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Mock GAMSAT exam - Chemistry 2015/2016 Course

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This exam booklet consists of 35 questions.

Circle the correct answer in a black or blue pen.


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Questions 1-5

Substitution reactions are defined as a displacement reaction where a functional group of one chemical
compound is replaced by another group of a second compound. Nucleophilic substitution reactions are an
important class of organic reactions that involve a molecule that can donate a pair of electrons. The general
reaction scheme is shown below:

There are two main mechanisms in substitution reactions of alkyl halides, namely the unimolecular
substitution (SN1) and bimolecular substitution (SN2) mechanisms. Below are reaction schemes that illustrate
the difference between the two mechanisms.

Unimolecular substitution (SN1)

Bimolecular substitution (SN2)


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Below are general rules that govern whether a substitution reaction between an alkyl halide and a nucleophile
undergoes SN1 or SN2 mechanism:

1. The SN1 mechanism dominates when the reaction site is crowded due to steric effects.
2. Tertiary alkyl halides can only undergo substitution reaction via the SN1 mechanism.
3. The SN2 mechanism requires the presence of a nucleophile.
4. The SN2 mechanism is not favoured in the presence of a strong base as a nucleophile.
5. Primary alkyl halides can only undergo substitution reactions via the SN2 mechanism.
6. Secondary alkyl halides can undergo either SN1 or SN2 mechanism, and strongly depends on the
crowding at the reaction site of the alkyl halide.

1 The order of a reaction describes the dependence of the rate of the reaction on the reagents. A
reaction with order n is dependent on the concentration of n reagents. Typically the order of the
reaction is defined by the rate-determining step for that reaction. The SN1 and SN2 mechanisms are,
respectively,

A Both first order reactions


B Both second order reactions
C First order, and second order reactions
D Second order, and first order reactions

2 For tertiary alkyl halides, only the SN1 mechanism dominates because

A The nucleophile in SN1 mechanisms is a strong base


B The carbocation thats formed as an intermediate is not stable
C The nucleophile cannot reach the reactive site
D The functional groups attached to the reactive site are inert

3 Which of the following will most likely undergo substitution reaction with water as the nucleophile via
the SN1 mechanism?

A Tert-butanol
B 2,2-dichloropropane
C 3,3,3-trifluoro-1-chloropropane
D 2-chloro-2,5-dimethyl-6-cyclobutylhexane

4 In a substitution reaction involving (R)-3-bromo-2,2,3-trimethylpentane and water via the SN1


mechanism, the stereochemistry of the product will be:

A Preserved
B Inverted
C Racemic
D Cannot be determined

5 Using a strong base, the most likely product for a reaction of aqueous tert-butylchloride and its
respective mechanism is:

A tert-butanol, SN1
B tert-butanol, SN2
C 2-methyl-1-propene, SN1
D 2-methyl-1-propene, SN2
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Questions 6-9
Alcohol groups can be oxidized to aldehydes or ketones, and aldehydes can be further oxidized to carboxylic
acids, whereby the hydrogen that was bonded to the carbonyl carbon of the aldehyde is replace by an -OH
group. Ketone groups are fully oxidized and the presence of an oxidizing agent will not result in any reaction.
Because ketones cannot be oxidized, treatment of a substance with an oxidizing agent is a simple chemical
technique that can be used to distinguish between aldehydes an ketones. Two such oxidizing agents are
Tollens' reagent and Benedict's reagent.

Tollens' reagent consists of silver ions (Ag+) in aqueous ammonia, giving [Ag(NH3)2]+ ions as the colorless
oxidizing agent, and produces metallic Ag when reduced. Benedict's reagent contains blue copper(II) ions
which can be reduced to red copper(I) oxide.

Both reagents selectively oxidise aldehyde groups only, with one exception. Tollens reagent is more specific
than Benedict's reagent in that the latter will also react with ketones that have an alcohol group on a carbon
next to the ketone carbon (chemicals called -hydroxy ketones), oxidizing the alcohol group to an aldehyde or
ketone group as appropriate.

Consider the four chemicals below:

6 Which of the four chemicals would reaction with Tollens' reagent?


A B and C
B B
C B, C and D
D B and D

7 Tollens' reagent and Benedict's reagent would both need to be used in order to completely distinguish
between which chemicals?
A A, B and C
B B and D
C A and C
D A, B and D

8 If both Tollens' reagent and Benedict's reagent were added to a solution containing excess chemical A,
how could the resulting solution be described?
A A blue solution containing diamino silver ions.
B A blue solution containing a solid metal precipitate.
C A red solution containing diamino silver ions.
D A red solution containing a solid metal precipitate.

9 If all four chemicals were mixed and then completely reacted with excess Tollens' reagent and
Benedict's reagent, which of the following statements would be true of the resulting solution?
A Two of its chemical constituents would have a single carboxylic acid group and the other two would
have a single ketone group.
B Two of its chemical constituents would have a single carboxylic acid group and one would have two
ketone groups.
C It would contain a chemical constituent with two carboxylic acid groups, another constituent with a
single ketone group, and two more constituents with single carboxylic acid groups.
D It would contain two chemical constituents with single ketone groups and another two with single
carboxylic acid groups.
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Questions 10-11

Based on the VSEPR theory, electron pairs are involved in bonding. Bonding structures with a simple AB n
geometry are arranged in the following way. This occurs because electron pairs repel eachother to give the
maximum possible bond angle between groups.

Electron Bonding pairs Lone pairs Shape Bond angle


Arrangement
Linear n/a n/a Linear 180
Trigonal planar 3 0 Trigonal planar 120
2 1 Bent 120
Tetrahedral 4 0 Tetrahedral 109.5
3 1 Trigonal pyramidal 107
2 2 Bent 104

10 Nitrogen has 5 valence electrons which can participate in binding. Hydrogen is bund to nitrogen in
ammonia (NH3) by single covalent bonds.

What is the bond angle of ammonia?

A 180
B 120
C 109.5
D 107

11 Given sulfur has 6 valence electrons, what is the bond angle of SF 6?

A 90
B 104
C 107
D 120
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Questions 12-14

The above phase diagram describes the phase changes of water.

12 Phases A, B and C represent, respectively:

A Liquid, solid, gas


B Solid, liquid, gas
C Gas, liquid, solid
D Gas, solid, liquid

13 What form does water take at 0.1 C and 0.5 kPa?

A Solid
B Liquid
C Gas
D Cannot be determined

14 Point D is the triple point, where all three phases of water exist simultaneously. If a slight increase in
pressure occurs from this point, what phase would water take?

A Solid
B Liquid
C Gas
D Cannot be determined
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Questions 15 18

The Fischer projection is a 2D representation of 3D molecules. It is drawn by considering what


the molecule would look like when viewed from a given angle, to give horizontal and vertical lines as below.

15 Which of the following Fischer projections depict the following organic molecule correctly?

16 Which of the following statements is true?


A Mirroring a Fischer projection along a vertical plane results in the same stereoisomer.
B Mirroring a Fischer projection along a horizontal plane results in the same stereoisomer.
C Rotating a Fischer projection 90 degrees results in the same stereoisomer
D Rotating a Fischer projection 180 degrees results in the same stereoisomer

17 Three of the four Fischer projections below belong to the same stereoisomer. Which is the odd one out?

A I
B II
C III
D IV

18 Consider the two organic compounds 2-pentanol and 2,2-dichloro-1,1-dibromopentane. Stereoisomers


are possible for
A Both molecules
B 2-pentanol but not 2,2-dichloro-1,1-dibromopentane
C 2,2-dichloro-1,1-dibromopentane but not 2-pentanol
D Neither 2-pentanol nor 2,2-dichloro-1,1-dibromopentane
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Questions 19-23

An amide bond is a functional group that is commonly found in biological molecules such as DNA, which
consists of a carbonyl group and an amine group, as shown below:

The amide functional group

The IUPAC rules of naming an amide are similar to that of alkanes, with the exception of the following rules:
1. The molecule is first considered as two halves, one consisting of the carbonyl group, and the other the
amine group.
2. The half that consists of the carbonyl group forms the last half of the name by replacing e with amide.
3. The half that consists of the amine group will form the front half of the name, where the substituent
group is connected to the nitrogen of the amine group, and has a prefix of N-

19 What is the name of the following molecule?

A 1,1-bromochlorobutanamide
B N,N-bromochloropropanamide
C N-bromochlorobutanamide
D N-bromo-N-chlorobutanamide

20 Which of the following is the molecule: N-isopentyl-N-isopropylbutanamide?


(Hint: iso- indicates the presence of a tertiary hydrocarbon group)

A
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The amide group can be synthesized by a reaction between an acyl chloride and an amine:
O O

+ H2 N
Cl N
H

Pentanoyl Chloride Ethylamine X


21 What is the name of the amide thus produced?
A N-pentylethanamide.
B N-butylethanamide
C N-ethylbutanamide
D N-ethylpentanamide

This amide synthesis is also known as acylation, where the acid chloride group is typically generated through
the use of thionyl chloride in the following reaction:

Using this reaction, a student attempts to graft acyl chloride groups onto the surface of carbon nanotubes. A
carbon nanotube is an allotrope of carbon with a cylindrical structure. Its made up of carbon atoms organized
in a continuous hexagonal orientation, essentially a sheet of aromatic rings, rolled up into a tube.
He finds that the reaction was not successful after several attempts and uses IR-spectroscopy to identify the
potential problem. Below are IR-spectra of (left) pure carbon nanotubes and (right) what was used in the
reaction. Functional groups are assigned to each of the observed peaks.

22 Which functional group did this student hope to find on his nanotubes for the above reaction?
A Alcohol.
B Ketone
C Carboxylic acid
D Aldehyde

23 What was the issue with reactivity of the carbon nanotubes according to the IR-spectra?
A The nanotubes were not dispersed evenly, therefore reactive sites were not accessible.
B Due to pi-pi stacking between carbon nanotubes, the reactive sites are sterically hindered
C There is a lack of carboxylic acid groups on the surface of the carbon nanotubes.
D Cannot be determined, further analysis using Mass Spectrometry is needed to confirm the structure of
the carbon nanotubes.
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Questions 24-29
Optical polarimetry is an important analytical technique best used for differentiating between mirror images
of optically active chemical compounds. It relies on measuring the optical rotation of light passed through a
solution of the sample with known concentration. This can then be related to the specific rotation for the
compound using the formula
[] = /cl
where [] is the specific rotation of the compound, is the measured rotation, c is the concentration of the
solution in g/mL and l is the optical path length in cm. The specific rotation of a compound can be positive or
negative; if the specific rotation of a compound is known, the specific rotation of its mirror image will be equal
in magnitude but opposite in sign.

24 Optical polarimetry is best used for differentiating between what type of isomers?
A Constitutional isomers
B Geometric isomers
C Conformational isomers
D Enantiomers

25 A sample of an unknown organic compound with concentration 0.2 g/mL is found to have an optical
rotation of +11.4 when measured in a polarimeter with a 2 cm path length. What is the specific
rotation of this compound?
A +4.6
B +11.4
C +28.5
D +57

26 If the rotation of the same compound is measured using a 0.4 g/mL solution, which of the following
changes will occur?
A The optical rotation of the solution will increase
B The optical rotation of the solution will decrease
C The specific rotation of the solution will increase
D The specific rotation of the solution will decrease

27 The specific rotation of (R)-2-bromobutane is -23.1. What will be the measured optical rotation of a
solution of (S)-2-bromobutane with concentration 0.3 g/L and a path length of 1 cm?
A +6.93
B -6.93
C +77
D -77

Optical polarimetry can also be used to estimate the enantiomeric excess (ee) of a mixture of two
enantiomers, if the specific rotation of one enantiomer is known. The enantiomeric excess reflects the degree
to which a sample contains one enantiomer in greater amounts than the other; a sample with 70% of one
enantiomer and 30% of the other has an ee of 40% of the first enantiomer.

If [] is the specific rotation of one isomer, and the measured rotation of a 1 g/mL mixed solution of both
enantiomers with path length 1 cm is , then the enantiomeric excess is

ee = /[]
28 A chemist prepares a batch of 2-bromobutane with unknown enantiomeric purity. A solution is
prepared from this batch with a concentration of 1 g/mL and the rotation is measured to be -9.2
through a path length of 1 cm. What approximate percentage of the batch is (R)-2-bromobutane?
A 30%
B 40%
C 60%
D 70%
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29 If a solution made from another batch of 2-bromobutane is similarly prepared and the rotation is found
to be +9.2, what approximate percentage of the batch is (R)-2-bromobutane?
A 30%
B 40%
C 60%
D 70%

Questions 30-31
A common set of organometallic reagents are the Grignard reagents, which have an organic component bound
to MgX, with the X being a halide ion to balance the charge. They are commonly reacted with carbonyl
compounds as below.

30 What Grignard reagent would be reacted with formaldehyde (H2CO) to form 1-propanol?

A There is no Grignard reagent that can undergo this reaction

31 What pair of reagents would undergo a Grignard reaction to form the alcohol below?

A A B

C D
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Questions 32-35
Effusion is the process of gas molecules escaping from a small hole in a container. Effusion obviously depends
on the size of the hole. If small enough, effusion may not occur because, like a beach ball hitting a basketball
hoop, the molecules can't fit. Larger holes obviously allow molecules to escape faster. If the hole is large
enough, the process may be considered diffusion instead of effusion. Graham's Law can be used to
approximate the ratio of effusion rates between two gases of different molecular weights. The more massive a
gas is, the slower it effuses.
1 2
=
2 1

32 Gas X effuses through a pinhole at a rate of 4 x 10-4 mol s-1. Methane effuses through the same pinhole at
a rate of 2 x 10-4 mol s-1 under the same conditions of temperature and pressure. What is the likely
identity of gas X?
A Hydrogen
B Helium
C Oxygen
D Sulfur

33 1 mole of helium gas is allowed to equilibrate with 1 mole of nitrogen gas on the left hand side of a
container separated by a divider as shown below. A hole is poked in the divider big enough for both
helium and nitrogen to pass through. After a short amount of time has passed, what is the ratio of
helium to nitrogen molecules on the right hand side?

A 1/7
B 1/14
C 7
D 14

34 The container is left with the hole in the divider for a very long period of time. What is the ratio of
helium to nitrogen molecules on the right hand side?
A 1
B 2
C 7
D 14

35 Effusion can be seen with balloons. Effusion proves that the balloon has holes in it, even though it looks
totally impassable. When left alone for several days, a balloon filled with helium will eventually deflate.
If a balloon was filled with hydrogen gas (H2), it would deflate:
A at the same rate, as the holes are only large enough for one molecule of gas at a time
B more slowly, as the effective width of diatomic hydrogen is more than that of helium
C at the same rate, as they have the same molecular weight (MW = 2)
D more quickly

END OF MOCK EXAM