MCAT Subject Tests

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____________________________________________________

ORGANIC

CHEMISTRY SUBJECT TEST1

Organic Chemistry Subject Test 1

3.
1.

The least stable free radical is

A.

Which resonance structure for acrolein would be

expected to make the LEAST contribution to the actual
hybrid?
A.

H C

CH2 CH

CH

CH2 CH

CH

CH2 CH

CH

CH2 CH

CH

B.

B.

C.

CH
3

H 3C

CH
3

D.

C.

H
H 3C C

E. All of the above would make an equal contribution

to the hybrid.

H
D.

4.

H3 C

A. CH3CH2OH
B. CH3CH2CH2OH
C.

E.

CH2 CH

Which of the following would be most soluble in water?

CH2

O
CH3CCH3

2.

Which of the following is the most stable carbanion?

( = phenyl group)
A.
B.
C.
D.
E.

3C:
2HC:
H2C:
H3C:
(CH3)3C:

D. H2C=CHCH3
E. CH3OCH2CH3
5.

Which of the following has the lowest heat of

hydrogenation per mole of H2 absorbed?
A.
B.
C.
D.
E.

1,3-pentadiene
1,4-pentadiene
1,2-pentadiene
1,3,5-hexatriene
1,2,4-hexatriene

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8. Sulfanilic acid, illustrated below, can be recrystallized
from hot water and has an extremely high melting point
6. When an optically active sample of 2-bromobutane,
(288oC) relative to its molecular weight (173.2).
depicted below, reacts with I in an aprotic solvent,
second order kinetics is observed. Which of the
following statements must be true?
SO3H
CH2CH3

Br

H 2N
The best explanation for the physical properties
mentioned is that

A. The reactant has R stereochemistry while the

product has S stereochemistry.
B. The reactant has S stereochemistry while the
product has R stereochemistry.
C. Both reactant and product have the same R/S
designation.
D. The product is a racemic mixture of R and S
enantiomers.
E. The product is optically inactive.
7.

Which of the following is an amide?

A. the amino group of sulfanilic acid acts as a Lewis

acid.
B. sulfanilic acid exists as a pair of enantiomers.
C. sulfanilic acid exists as a pair of diastereomers.
D. sulfanilic acid exists as a zwitterion.
E. the sulfur atom of sulfanilic acid has an unusually
low oxidation number.
9.

Which of the following has the lowest boiling point?

A.
B.
C.
D.
E.

A.

NH2

n-butane
isobutane
cis-2-butene
1-butyne
2-butanol

10. Which of the following has the highest boiling point?

CH3

A.
B.
C.
D.
E.

B.

CH3(CH2)2CH3
(CH3)2CHCH2CH3
CH3(CH2)3CH3
(CH3)2CHCH3
CH3CH2CH3

N(CH3)2
C.

11. Which of the following has the highest melting point?

N
H
D. N(CH3)3

A.
B.
C.
D.
E.

trans-2-butene
cis-2-butene
n-butane
1-propanol
1-pentanol

E.

CH3

NO2

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14.
12. Which of the structures pictured below corresponds to
2-methoxy-3-butenal?

ORGANIC

CHO

OH

A.

CH2 CH

OH

OH

OH
CHO

The two molecules pictured above are

OCH3
C

CHO

CHO

CH3

B.

CH3 CH

CHEMISTRY SUBJECT TEST1

A.
B.
C.
D.
E.

O
C.

meso structures.
enantiomers.
diastereomers.
identical.
racemates.

OCH3
CH3 CH

CH3

15. Which of the following will be least reactive towards

SN1 substitution?

A.

D.

H
CH2 CH

O
H

OCH3 H

Br

H
B.

E.

OCH3
CH3 CH

CH3

O
CH

CH

CH3 CH2 C

Br

H
13. Which of the following statements is true regarding the
relative boiling points of cis- and trans- 1,2dichloroethene?
A. The boiling point of the cis isomer is higher because
it has a net dipole moment.
B. The boiling point of the cis isomer is higher because
it is thermodynamically more stable.
C. The boiling point of the trans isomer is higher
because the _ electrons are more delocalized.
D. The boiling point of the trans isomer is higher
because it is more symmetrical.
E. The boiling point of the two will be equal because
cis and trans isomers have identical physical
properties.

C.

CH3
CH3 C

Br

CH3
D.

CH2 CH3
CH3 CH2 C

Br

H
E.

H
CH3 CH2 C

Br

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16. Which of the following is true regarding SN1 and
SN2 reactions?
19. Which of the following statements is true about the
A. SN1 reactions proceed via a carbocation
compounds pictured below?
intermediate; SN2 reactions do so under certain
CH3
CH3
conditions.
B. Both SN1 and SN2 reactions can yield
Cl
H
H
Cl
rearrangement products.
C. SN1 reactions proceed more readily with a tertiary
H
Cl
Cl
H
alkyl halide as reactant; SN2 reactions proceed more
readily with a primary alkyl halide as reactant.
CH2CH3
CH2CH3
D. The rates of SN1 reactions are largely affected by
A. They are diastereomers with different melting
steric factors; the rates of SN2 reactions are largely
points.
affected by electronic factors.
B.
They are diastereomers with identical boiling
E. Protic solvents favor SN2 over SN1 reactions.
points.
C. They are enantiomers with different melting points.
17. Which of the compounds below has the highest melting
D. They are enantiomers which rotate plane-polarized
point?
light in different directions.
E. They are identical meso structures.
A. CH (CH ) COOH

B.
C.
D.
E.

2 4

CH3(CH2)4CH3
CH2=CH(CH2)3CH3
CH3(CH2)4CH2OH
CH3(CH2)2CH2OH

20. Which of the following statements is true about the

compounds pictured below?

CH3

18. Which of the structures below corresponds to 3-cyano2-butenoyl chloride?

A.

H3C

A.
B.
C.
D.
E.

C
Cl

B.

H3C

Br

Br

Br

Br

CH3

CH3

CH3

They are enantiomers and are optically active.

They are diastereomers and are optically active.
They are diastereomers and are optically inactive.
They are meso structures and are optically active.
They are meso structures and are optically inactive.

O
Cl

H
C.

H3C

CH2Cl

H
D.

H3C

CH2Cl

H
E.

H3C

O
C
Cl

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21. What is(are) the major organic product(s) of the SN1
reaction below?

CHEMISTRY SUBJECT TEST1

22. Which of the compounds below is an acid anhydride?

A.

CH2CH3
Br

ORGANIC

H+

H2O

O
?

CH3

O
B.

A.

CH2CH3
OH

OH

H
CH3

C.

B.

OH

CH2CH3
H

OH
D.

CH3

O
CH3CH2C

C.

CH2CH3
OH

CH2CH3

H and H
CH3

OH

OCH3
E.

O
CH3CH2C

CH3

O
O

CCH3

D.

CH2CH3
Br

23. Which of the following compounds will have the lowest

boiling point?

OH

A. CH3CH2CH2NH2
B. CH3CH2CH2COOH
C.

CH3
E.

CH2CH3
Br

OH and OH
CH3

NH2

CH2CH3
Br

CH3CHCH3
D. CH3CH2NHCH3
E. N(CH3)3

CH3
24. Which one of the compounds below is incapable of
significant hydrogen bonding?
A.
B.
C.
D.
E.

ethanol
bromoethane
propanoic acid
propanamide
ethanamine

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28. The IUPAC name for the compound below is
25. Which of the following statements is true of ethene?
A. Both carbon atoms are sp2 hybridized and the
molecule is planar.
B. Both carbon atoms are sp2 hybridized and all bond
angles are approximately 109.5.
C. One carbon atom is sp hybridized while the other is
sp2.
D. Both carbon atoms are sp3 hybridized and all bond
angles are approximately 109.5.
E. Both carbon atoms are sp hybridized and the
molecule is planar.
26. Which of the following depicts the most stable
resonance structure of diazomethane?

..

C N N:
H

B.

..

C N

CH3

CH3 CH2 CHCH2 CH2 CCH3

CH3
A.
B.
C.
D.
E.

2,2-dimethyl-5-ethylheptane.
5-ethyl-2,2-dimethylheptane.
3-ethyl-6,6-dimethylheptane.
6,6-dimethyl-3-ethylheptane.
Two of the above

29. Which of the following substrates is least reactive

towards SN2 reactions?
A.
B.
C.
D.
E.

A.

CH2 CH3

CH3I
CH3CH2Br
CH3CH2CH2I
(CH3)2CHCH2I
(CH3)2CHCH2Br

N:

H
C.

..

C N
.. N:
H

D.

..

C N
..

N:

H
E. They are all equally stable.
27. The compounds pictured below are

CH3
H

Br

Br

Br

Br

A.
B.
C.
D.
E.

CH3

CH3

CH3

enantiomers.
meso compounds.
diastereomers.
conformers.
configurational isomers.

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30. All of the following represent cis-1,4dimethylcyclohexane EXCEPT

ORGANIC

CHEMISTRY SUBJECT TEST1

A.

CH3
H

H3 C
H
B.

CH3
H

CH3
H

C.

H
H3 C

CH3
H

D.

H3 C

H3 C

E.

CH3
H3 C

STOP! END OF TEST.

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ORGANIC CHEMISTRY SUBJECT TEST 1

ANSWER KEY

1. D

7. B

13. A

19. D

25.A

2. A

8. D

14. C

20. E

26. B

3. B

9. B

15. A

21. C

27. B

4. A

10. C

16. C

22. E

28. B

5. D

11. E

17. A

23. E

29. E

6. A

12. D

18. A

24. B

30. C

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ORGANIC

CHEMISTRY SUBJECT TEST1

Explanations
1.

D
A trivalent carbon with an unpaired electron does not possess an octet and can hence be considered electron deficient.
The free radical, then, just like carbocations, is stabilized by the presence of groups which can share electrons inductively
(alkyl groups) or defuse the electron deficiency through resonance (conjugated systems). The order of free radical stability
goes 3>2>1>methyl. Allylic and benzylic radicals are similar to tertiary radicals in terms of stability because of resonance
delocalization. The free radicals shown in choice A (benzylic), choice B (tertiary), and choice E (allylic) are all relatively
stable, and therefore these three choices are incorrect. The radicals offered in choices C and D are both relatively unstable,
but the methyl radical depicted in choice D is more unstable than the primary radical in choice C. Thus choice D, as the most
unstable free radical, is the credited choice.

2.

A
Carbanions are stabilized either by electronegative substituent groups (absent in this case) or by resonance with _
electrons. Choices D and E do not allow for any resonance stabilization and will therefore be less stable than the other three
choices. The anion in choice A allows the negative charge to be delocalized, through resonance, over nine other carbon
atoms, three in each phenyl ring. Choices B and C allow for delocalization over six additional carbons and three additional
carbons, respectively. Choice A thus allows for the greatest amount of charge delocalization of any of the choices offered,
and is thus the most stable carbanion.

3.

B
The more energetically favorable a resonance structure is, the more it will contribute to the actual structure of the
hybrid. In other words, the actual electron density distribution of the hybrid molecule will more likely resemble the more
stable resonance structures. In looking for the resonance structure expected to make the least contribution, then, we are
looking for energetically unfavorable structures. It is highly unfavorable for electronegative species such as oxygen to bear a
formal positive charge, thus making B the correct choice. Choice A is the formal structural formula for acrolein. It is the most
stable of all the different resonance structures one can draw because there is no separation of charge. Choices C and D are
reasonable resonance forms which show how the conjugated double bonds delocalize the _ electrons and stabilize the
molecule: the electronegative oxygen bears a formal negative charge which is certainly acceptable.

4.

A
Questions on the physical properties of organic compounds are best answered based on general chemistry principles,
most notably those related to bond polarity and molecular interactions. Hydrogen bonding is the strongest intermolecular
force in which water can participate; alcohols also participate in hydrogen bonding, but this capability decreases with the
increasing size of the alkyl portion of the alcohol molecule, because the relatively nonpolar alkyl group disrupts the hydrogen
bonding network. Ethanol, choice A, has a smaller alkyl group than propanol, choice B. Ethanol thus has a greater capacity
for hydrogen bonding and will be more soluble in water than the propanol will be. Choices C and E show a ketone and an
ether respectively; these compounds are not as soluble in water since, even though they have polar carbon-oxygen bonds,
they have no hydrogens bonded to electronegative atoms that can contribute to hydrogen bonding. Choice D, an alkene, is the
least soluble in water of the choices offered.

5.

D
While this question is directly asking about the relative heats of hydrogenation of various polyenes, indirectly it is really
asking, "Which of the following has the most stable _ system?" Recall that conjugation lends special stability to compounds
with more than one _ bond. Thus the question could be further translated to "Which of the following has the most extensive
conjugated _ system?" Choice D is correct since 1,3,5-hexatriene has three double bonds in complete conjugation; it is thus
more stable than choice E, for instance, because the first two double bonds in the compound 1,2,4-hexatriene are cumulated,

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not conjugated. Choice A, 1,3-pentadiene, is conjugated but has only two _ bonds, choice B, 1,4-pentadiene, has two _ bonds
which are isolated, not conjugated, and choice C, 1,2-pentadiene, has two cumulated rather than conjugated _ bonds. Each of
these compounds is thus less stable per double bond than the 1,3,5-hexatriene of choice D.

6.

A
The reactant is a secondary alkyl halide; as such, it will react with iodide ions in an aprotic solvent via an SN2 pathway.
This fact is supported by the statement that the reaction proceeds with second order kinetics, the rate observation expected for
an SN2 reaction. Since SN2 reactions are accompanied by inversion of configuration, in most cases, it follows that if the
reactant is R, then the product will be S, vice versa. We must therefore next determine whether the reactant is R or S. It
would be most helpful to convert the Newman projection shown into a Fischer projection from which to determine the R/S
designation. The carbon in the background of the Newman projection shown has three hydrogens attached to it, so it is a
methyl group. Writing a Fischer projection for this compound then requires that we place the methyl group, the ethyl group,
the bromine atom, and the hydrogen atom (the four groups attached to the chiral carbon in the foreground of the Newman
projection) in the appropriate spatial order.

H
Br

CH2CH3

CH3

It should now be evident that the reactant is the R enantiomer of 2-bromobutane, and therefore the inverted product will
be the S enantiomer of 2-iodobutane, and choice A is confirmed as the correct answer.
7.

B
Amides are defined as organic compounds in which an amine functionality is directly bonded to a carbonyl carbon.
Choices A, C, and D are all simple amines (primary, secondary, and tertiary respectively); Choice E is a nitro compound,
which is an organic compound with an NO2 group. Only choice B has an amine group, N(CH3)2, bonded to a carbonyl
carbon.

8.

O O

O O
S

S
OH

H
N
H

H
H

O-

N
H

A zwitterion is a molecule that has both positive and negative charges. Usually amphoteric species, molecules that have
both acid and basic functional groups, can form zwitterions (e.g. amino acids). Sulfanilic acid has both an acid functional
group (SO3H) and a basic functional group (NH2), and can therefore have both a positive and negative charge
simultaneously (see diagram above of conjugate base and acid). Zwitterions have strong intermolecular attractions due to
ionic and hydrogen bonding, making D the correct choice. Any correct answer choice has to involve intermolecular
attractions, since that is what provides for high boiling points relative to molecular weight. No other answer choice addresses
intermolecular attractions, so can be eliminated. Additionally, all the other answer choices are stated incorrectly. The
10

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ORGANIC

CHEMISTRY SUBJECT TEST1

nitrogen of the amine group acts as a Lewis base (it has a free electron pair to donate), not a Lewis acid. Sulfanilic acid has
no chiral centers, so answer choices B and C can be eliminated. The sulfur atom is attached to three oxygens, so it must have
a very high oxidation state.

9.

B
Boiling requires that the molecules of a compound in the liquid phase overcome the intermolecular attractive forces and
escape into the gas phase: the stronger these interactions are, the more thermal energy one will have to put in to pull the
molecules apart, and hence the higher the boiling point. Choice E is obviously incorrect, as the alcohol will exhibit hydrogen
bonding, and will have a very high boiling point compared with similar compounds with no hydrogen bonding. Choices C
and D are incorrect because unsaturated compounds have an inherent (albeit small) dipole moment that raises their boiling
point compared with their saturated counterparts. When evaluating choices A and B, the rule to follow is that compounds
have a lower boiling point with increased branching, since branching disrupts the spatial packing of molecules in the
condensed phase and hence compromises intermolecular attractions. Choice B, the most branched of the saturated
compounds without hydrogen bonding, is the correct choice.

10.

C
All of the listed compounds are unsubstituted alkanes. Thus, the highest boiling point will belong to the longest, least
branched compound: the longer the alkane, the more it weighs and the more difficult it will be to push the molecule into the
gas phase. Also, longer alkanes experience stronger van der Waals forces. The two longest compounds are choices B and C,
each a five-carbon molecule. The highest boiling point belongs to the less branched alkane, in this case the straight chain
pentane, or choice C.

11.

E
Melting point is by and large dictated by the same characteristics that determine boiling point: intermolecular attraction,
weight, and geometry. In examining all of these compounds, only two have hydrogen bonding. Hydrogen bonding greatly
increases the interaction between molecules, giving them much higher melting points than similar compounds of similar size
without hydrogen bonding. Thus, choices D and E are likely candidates. Of the two, choice E is larger than choice D (a fivecarbon chain versus a three-carbon chain). So, choice E has the highest melting point.

12.

D
2-methoxy-3-butenal is a five carbon (but + meth) unsaturated (buten) aldehyde (butenal), or an alkene with a terminal
carbonyl group. This eliminates choices A and C, which are not aldehydes at all but ketones. Choice E is a six-carbon
molecule (pentenal with a methoxy group) and also is incorrect. In numbering the carbon atoms, the carbonyl carbon is
labeled carbon 1. This means that the methoxy group at carbon 2 must be next to the aldehyde carbon, with the double bond
starting at the next carbon (#3). This is the compound shown in choice D. Choice B is incorrect because it is 2-methoxy-2butenal.

13.

A
Cis and trans isomers are diastereomers with generally different physical properties, and so choice E can be eliminated.
The question comes down to which of the two isomers has the stronger intermolecular attractions. For the cis isomer, the
dipole moments of the two C-Cl bonds do not point directly opposite each other, and therefore the molecule will have a
permanent dipole moment when compared to the trans counterpart, in which the two dipole moments do cancel each other
vectorially. Choice A is thus correct because this asymmetry in the cis isomer leads to a net dipole moment, which in turn
gives the stronger intermolecular forces and higher boiling point.

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14.

C
Diastereomers are stereoisomers that are not mirror images of each other. Choice A is incorrect because only the
compound listed on the right is meso. Choice B is incorrect because enantiomers are mirror image isomers, which the two
compounds are not. This also eliminates choice E, because racemates are enantiomeric pairs. Choice D is obviously incorrect
because the two molecules, while similar, are not identical.

15.

A
SN1 reactions proceed through a carbocation intermediate, and are therefore dependent upon the quality of the leaving
group and the stability of the carbocation. In the compounds listed in choices AE, bromine is the leaving group. This leaves
only the stability of the carbocation intermediate to determine which compound is least likely to undergo an SN1 reaction.
Carbocation stability follows degree of substitution, i.e. 3>2>1>methyl. Since choice A, methyl bromide, will form the
least stable carbocation, it will be the least likely to undergo an SN1 reaction.

16.

C
The correct choice is C. Choice A is incorrect because while it is true that SN1 reactions proceed through a carbocation
intermediate, SN2 reactions never do: it is a single-step reaction that goes through a transition state instead of an intermediate.
Choice B is false because only the cation intermediate in SN1 reactions can undergo rearrangement to form a more stable
(more highly substituted) carbocation; SN2 reactions occur in one step and do not allow time for rearrangement to take place.
Choice C is a true statement because SN1 reactions favor substituted alkyl halides for the stable carbocations that they form,
whereas SN2 reactions favor unsubstituted reactants for their minimal steric hindrance. Choice D is incorrect from what we
just said: the exact opposite is true. Choice E is incorrect because SN2 reactions are favored by polar aprotic solvents which
cannot stabilize the (usually anionic) nucleophile, making it more reactive.

17.

A
The student should be able to eliminate Choices B and C immediately, as they have absolutely no hydrogen bonding.
Choices D and E are both terminal straight chain alcohols; thus the heavier compound (Choice D) has the higher melting
point of the two. This leaves choices A and D, compounds with similar chain length but different functional groups. Choice
A is correct because in addition to the hydroxyl group, it also has a polar carbonyl bond which serves to increase
intermolecular attractions.

18.

A
The correct choice is A. Choices C and D can be eliminated straight away because neither is an acid chloride.
Numbering of the four-carbon chain is simple. The first carbon is the carbonyl carbon. Proceeding down the carbon chain, the
double bond begins at the second carbon (2-buten), and the cyano group is on the third carbon (3-cyano). This is compound
A.

19.

D
A quick examination of the two compounds will reveal that they are non-superimposable mirror images, and therefore
enantiomeric. This eliminates choices A and B because diastereomers are stereoisomers that are not mirror images. Of
choices C and D, C is incorrect because the physical properties of enantiomers are identical. Choice E is incorrect because
meso structures possess a plane of symmetry and are hence achiral.

20.

12

E
The two compounds are actually identical compounds, and correspond to a meso structure since it has two chiral centers
but nonetheless possesses a plane of symmetry. Meso compounds are all optically inactive, and therefore choice D cannot be
true.
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21.

ORGANIC

CHEMISTRY SUBJECT TEST1

C
This answer is easily obtainable if two criteria for this reaction can be remembered. First, SN1 reactions proceed through
a planar intermediate in which the central carbon atom is sp2 hybridized. This means that the nucleophile can attack from
above or below the plane of the cation, yielding a racemic mixture of compounds. Since we started with an optically active
compound, the correct choice will have two compounds listed that differ in the configuration around one carbon atom. This
eliminates choices A, B, and D. Secondly, the bromide ion is the obvious leaving group (stable in water, or will form HBr in
an organic solvent in the presence of the H+ ion), so the compounds listed in the correct choice will not include a bromide
ion. This eliminates choice E. Therefore, choice C is the correct answer.

22.

E
Acid anhydrides are two acid molecules that are linked with an ester-like bond with the loss of water. They are very
reactive, and will regenerate the acids used to form them when water is added. This relationship for the acid anhydride in
question can easily be visualized as follows:

O
CH3CH2C

+
OH

HO

-H2O

CCH3

+H2O

O
CH3CH2C

O
O

CCH3

Choice A is a diketone. Choice B is an a-keto alcohol. Choice C is phenol. Choice D is an ester.

23.

E
Since we are looking for the lowest boiling point, we should look for compounds in which there is little or no hydrogen
bonding. All the choices except for choice E possess hydrogens bonded to an electronegative atom (O or N in this case):
choice B is a carboxylic acid which, in addition to the capacity for hydrogen-bonding, also possesses a polar carbonyl bond
which increases its boiling point. Choices A and C are primary amines, each with two hydrogen atoms directly bonded to
nitrogen. Choice D is a secondary amine with one hydrogen capable of hydrogen bonding. Compound E, however, is a
tertiary amine, which means that the nitrogen atom does not directly bond to a hydrogen atom. This lack of possibility for
hydrogen bonding translates into the lowest boiling point of the five.

24.

B
Hydrogen bonding is only found in compounds where a hydrogen atom is bonded to a very electronegative atom, such
as oxygen, fluorine, or nitrogen. It is readily apparent that the only compound where a hydrogen atom is not bound to an
electronegative atom is choice B, where all of the hydrogens are bound to carbon atoms.

25.

A
The two carbon atoms in ethene are bonded to each other via a double bond. They are thus both sp2 hybridized and the
three attached groups each has will be arranged in a planar configuration roughly 120_ apart, since that will minimize the
electron-pair repulsion. Choice B is wrong because of the bond angle. The other choices are wrong because both carbons are
sp2 hybridized; sp hybridization is found on carbon atoms with two double bonds (allenes) or, more commonly, a triple bond
and a single bond (alkynes), while sp3 hybridization is found on saturated carbon atoms.

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26.

B
Choice B is the only resonance structure shown in which both nitrogen atoms and the carbon atom have an octet of
valence electrons. Choice A is incorrect because it shows the carbon atom with 10 valence electrons. One may argue that it
does not even constitute a valid resonance structure. The carbon atom in the structure shown in choice C only has 6 valence
electrons, and will therefore not be as stable as B. Choice D is also not as stable because the nitrogen atom on the end only
has 6 valence electrons. It also involves more charge separation than choice B.

27.

B
The two structures shown actually represent the same compound. It is a meso structure because it has a plane of
symmetry while possessing two chiral centers. Choice A is incorrect because enantiomers are mirror images that are not
superimposable upon each other; the two compounds are mirror images of each other but are superimposable (identical).
Choice C is incorrect because diastereomers are stereoisomers (isomers that differ only in the way their atoms are arranged in
space) that are not mirror images and likely to exhibit different physical and chemical properties. Choices D and E are
incorrect because conformers or conformational isomers are compounds that differ only in rotation around one or more single
bonds, and are essentially different rotated or bent shapes of the same molecule.

28.

B
Choice E is incorrect because any given organic compound has only one IUPAC name (with the exception of certain
common names that are recognized by the IUPAC). The first rule is to find the longest carbon chain, which is 7, making this
a heptane (no multiple bonds or non-alkyl side groups). Then, the side chains (two methyl on the same carbon and one ethyl
on another) are named, and their positions numbered to yield the lowest set of numbers is given for the side chains (2 and 5,
respectively). Add prefixes to show how many side chains there are (ethyl and dimethyl), and alphabetize (not counting the
prefix). The compound is 5-ethyl-2,2-dimethylheptane.

29.

E
SN2 reactions are inhibited by bulky, branched side chains and favored by good leaving groups. Choice A, iodomethane
(methyl iodide), is the most unhindered and equipped with a good leaving group: the iodide ion. It will therefore react readily
via the SN2 mechanism. Straight chain alkyl halides such as choices B and C are also likely to undergo SN2 type reactions
because they are primary, straight chain (unhindered) alkyl hydrocarbons. Of choices D and E, neither is a very good
candidate for an SN2 reaction because even though they are still primary halides, they are branched and therefore slightly
more sterically hindered relative to the other choices. The only difference between these two choices is the nature of the
halogen which will act as the leaving group in its ionic form. Therefore, the choice for the worst SN2 reactivity would be
choice E, which has the worse leaving group: bromide rather than iodide ion.

30.

C
Cis compounds are compounds in which the substituents (methyl groups in this case) are on the same side of the
molecule in question. It should be obvious that D and E are incorrect because the methyl groups are on the same side of the
cyclohexane ring in both species. In choices A and B, the structures drawn depict one methyl group in the axial and one
methyl group in the equatorial position; they are both on the same side of the molecule relative to the other substituents (the
hydrogen atoms). Only in the compound shown in choice C are both methyl groups equatorial, and on opposite sides of the
molecule (trans). Note that this molecule would still be trans if both methyl groups had been portrayed in the axial position.

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