CH
2
O
CH
3
O
O
CH
3
CH
2
O C
O
H
CH
2
CH
2
CH
2
C
OH
O
CH
3
O
O
Organic Chemistry Testbank 13
b.
CH
3
CH
2
CH
2
C
CH
3
O
d.
CH
3
CH
2
CH
2
CH
O
Which condensed structural formula represents a ketone,
a. -1.-1/-1/*1 c. -1.-*-1.
b. -1.-1/-1* d. -1.-1/-**1
Carbo-ylic Acids
What is the ABCA- name of the molecule on the right,
a. butanone
b. ethanoic acid
c. methy propanoate
d. propanoic acid
What is the ABCA- name of the molecule on the right,
a. butanal
b. butanoic acid
c. methy propanoate
d. propanoic acid
What is the ABCA- name of the molecule on the right,
a. pentanal
b. pentanoic acid
c. methy butanoate
d. pentanone
*sters
What is the ABCA- name of the molecule on the right,
a. butyl ethanoate
b. ethyl propanoate
c. ethyl butanoate
d. propyl ethanoate
What is the ABCA- name of the molecule on the right,
a. ethyl methanoate
b. methyl ethanoate
c. ethanoic acid
d. propanoic acid
What is the ABCA- name of the molecule on the right,
a. ethyl propanoate
b. methyl butanoate
c. butyl methanoate
d. methyl propanoate
Tri.ial Names
OH
O
O H
O
O
O
Organic Chemistry Testbank 12
What is the ABCA- name of the molecule on the right,
a. acetylene
b. formaldehyde
c. phenol
d. toluene
What is the ABCA- name of the molecule on the right,
a. acetylene
b. formaldehyde
c. phenol
d. toluene
/ractional Distillation!ources of hydrocarbons
Which molecule would condense closer to the top of a fractional distillation tower,
a. -?11/ c. -101.9
b. -191// d. -/910/
Which molecule would condense closer to the bottom of a fractional distillation tower,
a. -?11/ c. -101.9
b. -191// d. -/910/
Which is the correct statement regarding fractional distillation,
a. The mi&ture of hydrocarbons in crude oil are con'erted into the 'arious fractions
6gasoline( furnace oil( etc.7 by chemical reactions
b. Dubstances with high boiling points will condense lower in the fractional distillation
tower.
c. Fractions with 'ery low boiling points will condense before the fractions with high
boiling points
d. -rude 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 e'aporate relati'e 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 in'ol'es the con'ersion of once li'ing organic matter to fossil fuels,
a. carbonization c. combustion
CH
3
OH
Organic Chemistry Testbank 1>
b. nuclear fusion d.. photosynthesis
ha%es of molecules
The bonding shape around e'ery 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. cyclohe&ane
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
hort Answer:
1. 6a7 "raw $ewis diagrams for ethane and ethyne.
6b7 "escribe the shape around the carbon atoms in ethane 'ersus ethyne.
6c7 1ow does the shape and arrangement of bonding electrons influence the reacti'ity of
ethane 'ersus ethyne,
olubility
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. /+butanol c. ethanal
b. /+methyl+.+heptene d. methanoic acid
An which of the following sol'ents would candle wa&( -/?1?/( dissol'e in the best,
a. 1/* c. -811>
b. -1.*1 d. -.12*1
An which of the following compounds is he&ane most likely to dissol'e,
a. acetic acid c. ethyl alcohol
b. decane d. water
nonane
Organic Chemistry Testbank 18
"oiling &oints
Which substance would ha'e the highest boiling point,
a. -211/ c. -101/>
b. -8113 d. -//109
Which of the following compounds has the lowest boiling point,
a. heptane c. /(.+dimethylpentane
b. /+methylhe&ane d. /(/(.+trimethylbutane
Which substance would ha'e the lowest boiling point,
a. -211/ c. -101/>
b. -8113 d. -//109
Which alkene has the highest boiling point at atmospheric pressure,
a. -/10 c. -01>
b. -.13 d. -?119
What is the main force that influences boiling points in pure hydrocarbons,
a. co'alent bonding c. hydrogen bonding
b. dipole+dipole attractions d. $ondon "ispersion Forces
Which property is generally accepted as an indicator of the strength of intermolecular forces
within a substance,
a. boiling point c. isomerism
b. $ondon dispersion force d. solubility
Alkanes( alkenes( and alkynes with the same number of carbons ha'e;
a. similar boiling and melting points primarily because they ha'e nearly the same
molecular weight
b. similar boiling and melting points primarily because they ha'e similar polarities
c. similar boiling and melting points primarily because they are nearly eGual in
stability
d. 'astly different boiling and melting points
Af alkenes of four carbons or less e&ist as gases at room temperature( how many alkenes e&ist as
gases under these conditions,
a. / c. 0
b. . d. ?
What is the physical state of the smallest alkanes 6-1+-07 at room temperature,
a. gas c. solid
b. liGuid d. gas or liGuid
)ntermolecular /orces
An which substance would $ondon dispersion forces be the only intermolecular force of
attraction,
a. 1+pentanol c. pentanal
b. pentanoic acid d. pentyne
Which substance would be able to form hydrogen bonds to water but would not ha'e any
hydrogen bonding between their own molecules,
a. ethanol c. propanal
b. propanoic acid d. propanol
1ydrogen bonding is most noticeable in
Organic Chemistry Testbank /9
a. alkanes c. esters
b. alkynes d. organic acids
Why is a carbon+hydrogen bond essentially nonpolar,
a. 5either atom is ionic.
b. Free electrons cancel any polarity.
c. The electron pair is shared almost eGually.
d. Jan der Waals forces o'ercome polarity.
Lewis Dot Diagrams!Carbon "onding
1ow many 'alence electrons surround a carbon atom,
a. 1 c. .
b. / d. 0
1ow many co'alent bonds does each carbon atom participate in an organic compound,
a. 1 c. .
b. / d. 0
Which is the correct $ewis "ot diagram for acetylene( -/1/,
a.
C C H H
c.
C C H H
c.
C C H H
d.
C C H H
"en'ene "onding
What compound is the simplest of the arenes,
a. benzene c. ethyne
b. ethene d. methane
Which of the following molecules does 5*T ha'e delocalized electrons,
a. benzene c. cyclohe&ane
b. /+phenylpentane d. toluene
The compound benzene puzzled chemists for many years. )mpirical 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
d. easily broken in chemical reactions.
Which chemical has delocalized electrons,
a.
C H
3
C CH
b.
C H
3
CH
3
CH
2
Organic Chemistry Testbank /1
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 ha'e 1/9 bond angles
c. carbon atoms in the benzene ring ha'e Kust three bonding electrons
d. carbon+carbon bonds in benzene in'ol'e delocalized bonding electrons
/unctional 0rou%s!hydrocarbon deri.ati.es
Which of the following is a hydrocarbon deri'ati'e,
a. -.1> c. -811>
b. -10 d. -.1291
An arrangement of se'eral atoms which gi'es characteristic properties to an organic molecule is
known as a6an7
a. carbo&yl group c. group
b. functional group d. alkyl group
What is primarily responsible for the chemical properties of a hydrocarbon deri'ati'e like ethanol,
a. its delocalized electrons c. its functional group
b. its le'el of saturation d. its solubility in water
An the general formula for alcohols( #+*1( the =#H represents
a. radon c. the functional group
b. -1. only d. an alkyl group
The functional group for aldehydes is;
a. hydro&yl c. carbo&yl
b. carbonyl d. ester
The functional group for ketones is;
c. hydro&yl c. carbo&yl
d. carbonyl d. ester
The functional group for alcohols is;
e. hydro&yl c. carbo&yl
f. carbonyl d. ester
The functional group for carbo&ylic acids is;
g. hydro&yl c. carbo&yl
h. carbonyl d. ester
Which compound contains the functional group called hydro&yl,
a. -1.*1 c. 1-**1
b. 1/-* d. 510-1.-**
The functional group for alcohols is
a. hydro&yl c. carbo&yl
b. carbonyl d. ester
Organic Chemistry Testbank //
Organic 1eactions
-omplete the following reactions by identifying reaction type( predicting products where
necessary( drawing structures for ALL organic reactants and products and naming ALL products.
Andicate if more than two products are possible.
Respiration/Photosynthesis:
Which biological process produces glucose from carbon dio&ide and water,
a. carbonization c. fusion
b. photosynthesis d. respiration
Cracking/Reforming
Which reaction type uses ethene and low molecular weight hydrocarbons and con'erts 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 con'ert straight+chain aliphatic hydrocarbons to
alkylated or branched hydrocarbons,
a. elimination c. esterification
b. reforming d. substitution
n+decane F 1/ butane F EEEEEEE
Substitution
Which is NOT a possible product in the reaction between benzene and / mol of bromine,
a. 1(.+dibromobenzene c. 1(/(.(0+tetrabromobenzene
b. o-dibromobenzene d. hydrogen bromide
Which is NOT a possible product in the reaction between benzene and / mol of chlorine,
a. 1(/+dichlorobenzene c. 1(/(0(?+tetrachlorobenzene
b. p-dichlorobenzene d. hydrogen chloride
Which pairs of reactants are most likely to react by a substitution reaction,
A. 1/ AA. -l/ AAA.
-/10 AJ. -/13
a. A and AAA
+
H
2
Organic Chemistry Testbank /.
c.
A and
AJ
b. AA and AAA
d.
AA and
AJ
Which pairs of reactants are most likely to react by a substitution reaction,
A. 4r/ AA. 14r
AAA. -/13
AJ. -/10
a. A and AAA
c.
A and
AJ
b. AA and AAA
d.
AA and
AJ
Which type of compound will undergo a substitution reaction with a halogen,
a. an alkane c. an alkyne
b. an alkene d. a ketone
4ased on the generalizations for reaction types( butane and fluorine gases react by
a. addition c. combustion
b. esterification d. substitution
Short answer;
propane F 1 mol chlorine
pentane F 1 mol bromine
benzene F / mol bromine
m+dimethylbenzene F chlorine
butane F / mol bromine
pentane F 4r/
Organic Chemistry Testbank /0
he&ane F chlorine
Addition
Which ) a product of the reaction between /+butene and 1 mol of chlorine,
a. 1(/+dichlorobutane c. 1(.+dichlorobutane
b. /(.+dichlorobutane d. 1+0+dichlorobutane
Which ) a product of the reaction between propene and 1 mol of chlorine,
a. 1(/+dichloropropane c. hydrogen
b. 1(.+dichloropropane d. 1+chloropropane
Which is NOT a product of the reaction between 1+pentyne and / mol of hydrogen bromide,
a. 1(1+dichloropentane c. 1(.+dichloropentane
b. 1(/+dichloropentane d. /(/+dichloropentane
What type of reaction is -/10F 1/ -/13 ,
a. addition c. condensation
b. substitution d. esterification
Which eGuation represents an addition reaction,
a.
-1.-1. F -l/ -1.-1/-l F 1-l
b.
-1/-1/ F -l/ -1/-l-1/-l
c.
-1.-1/-l F *1
B
-1/-1/ F 1/* F -l
B
d.
-1/-1/ F -1.-1. 6-1.7/-1-1.
1ow many products will result when 1+butene reacts with water,
a. 1 c. .
b. / d. 0
1ow many products will result when /+butene reacts with water,
a. 1 c. .
b. / d. 0
Which organic reactant will produce .+chloropentane when reacted with hydrogen chloride,
a. pentane c. /+pentene
b. 1+pentene d. /+pentyne
Short answer
/+pentyne F e&cess 1-l
/+pentyne F / mol 1-l
/+butyne F / mol 14r
1+butyne F / mol 1-l
.+octene F hydrogen iodide
1+pentene F water
1+butene F water
.+heptene F water
0+methyl+1+butyne F 1 mol hydrogen
Organic Chemistry Testbank /?
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 hydro&ide 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 F 1+pentanol
propanol F butanoic acid
methanoic acid F 1+pentanol
1+butanol F EEEEEEEEEEEEEEEEE butyl propanoate
Hydrocarbon Combustion
When hydrocarbons are burned completely( which product is always formed,
a. amorphous graphite c. limewater
b. carbon dio&ide d. methane
Short answer
/+methyl+1+butene F o&ygen 64alance this reaction7
/+methyl+1+he&ene F o&ygen 64alance this reaction7
.+methyl+1+pentyne F o&ygen
.(0+diethyl+/+pentene F o&ygen
Elimination
Which substance will undergo an elimination reaction when reacting with hydro&ide ions,
a. /+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 Guickly with bromine( e'en in the dark,
a. acetylene c. 1+he&anol
b. /+butene d. pentane
Which reaction will not produce an alkene,
a. /+chlorohe&ane is heated with sodium hydro&ide
b. /+pentyne and hydrogen are mi&ed in the presence of a platinum catalyst
c. 1+propanol is warmed with butanoic acid in the presence of a strong acid
d. .+propanol is warmed in the presence of a strong acid
Organic Chemistry Testbank /3
Short answer
/+chlorobutane F hydro&ide ions
/+chlorobutane F sodium hydro&ide
/+pentanol is warmed in the presence of a strong acid
ethanol
H S O
/ 0

.+heptanol
H S O
/ 0


#eaction type; EEEEEEEEEEEEEEEEEEE____
)dentifying &olymeri'ation
Adentify the reaction type;
C C
OH
O O
O H
+ CH
2
CH
2
OH O H
C C
O
O O
O
CH
2
CH
2
n
n n
+
O H
2
n
a. addition polymerization c. condesation polymerization
b. esterification d. hydrocarbon combustion
Adentify the reaction type;
C C
CH
3
H H
H
n
C C
H H
H CH
3
n
a. addition polymerization c. condesation polymerization
b. esterification d. hydrocarbon combustion
What monomer was used to produce the polymer;
CH
3
CH
3
CH
3
. . .
. . .
Organic Chemistry Testbank /2
a.
C C
H
C H
3
H
CH
3
b.
C C
H
C H
3
H
H
c.
C C
CH
3
C H
3
H
CH
3
d.
C
C C H
3
H
CH
3
H
CH
3
Condensation &olymeri'ation
Which polymer was produced by condensation polymerization,
a.
O O
CH
3
CH
3
O O
n
b.
CH
3
CH
3
CH
3
CH
3
CH
3
. . . . . . . .
Organic Chemistry Testbank />
c.
CH CH
CH
3
n
d.
C C
CH
3
CH
3
H
H
n
Long answer;
Croteins are the building blocks of the human body. They are composed of chains of amino
acids( and make up our skin( nails( hair and connecti'e tissue. The type of protein formed
depends upon the seGuence of the amino acids in the chain.
Dome amino acids are gi'en below.
alanine
O
NH
2
CH
3
glycine
O
NH
2
cysteine
O
NH
2
SH
Threonine
O
NH
2
a. What type of reaction will link these amino acids into a long chained protein,
b. What are the chemical characteristics of these molecules that allow them to form
long chains, Cick one of the amino acids to illustrate your answer.
c. The protein in hair will curl around in a heli& shape( held together by hydrogen
bonds. "raw a dotted line to show where hydrogen bonding could occur if
cysteine and threonine were close together on two different protein chains. 6/7
Organic Chemistry Testbank /8
Addition Polymeriation
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. /+pentene
c. ethylmethylethane
d. pentane
Which synthetic polymer is the product of addition polymerization,
a. cellulose c. ribonucleic acid 6#5A7
b. protein d. teflon
Short answer
addition polymerization reaction with 1+pentene
addition polymerization reaction with 1+butene
n /+pentyne
Long Answer 2uestions:
When ethene reacts with chlorine in the absence of light( only one product forms. 1owe'er( if
ethene reacts with chlorine in the presence of light( o'er a long period of time( many products are
formed.
a. Adentify the reaction type when ethene reacts in the absence of light( and write
eGuation to show the product formed. 5ame and draw the product. 60:7
b. Adentify the two reaction types when ethene reacts in the presence of light( and
O
NH
2
OH
CH
3
threonine
O
NH
2
SH
cysteine
C C
H H
CH
3
CH
2
CH
3
n
Organic Chemistry Testbank .9
write an eGuation to illustrate each. 5ame and draw all possible products. 6>:7