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AP CHEMISTRY Test Booklet
3.1 Intermolecular force
1. Use the principles of atomic structure and/or chemical bonding to explain each of the following. In each part, your
answers must include references to both substances.
a. The atomic radius of Li is larger than that of Be.
b. The second ionization energy of K is greater than the second ionization energy of Ca.
c. The carbon-to-carbon bond energy in C2H4 is greater than it is in C2H6.
d. The boiling point of Cl2 is lower than the boiling point of Br2.
Please respond on separate paper, following directions from your teacher.
2.
Solid carbon tetrachloride, , is represented by the diagram above. The attractions between the
molecules that hold the molecules together in the solid state are best identified as
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(A) polar covalent bonds

(B) nonpolar covalent bonds
(C) intermolecular attractions resulting from temporary dipoles
(D) intermolecular attractions resulting from permanent dipoles
3. At 298 K and 1 atm, Br2 is a liquid with a high vapor pressure, and Cl2 is a gas. Those observations provide
evidence that under the given conditions, the
(A) forces among Br2 molecules are stronger than those among Cl2 molecules
(B) forces among Cl2 molecules are stronger than the Cl−Cl bond
(C) Br−Br bond is stronger than the Cl−Cl bond
(D) Cl−Cl bond is stronger than the Br−Br bond
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Equimolar samples of CH3OH(l) and C2H5OH(l) are placed in separate, previously evacuated, rigid 2.0 L vessels. Each
vessel is attached to a pressure gauge, and the temperatures are kept at 300 K. In both vessels, liquid is observed to remain
present at the bottom of the container at all times. The change in pressure inside the vessel containing CH3OH(l) is shown
below.
4. Compared to the equilibrium vapor pressure of CH3OH(l) at 300 K, the equilibrium vapor pressure of C2H5OH(l) at
300 K is
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(A) The same, because both compounds have hydrogen bonding among their molecules
higher, because London dispersion forces among C2H5OH molecules are greater than those among CH3OH
(B)
molecules
lower, because London dispersion forces among C2H5OH molecules are greater than those among CH3OH
(C)
molecules
(D) lower, because of the larger number of hydrogen bonds among C2H5OH molecules
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5. For parts of the free-response question that require calculations, clearly show the method used and the steps
involved in arriving at your answers. You must show your work to receive credit for your answer. Examples
and equations may be included in your answers where appropriate.
Ethanol, , will combust in air according to the equation above.
(a) Is oxidized in the reaction, or is it reduced? Justify your answer in terms of oxidation numbers.
(b) When a sample of was combusted, the volume of produced was when measured at
and . Determine the number of moles of that was produced.
(c) Determine the volume of , in , that was combusted to produce the volume of collected
in part (b). (The density of is .)
(d) Determine the amount of heat, in , that is released by the combustion reaction.
The combustion reaction occurred in a closed room containing of air originally at . Assume
that all of the heat produced by the reaction was absorbed by the air in the
room.
(e) Determine the final temperature of the air in the room after the combustion.
(f) The boiling points of ethanol and dimethyl ether are provided in the following table. Identify the intermolecular
force that is most responsible for the difference in boiling point. In terms of this force, explain why the boiling point
of ethanol is higher than that of dimethyl ether.
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Boiling
Compound Structural Formula Point
Ethanol
Dimethyl
ether
One method of producing ethanol is by the reaction of ethene and water, as represented below.
(g) A chemist wants to run the reaction and maximize the amount of produced. Identify two ways the
chemist could change the reaction conditions (other than adding or removing any chemical species) to favor the
formation of more product. Justify your answer.
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Molar Balanced Equation for the Combustion of One

Compound
Mass Mole of the Compound
Ethane
Propanol
Unknown ?
6. Based on the structural formulas, which of the following identifies the compound that is more soluble in water and
best helps to explain why?
(A) Ethane, because the electron clouds of its molecules are more polarizable than those of propanol.
Ethane, because its molecules can fit into the spaces between water molecules more easily than those of
(B)
propanol can.
(C) Propanol, because its molecules have a greater mass than the molecules of ethane have.
(D) Propanol, because its molecules can form hydrogen bonds with water molecules but those of ethane cannot.
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7. Directions: For parts of the free-response question that require calculations, clearly show the method used
and the steps involved in arriving at your answers. You must show your work to receive credit for your
answer. Examples and equations may be included in your answers where appropriate.
A student investigates properties of two compounds found in food, labeled Compound and Compound .
Structures of the compounds are shown below.
(a) Identify the hybridization of the valence orbitals of the carbon atom indicated with the arrow in the diagram of
compound .
(b) List all of the type(s) of intermolecular force(s) that the two compounds have in common.
(c) Compound has a greater boiling point than compound . The student claims that the difference is because
compound exhibits stronger hydrogen bonding than compound . Do you agree or disagree with this claim?
Justify your answer in terms of the types and relative strengths of intermolecular forces in each substance.
A different compound found in food, compound , is known to decompose over time. To study the reaction, a
student monitors the molar concentration of compound in a solution at constant temperature. After collecting
and analyzing the data, the following linear graph was created by plotting versus time.
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(d) The student proposes that the reaction is second order with respect to compound . Do you agree or disagree?
Justify your answer using the data in the graph above.
(e) Write the rate law expression for the decomposition of compound that is consistent with the graph above.
(f) Determine the value of the rate constant, , for the reaction. Include units with your answer.
(g) The student claims that if the experiment were conducted again at a higher temperature, the value for the rate
constant, , would decrease. Do you agree or disagree with the student’s claim? Justify your answer by comparing
the slope of the original line above to the slope that would result from the higher temperature conditions.
A student titrates a solution of compound to determine the concentration of in the solution. In order to
conduct the titration, the student needs to prepare of by diluting a stock
solution.
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(h) What volume of stock solution, in , would be required to prepare of

?
(i) To prepare the diluted solution, the student uses a graduated cylinder to measure the volume of stock solution
calculated in part (h) and adds it to a volumetric flask, followed by the addition of distilled water. If
the student spilled some of the stock solution while transferring it to the volumetric flask and continues to fill it to
the line with distilled water, would the resulting solution have a concentration that is greater than, less than, or
equal to the intended concentration? Justify your answer.
The ion can be reduced to form elemental iodine. Three possible mass spectra for a sample of atomic
iodine ( ) are represented below.
(j) Identify the mass spectrum that represents the isotopes of iodine. Justify your choice.
Iodine can react with a certain element, . The successive ionization energy values for element are given
below.
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Ionization Energy ( )
First 578
Second 1817
Third 2745
Fourth 11,578
Fifth 14,842
(k) What is the charge of the ion formed by element in its compounds? Justify your answer using the data in the
table.
(l) Given the charge determined in part (k), what is the formula for the compound that element would form
with iodine?
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(a) Using theory, predict the bond angle indicated by the arrow in the diagram of
compound .
(c) Compound has a higher boiling point than compound . The student claims that compound has a greater
boiling point because it has greater London dispersion forces than compound . Do you agree or disagree with
this claim? Justify your answer in terms of the types and relative strengths of intermolecular forces in each
substance.
A different compound found in food, compound is known to decompose over time. To study the reaction, a
student monitors the molar concentration of compound in a solution at constant temperature. After collecting
and analyzing the data, the following linear graph was created by plotting versus time.
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(d) The student proposes that the reaction is zero order with respect to compound . Do you agree or disagree?
(g) The student claims that if the experiment were conducted again at a higher temperature, the value for the rate
constant, , would increase. Do you agree or disagree with the student’s claim? Justify your answer by comparing
the slope of the original line above to the slope that would result from the higher temperature conditions.
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solution.

?
the student filled the volumetric flask with distilled water but the bottom of the meniscus was significantly above
the mark, would the resulting solution concentration be greater than, less than, or equal to what was
intended? Justify your answer.
(j) Identify the mass spectrum that most likely represents the isotopes of iodine. Justify your choice.
Iodine can also react with a certain element, . The successive ionization energy values for element are given
below.
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Ionization Energy ( )
First 419
Second 3051
Third 4419
Fourth 5878
Fifth 7975
table.
with iodine?
9.
Based on the information in the table above, which of the compounds has the highest boiling point, and why?
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(A) Butanal, because it can form intermolecular hydrogen bonds

(B) Pentane, because it has the longest carbon chain
(C) Pentane, because it has the most C−H bonds
(D) Propanoic acid, because it can form intermolecular hydrogen bonds
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(a) Identify the hybridization of the valence orbitals of the carbon atom indicated with the arrow in the diagram of
compound .
(c) Compound has a greater boiling point than compound . The student claims that the difference is because
compound exhibits hydrogen bonding, but compound does not. Do you agree or disagree with this claim?
Justify your answer in terms of the types and relative strengths of intermolecular forces in each substance.
To show that compound present in food is lost over time, a student monitors the molar concentration of
compound in a solution at constant temperature. After collecting and analyzing the data, the following linear
graph was created by plotting versus time.
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(d) The student proposes that the reaction is first order with respect to compound . Do you agree or disagree?
(g) The student claims that if the experiment were conducted again at a lower temperature, the value for the rate
constant, , would decrease. Do you agree or disagree with the student’s claim? Justify your answer by comparing
the slope of the original line above to the slope that would result from the lower temperature conditions.
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solution.

?
the student fills the volumetric flask with distilled water, but the bottom of the meniscus is significantly below the
mark, would the resulting solution concentration be greater than, less than, or equal to the intended
concentration? Justify your answer.
(j) Identify the mass spectrum that represents the isotopes of iodine. Justify your choice.
Iodine can react with a certain element, . The successive ionization energy values for element are given
below.
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Ionization Energy
( )
First 738
Second 1451
Third 7733
Fourth 10,542
Fifth 13,636
table.
with iodine?
Questions refer to three gases in identical rigid containers under the conditions given in the table below.
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11. If the pressure of each gas is increased at constant temperature until condensation occurs, which gas will condense
at the lowest pressure?
(A) Methane
(B) Ethane
(C) Butane
(D) All the gases will condense at the same pressure.
Refer to three gases in identical rigid containers under the conditions given in the table below.
12. If the pressure of each gas is increased at constant temperature until condensation occurs, which gas will condense
at the lowest pressure?
(A) Methane
(B) Ethane
(C) Butane
(D) All the gases will condense at the same pressure.
13.
The structural formulas for two isomers of are shown above. Which of the two liquids has
the higher equilibrium vapor pressure at , and why?
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The cis-isomer, because it has dipole-dipole interactions, whereas the trans-isomer has only London
(A)
dispersion forces
The cis-isomer, because it has only London dispersion forces, whereas the trans-isomer also has dipole-
(B)
dipole interactions
The trans-isomer, because it has dipole-dipole interactions, whereas the cis-isomer has only London
(C)
dispersion forces
The trans-isomer, because it has only London dispersion forces, whereas the cis-isomer also has dipole-
(D)
dipole interactions
14. The London (dispersion) forces are weakest for which of the following gases under the same conditions of
temperature and pressure?
(A) H2
(B) O2
(C) Xe
(D) F2
(E) N2
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15.
The diagram above is a molecular model of a gaseous diatomic element that is just above its boiling point.
Intermolecular forces between the gas molecules will cause them to condense into the liquid phase if the
temperature is lowered. Which of the following best describes how the model is limited in its depiction of the
phenomenon?
It does not show how hydrogen bonds are constantly forming, breaking, and reforming, which results in a net
(A)
force of attraction between the molecules.
It does not show how the interactions between ions and the induced molecular dipoles result in a net force of
(B)
attraction between the molecules.
It does not show how the interacting permanent dipoles of the molecules result in a net force of attraction
(C)
between the molecules.
It does not show how the temporary fluctuating dipoles of the molecular electron clouds result in a net force
(D)
of attraction between the molecules.
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Directions: Each set of lettered choices below refers to the numbered statements immediately following it. Select the one
lettered choice that best fits each statement. A choice may be used once, more than once, or not at all in each set.
(A) A network solid with covalent bonding

(B) A molecular solid with zero dipole moment
(C) A molecular solid with hydrogen bonding
(D) An ionic solid
(E) A metallic solid
16. Solid ethyl alcohol, C2H5OH

(A) A network solid with covalent bonding
(B) A molecular solid with zero dipole moment
(C) A molecular solid with hydrogen bonding
(D) An ionic solid
(E) A metallic solid
17.
Consider the molecules represented above and the data in the table below.
Nonane and 2,3,4-trifluoropentane have almost identical molar masses, but nonane has a significantly higher boiling
point. Which of the following statements best helps explain this observation?
(A) The C-F is easier to break than the C-H bond.
(B) The C-F is more polar than the C-H bond.
(C) The carbon chains are longer in nonane than they are in 2,3,4-trifluoropentane.
(D) The carbon chains are farther apart in a sample of nonane than they are in 2,3,4-trifluoropentane.
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18.
Consider the molecules represented above and the data in the table below.
Nonane and 2,3,4-trifluoropentane have almost identical molar masses, but nonane has a significantly higher boiling
point. Which of the following statements best helps explain this observation?
(A) The C–F bond is easier to break than the C–H bond.
(B) The C–F bond is more polar than the C–H bond.
(C) The carbon chains are longer in nonane than they are in 2,3,4-trifluoropentane.
(D) The carbon chains are farther apart in a sample of nonane than they are in 2,3,4- trifluoropentane.
19. Which of the following best helps to explain why CCl4 is a liquid whereas CI4 is a solid when both are at 25°C?
The dipole moment of the CCl4 molecule is larger than that of the CI4 molecule because Cl is more
(A)
electronegative than I.
The dipole moment of the CI4 molecule is larger than that of the CCl4 molecule because there is stronger
(B)
repulsion between electrons in the C-I bonds compared to the repulsion between electrons in the C- Cl bonds.
(C) The London dispersion forces are stronger in CCl4 than in CI4 because Cl is more electronegative than I.
The London dispersion forces are stronger in CI4 than in CCl4 because CI4 has a more polarizable electron
(D)
cloud than CCl4
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20. Using principles of atomic and molecular structure and the information in the table below, answer the following
questions about atomic fluorine, oxygen, and xenon, as well as some of their compounds.
(a) Write the equation for the ionization of atomic fluorine that requires 1,681.0 kJ mol−1.
(b) Account for the fact that the first ionization energy of atomic fluorine is greater than that of atomic oxygen.
(You must discuss both atoms in your response.)
(c) Predict whether the first ionization energy of atomic xenon is greater than, less than, or equal to the first
ionization energy of atomic fluorine. Justify your prediction.
(d) Xenon can react with oxygen and fluorine to form compounds such as XeO3 and XeF4 . In the boxes provided,
draw the complete Lewis electron-dot diagram for each of the molecules represented below.
(e) On the basis of the Lewis electron-dot diagrams you drew for part (d), predict the following:
(i) The geometric shape of the XeO3 molecule

(ii) The hybridization of the valence orbitals of xenon in XeF4
(f) Predict whether the XeO3 molecule is polar or nonpolar. Justify your prediction.
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21.
Based on Coulomb’s Law and the information in the table above, which of the following cations is most likely to
have the weakest interaction with an adjacent water molecule in an aqueous solution?
(A) Li+
(B) Na+
(C) Ca2+
(D) In3+
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22. Answer each of the following in terms of principles of molecular behavior and chemical concepts.
a. The structures for glucose, C6H12O6 , and cyclohexane, C6H12 , are shown below.
Identify the type(s) of intermolecular attractive forces in
i. pure glucose
ii. pure cyclohexane
b. Glucose is soluble in water but cyclohexane is not soluble in water. Explain.
c. Consider the two processes represented below.
Process 1: H2O(l) → H2O(g) ∆H° = +44.0 kJ mol−1
Process 2: H2O(l) → H2(g) + ½ O2(g) ∆H° = +286 kJ mol−1
i. For each of the two processes, identify the type(s) of intermolecular or intramolecular attractive
forces that must be overcome for the process to occur.
ii. Indicate whether you agree or disagree with the statement in the box below. Support your
answer with a short explanation.
When water boils, H2O molecules break apart to form hydrogen molecules and oxygen
molecules.
d. Consider the four reaction-energy profile diagrams shown below.
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i. Identify the two diagrams that could represent a catalyzed and an uncatalyzed reaction pathway
for the same reaction. Indicate which of the two diagrams represents the catalyzed reaction
pathway for the reaction.
ii. Indicate whether you agree or disagree with the statement in the box below. Support your
answer with a short explanation.
Adding a catalyst to a reaction mixture adds energy that causes the reaction to proceed more
quickly.
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The structure of haloacetic acids, (where is either , , , or ), is shown above. The dissociation
constants and molar masses of four haloacetic acids are listed in the table below.
Acid Molar Mass

Fluoroacetic acid
Chloroacetic acid
Bromoacetic acid
Iodoacetic acid
23. Which compound, chloroacetic acid or iodoacetic acid, most likely has the lower boiling point, and why?
(A) Chloroacetic acid, because the London dispersion forces among its molecules are weaker.
(B) Chloroacetic acid, because the dipole-dipole forces among its molecules are weaker.
(C) Iodoacetic acid, because the London dispersion forces among its molecules are stronger.
(D) Iodoacetic acid, because the dipole-dipole forces among its molecules are stronger.
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24. For parts of the free-response question that require calculations, clearly show the method used and the steps
involved in arriving at your answers. You must show your work to receive credit for your answer. Examples and
equations may be included in your answers where appropriate.
Answer the following questions relating to the chemistry of the halogens.
(a) The molecular formulas of diatomic bromine, chlorine, fluorine, and iodine are written below. Circle the
formula of the molecule that has the longest bond length. Justify your choice in terms of atomic structure.
A chemistry teacher wants to prepare . The teacher has access to the following three reagents: ,
, and .
Half-Reaction at
(b) Using the data in the table above, write the balanced equation for the thermodynamically favorable reaction
that will produce when the teacher combines two of the reagents. Justify that the reaction is
thermodynamically favorable by calculating the value of for the reaction.
and can react to form the compound .
(c) The boiling point of is , whereas the boiling point of is . Explain this difference in
boiling point in terms of all the intermolecular forces present between molecules of each substance.
The compound can decompose into and , as represented by the balanced chemical equation
below.
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A mole sample of pure is placed in a previously evacuated, rigid container at .

Eventually the system reaches equilibrium according to the equation above.
(d) Calculate the pressure in the container before equilibrium is established.
(e) Write the expression for the equilibrium constant, , for the decomposition of .
After the system has reached equilibrium, percent of the original sample has decomposed.
(f) Determine the value of for the decomposition reaction of at .
(g) Calculate the bond energy of the bond, in , using for the reaction
and the information in the following table.
Bond Bond Energy
25.
Substance Normal boiling point
The electron cloud of is smaller than that of , however, has a much higher boiling point than has.
Which of the following explains how the dispersion-force model of intermolecular attraction does not account for
the unusually high boiling point of ?
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(A) is soluble in water, whereas is insoluble in water.

(B) The molecule has a greater mass than the molecule has.
Liquid has weak dispersion force attractions between its molecules, whereas liquid has strong ionic
(C)
interactions between and ions.
Liquid has weak dispersion force attractions between its molecules, whereas liquid has both weak
(D)
dispersion force attractions and hydrogen bonding interactions between its molecules.
26.
Four different liquid compounds in flasks at are represented above. The table below identifies the
compounds. Flask C shows the most particles in the vapor phase. Which of the following is not shown in the model
but best helps to explain why flask C must contain pentane?
Name Chemical Formula Boiling Point

Pentane 36
Hexane 69
Heptane 98
Octane 126
(A) The random motion of the particles within the liquids

(B) The relative speeds of the vapor particles in each flask
(C) The strength of the intermolecular forces between the particles in the liquids
(D) The structural formula of the molecules of the liquid and vapor in each flask
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27.
The molecular formula and molar mass of two straight-chain hydrocarbons are listed in the table above. Based on
the information in the table, which compound has the higher boiling point, and why is that compound’s boiling
point higher?
(A) C4H10 ,because it has more hydrogen atoms, resulting in more hydrogen bonding
(B) C4H10 , because it has more electrons, resulting in greater polarizability and stronger dispersion forces
C2H6 , because its molecules are smaller and they can get closer to one another, resulting in stronger
(C)
dispersion forces
(D) C2H6 , because its molecules are more polar, resulting in stronger dipole-dipole attractions
28. Thymine and adenine form a base pair in the DNA molecule. These two bases can form a connection between two
strands of DNA via two hydrogen bonds. Which of the following diagrams shows the correct representation of the
hydrogen bonding (denoted by dashed lines) between thymine and adenine base pairs? (In each diagram, thymine is
shown at the left and adenine is shown at the right. The bases are attached to the backbone portion of the DNA
strands.)
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(A)
(B)
(C)
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(D)
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29. Answer the following questions by using principles of molecular structure and intermolecular forces.
(a) Structures of the pyridine molecule and the benzene molecule are shown below. Pyridine is soluble in water,
whereas benzene is not soluble in water. Account for the difference in solubility. You must discuss both of the
substances in your answer.
(b) Structures of the dimethyl ether molecule and the ethanol molecule are shown below. The normal boiling point
of dimethyl ether is 250 K, whereas the normal boiling point of ethanol is 351 K. Account for the difference in
boiling points. You must discuss both of the substances in your answer.
(c) SO2 melts at 201 K, whereas SiO2 melts at 1,883 K. Account for the difference in melting points. You must
discuss both of the substances in your answer.
(d) The normal boiling point of Cl2 (l) (238 K) is higher than the normal boiling point of HCl(l) (188 K). Account
for the difference in normal boiling points based on the types of intermolecular forces in the substances. You must
discuss both of the substances in your answer.
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30.
Benzene, C6H6 , has the structure shown above. Considering the observation that benzene is only sparingly soluble
in water, which of the following best describes the intermolecular forces of attraction between water and benzene?
(A) Benzene is nonpolar, therefore there are no forces between water and benzene.
(B) The H atoms in benzene form hydrogen bonds with the O atoms in water.
(C) Benzene is hydrophobic, therefore there is a net repulsion between water and benzene.
(D) There are dipole-induced dipole and London dispersion interactions between water and benzene.
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31.
The diagram above represents a particle in aqueous solution. Which of the following statements about the particle is
correct?
(A) The particle must be a cation because the negative end of each water molecule is pointed toward it.
(B) The particle must be an anion because the positive end of each water molecule is pointed toward it.
(C) The charge of the particle cannot be determined because water molecules have no net charge.
The charge of the particle cannot be determined because the water molecules are arranged symmetrically and
(D)
their partial charges cancel.
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32.
Based on Coulomb’s law and the information in the table above, which of the following anions is most likely to
have the strongest interactions with nearby water molecules in an aqueous solution?
(A) Cl-
(B) I-
(C) S2-
(D) Te2-
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A student investigates the physical and chemical properties of various carbon-containing compounds. The
complete Lewis electron-dot diagrams and boiling points for two compounds, and , are shown in the
following table.
(a) Identify the hybridization of the valence orbitals of the carbon atom in compound that is indicated by the
arrow in the diagram.
(b) The bond in compound is longer than any bond in compound . Explain the reason for this
difference using principles of atomic structure.
(c) For each compound, list all intermolecular forces present.
Compound –
Compound –
(d) Explain why the boiling point of compound is higher than that of compound based on the types and
relative strengths of the intermolecular forces present in each substance.
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(e) A sample of compound is placed in an evacuated, rigid container at and . When

more moles of compound are added, the pressure increases to at . Determine the number of
moles of compound now present in the container.
Another carbon-containing compound is , which reacts with , as represented by the following

equation.
(f) The student claims that is oxidized when is converted to . Do you agree or disagree?
Justify your answer in terms of oxidation numbers.
The reaction is known to be exothermic. A proposed mechanism for the reaction is shown in the following table.
Step 1 fast
Step 2 slow
(g) The student draws the following energy diagram for the reaction. Is the drawing consistent with the proposed
mechanism? Justify your answer.
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(h) The reaction is run in an excess of such that remains constant. The student claims that
under these conditions, the reaction is zeroth-order with respect to , and that the rate constant of the
reaction is . Is the following graph consistent with the student’s claim? Justify your answer with
respect to the graph’s axes and the numerical value of the slope of the line.
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complete Lewis electron-dot diagrams and boiling points for two compounds, and , are shown in the following
table.
(a) Based on theory, what is the approximate value of the bond angle in compound ?
(b) The bond in compound is shorter than the bond in compound . Explain the reason for this
Compound –
Compound –
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(e) A gaseous sample of compound is placed in an evacuated, rigid container at a temperature of and a
pressure of . Determine the final pressure when the temperature of the sample is increased to .

equation.
Step 1 fast
Step 2 slow
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under these conditions, the reaction is first-order with respect to , and that the rate constant of the reaction
is . Is the following graph consistent with the student’s claim? Justify your answer with respect to the
graph’s axes and the numerical value of the slope of the line.
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35. Answer the following questions in terms of principles of chemical bonding and intermolecular forces. In each
explanation where a comparison is to be made, a complete answer must include a discussion of both substances.
The following complete Lewis electron-dot diagrams may be useful in answering parts of this question.
a. At 1 atm and 298 K, pentane is a liquid whereas propane is a gas. Explain.
b. At 1 atm and 298 K, methanol is a liquid whereas propane is a gas. Explain.
c. Indicate the hybridization of the carbon atom in each of the following:
i. Methanol
ii. Methanoic (formic) acid
d. Draw the complete Lewis electron-dot diagram for a molecule of propanoic acid, HC3H5O2 .
e. Explain the following observations about the two carbon-oxygen bonds in the methanoate (formate)
anion, HCO2−. You may draw a Lewis electron-dot diagram (or diagrams) of the methanoate ion as part
of your explanations.
i. The two carbon-oxygen bonds in the methanoate (formate) anion, HCO2−, have the same
length.
ii. The length of the carbon-oxygen bonds in the methanoate (formate) anion, HCO2−, is
intermediate between the length of the carbon-oxygen bond in methanol and the length of the
carbon-oxygen bond in methanal.
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36. A student places a mixture of plastic beads consisting of polypropylene (PP) and polyvinyl chloride (PVC) in a 1.0
L beaker containing distilled water. After stirring the contents of the beaker vigorously, the student observes that
the beads of one type of plastic sink to the bottom of the beaker and the beads of the other type of plastic float on
the water. The chemical structures of PP and PVC are represented by the diagrams below, which show segments
of each polymer.
a. Given that the spacing between polymer chains in PP and PVC is similar, the beads that sink are made of
which polymer ? Explain.
PP is synthesized from propene, C3H6, and PVC is synthesized from vinyl chloride, C2H3Cl. The
structures of the molecules are shown below.
b. The boiling point of liquid propene (226 K) is lower than the boiling point of liquid vinyl chloride (260
K). Account for this difference in terms of the types and strengths of intermolecular forces present in
each liquid.
In a separate experiment, the student measures the enthalpies of combustion of propene and vinyl
chloride. The student determines that the combustion of 2.00 mol of vinyl chloride releases 2300 kJ of
energy, according to the equation below.
2 C2H3Cl(g) + 5 O2(g) → 4 CO2(g) + 2 H2O(g) + 2 HCl(g) ∆H° = -2300 kJ/molrxn
c. Using the table of standard enthalpies of formation below, determine whether the combustion of 2.00 mol
of propene releases more, less, or the same amount of energy that 2.00 mol of vinyl chloride releases.
Justify your answer with a calculation. The balanced equation for the combustion of 2.00 mol of propene
is 2 C3H6(g) + 9 O2(g) → 6 CO2(g) + 6 H2O(g).
Test Booklet
37.
In the diagram above, which of the labeled arrows identifies hydrogen bonding in water?
(A) A
(B) B
(C) C
(D) D
Test Booklet
38. Directions: Examples and equations may be included in your responses where appropriate. For calculations,
clearly show the method used and the steps involved in arriving at your answers. You must show your work to
receive credit for your answer. Pay attention to significant figures
Propanoic acid, C2H5COOH, is an organic acid that is a liquid at room temperature.
(a) An incomplete Lewis diagram for the propanoic acid molecule is provided in the box below. Complete
the diagram, showing how the remaining atoms in the molecule are arranged around the carbon atom
marked with an asterisk (*). Your structure should minimize formal charge and include any lone pairs of
electrons.
(b) Identify the hybridization of the carbon atom marked with the asterisk
(c) Propanoic acid has a lower boiling point than butanoic acid, C3H7COOH.
i. Identify all the types of intermolecular forces present among the molecules in propanoic acid.
ii. Which of the types of intermolecular forces that you identified in part (c)(i) is most responsible for the
difference in boiling points of the two acids?
Test Booklet
following table.
(b) The bonds in compound are shorter than the bonds in compound . Explain the reason for
this difference using principles of atomic structure.
Compound –
Compound –
Test Booklet
(e) A gaseous sample of compound is placed in an evacuated cylinder with a movable piston that can change
the volume of the cylinder. The initial volume and temperature of the gas are and . If the
temperature of the gas is raised to as its pressure remains constant, what is the final volume of the gas?

equation.
(f) The student claims that is reduced when is converted to . Do you agree or disagree?
Step 1 fast
Step 2 slow
Test Booklet
under these conditions, the reaction is second-order with respect to , and that the rate constant of the
reaction is . Is the following graph consistent with the student’s claim? Justify your answer
with respect to the graph’s axes and the numerical value of the slope of the line.
Test Booklet
Test Booklet
following table.
(b) Any bond in compound is shorter than the bond in compound . Explain the reason for this
Compound –
Compound –
Test Booklet
(e) A gaseous sample of compound is placed in an evacuated cylinder with a movable piston. If the initial
pressure in the cylinder is , determine the new pressure when the volume is increased to at
constant temperature.

equation.
Step 1 fast
Step 2 slow
Test Booklet
under these conditions, the reaction is first-order with respect to and that the rate constant of the reaction
is . Is the following graph consistent with the student’s claim? Justify your answer with respect to the
graph’s axes and the numerical value of the slope of the line.
Test Booklet
41.
Based on the data in the table above, which of the following correctly predicts the relative strength of the attraction
of Zn2+, Ca2+, and Ba2+ ions to water molecules in a solution, from strongest to weakest, and provides the correct
reason?
(A) Zn2+ > Ca2+ > Ba2+ because the smaller ions have a stronger coulombic attraction to water
(B) Zn2+ > Ca2+ > Ba2+ because the smaller ions are more electronegative
(C) Ba2+ > Ca2+ > Zn2+ because the larger ions are more polarizable
(D) Ba2+ > Ca2+ > Zn2+ because the larger ions are less electronegative
Test Booklet
42. Answer the following questions related to sulfur and one of its compounds.
a. Consider the two chemical species S and S2- .
i. Write the electron configuration (e.g., 1s2 2s2 . . .) of each species.
ii. Explain why the radius of the S2− ion is larger than the radius of the S atom.
iii. Which of the two species would be attracted into a magnetic field? Explain.
b. The S2- ion is isoelectronic with the Ar atom. From which species, S2- or Ar, is it easier to remove an
electron? Explain.
c. In the H2S molecule, the H–S–H bond angle is close to 90°. On the basis of this information, which
atomic orbitals of the S atom are involved in bonding with the H atoms?
d. Two types of intermolecular forces present in liquid H2S are London (dispersion) forces and dipole-
dipole forces.
i. Compare the strength of the London (dispersion) forces in liquid H2S to the strength of the
London (dispersion) forces in liquid H2O. Explain.
ii. Compare the strength of the dipole-dipole forces in liquid H2S to the strength of the dipole-
dipole forces in liquid H2O. Explain.
43.
Which of the following is the strongest type of interaction that occurs between the atoms within the circled areas of
the two molecules represented above?
Test Booklet
(A) Polar covalent bond

(B) Nonpolar covalent bond
(C) Hydrogen bond
(D) London dispersion forces
Test Booklet
44.
Using the information in the table above, answer the following questions about organic compounds.
a. For propanone,
i. draw the complete structural formula (showing all atoms and bonds);
ii. predict the approximate carbon-to-carbon-to-carbon bond angle.
b. For each pair of compounds below, explain why they do not have the same value for their standard heat
of vaporization, ΔH°vap, (You must include specific information about both compounds in each pair.)
i. Propane and propanone
ii. Propanone and 1-propanol
c. Draw the complete structural formula for an isomer of the molecule you drew in part (a) (i).
d. Given the structural formula for propyne below,
i. indicate the hybridization of the carbon atom indicated by the arrow in the structure above;
ii. indicate the total number of sigma (σ) bonds and the total number of pi (⯑) bonds in the
molecule.
Test Booklet
45. Use the information in the table below to respond to the statements and questions that follow. Your answers
should be in terms of principles of molecular structure and intermolecular forces.
a. Draw the complete Lewis electron-dot diagram for ethyne in the appropriate cell in the table above.
b. Which of the four molecules contains the shortest carbon-to-carbon bond? Explain.
c. A Lewis electron-dot diagram of a molecule of ethanoic acid is given below. The carbon atoms in the
molecule are labeled x and y, respectively.
Identify the geometry of the arrangement of atoms bonded to each of the following.
i. Carbon x
ii. Carbon y
d. Energy is required to boil ethanol. Consider the statement “As ethanol boils, energy goes into breaking
C−C bonds, C−H bonds, C−O bonds, and O−H bonds.” Is the statement true or false? Justify your
answer.
e. Identify a compound from the table above that is nonpolar. Justify your answer.
f. Ethanol is completely soluble in water, whereas ethanethiol has limited solubility in water. Account for
the difference in solubilities between the two compounds in terms of intermolecular forces.
Test Booklet
46. In which of the following liquids do the intermolecular forces include dipole-dipole forces?
(A) F2(l)
(B) CH4(l)
(C) CF4(l)
(D) CH2F2(l)
Test Booklet
following table.
(a) Based on theory, what is the approximate value of the bond angle in compound ?
b) The bond in compound is shorter than the bond in compound . Explain the reason for this
Compound –
Compound –
Test Booklet
(e) A gaseous sample of compound is placed in an evacuated, rigid container at a temperature of and a
pressure of . Determine the final pressure of the gas when the temperature is decreased to .

equation.
(f) The student claims that is reduced when is converted to . Do you agree or disagree? Justify
your answer in terms of oxidation numbers.
Step 1 fast
Step 2 slow
Test Booklet
under these conditions, the reaction is zeroth-order with respect to , and that the rate constant of the
reaction is . Is the following graph consistent with the student’s claim? Justify your answer with
respect to the graph’s axes and the numerical value of the slope of the line.
Test Booklet

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AP CHEMISTRY Test Booklet

3.1 Intermolecular force

a. The atomic radius of Li is larger than that of Be.

c. The carbon-to-carbon bond energy in C2H4 is greater than it is in C2H6.

Please respond on separate paper, following directions from your teacher.

3.1 Intermolecular force

(A) polar covalent bonds

3.1 Intermolecular force

3.1 Intermolecular force

3.1 Intermolecular force

Ethanol, , will combust in air according to the equation above.

Please respond on separate paper, following directions from your teacher.

Please respond on separate paper, following directions from your teacher.

Please respond on separate paper, following directions from your teacher.

Please respond on separate paper, following directions from your teacher.

Please respond on separate paper, following directions from your teacher.

3.1 Intermolecular force

Please respond on separate paper, following directions from your teacher.

3.1 Intermolecular force

Please respond on separate paper, following directions from your teacher.

Molar Balanced Equation for the Combustion of One

3.1 Intermolecular force

Please respond on separate paper, following directions from your teacher.

Please respond on separate paper, following directions from your teacher.

Please respond on separate paper, following directions from your teacher.

3.1 Intermolecular force

Please respond on separate paper, following directions from your teacher.

Please respond on separate paper, following directions from your teacher.

Please respond on separate paper, following directions from your teacher.

Please respond on separate paper, following directions from your teacher.

3.1 Intermolecular force

(h) What volume of stock solution, in , would be required to prepare of

Please respond on separate paper, following directions from your teacher.

Please respond on separate paper, following directions from your teacher.

Please respond on separate paper, following directions from your teacher.

3.1 Intermolecular force

Please respond on separate paper, following directions from your teacher.

Please respond on separate paper, following directions from your teacher.

3.1 Intermolecular force

Please respond on separate paper, following directions from your teacher.

Please respond on separate paper, following directions from your teacher.

Please respond on separate paper, following directions from your teacher.

3.1 Intermolecular force

Please respond on separate paper, following directions from your teacher.

Please respond on separate paper, following directions from your teacher.

Please respond on separate paper, following directions from your teacher.

Please respond on separate paper, following directions from your teacher.

3.1 Intermolecular force

(h) What volume of stock solution, in , would be required to prepare of

Please respond on separate paper, following directions from your teacher.

Please respond on separate paper, following directions from your teacher.

Please respond on separate paper, following directions from your teacher.

3.1 Intermolecular force

Please respond on separate paper, following directions from your teacher.

Please respond on separate paper, following directions from your teacher.

3.1 Intermolecular force

(A) Butanal, because it can form intermolecular hydrogen bonds

3.1 Intermolecular force

Please respond on separate paper, following directions from your teacher.