Fundamentals of Organic Chemistry 7Th International Edition by MCMURRY – Test Bank
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Sample Test
Chapter 3 – Alkenes and Alkynes: The Nature of Organic
Reactions
Instructions: Classify each reaction below
as a(n):
|
a. |
addition |
|
b. |
elimination |
|
c. |
substitution |
|
d. |
rearrangement |
1.
ANS: C
2.
ANS: D
3.
ANS: A
4. Which
of the following is a characteristic of a polar reaction?
|
a. |
symmetrical bond making and breaking |
|
b. |
one electron from each reactant forms
the bond |
|
c. |
involves a neutral species with an
unpaired electron |
|
d. |
are more common that radical reactions |
|
e. |
all of these |
ANS: D
5. In an
organic reaction, which of the following is most likely to function as only a nucleophile?
|
a. |
BF3 |
|
b. |
(CH3)2CH2NH2 |
|
c. |
Fe2+ |
|
d. |
CH3CH2S– |
|
e. |
both a and c |
ANS: D
Instructions: Identify the functional
groups present in each compound below, and predict the direction of polarity in
each.
6. Identify
and predict:
mustard gas Cl-CH2CH2-S-CH2CH2-Cl
ANS:
7. Identify
and predict:
|
amphetamine |
ANS:
Instructions: Classify each structure below
as a nucleophile or electrophile, and briefly explain your choice.
8. Classify
and explain:
|
azide |
ANS:
Azide ion is a nucleophile because it has a net negative charge
(and lots of nonbonding electron electron pairs!).
9. Classify
and explain:
|
phenol |
ANS: Phenol can be a nucleophile or an electrophile
Instructions: Identify and label the
nucleophile and electrophile in each reaction below.
10.
Identify and label:
ANS:
11.
Identify and label:
ANS:
Instructions: Add curved arrows to the
following reaction(s) to indicate the flow of electrons in each.
12.
Indicate flow:
ANS:
13.
Indicate flow:
ANS:
Instructions: The reaction below is
commonly used as a laboratory preparation of cyclohexene. Use this reaction to
answer the following question(s).
14.
Refer to instructions. The forward and reverse reactions are
classified, respectively, as:
|
a. |
addition, elimination |
|
b. |
elimination, substitution |
|
c. |
elimination, addition |
|
d. |
elimination, rearrangement |
|
e. |
substitution, addition |
ANS: C
Instructions: Match each definition to one
of the terms below.
|
a. |
polarization |
|
b. |
addition reaction |
|
c. |
radical reaction |
|
d. |
electrophile |
|
e. |
polar reaction |
|
f. |
substitution |
|
g. |
nucleophile |
|
h. |
elimination reaction |
15.
A reaction that involves a species with an unpaired electron.
ANS: C
16.
Another term used for a Lewis acid.
ANS: D
Instructions: Match each definition to one
of the terms below.
|
a. |
transition state |
|
b. |
endergonic reaction |
|
c. |
activation energy |
|
d. |
Gibbs free energy change |
|
e. |
exergonic reaction |
|
f. |
reaction intermediate |
17.
A species that lies at an energy maximum during an individual
step in a reaction.
ANS: A
18.
The energy needed by reactants to reach the transition state.
ANS: C
Instructions: Consider the reaction of
2-bromo-2-methylpropane with water, shown below, to answer the following
question(s).
19.
Refer to instructions. This reaction is an example of:
|
a. |
a substitution reaction. |
|
b. |
a rearrangement reaction. |
|
c. |
an elimination reaction. |
|
d. |
an addition reaction. |
ANS: A
Instructions: In the reaction below:
|
a) |
Label the nucleophile (Nu) and the
electrophile (E). |
|
b) |
Draw arrows on the structures showing
electron flow in the reaction. |
20.
Label and indicate flow:
ANS:
Instructions: Use the reaction energy
diagram below to answer the following question(s).
21.
The transition state is found at _____ on the diagram.
ANS: B
22.
The products are found at _____ on the diagram.
ANS: D
23.
The free-energy change for the reaction is indicated at _____ on
the diagram.
ANS: C
24.
The reactants are found at _____ on the diagram.
ANS: A
25.
The following group is a substituent on a molecule. What is an
accepted IUPAC name for this group?
|
a. |
propenyl |
|
b. |
allyl |
|
c. |
vinyl |
|
d. |
propylene |
|
e. |
either a or b |
ANS: E
26.
What is the IUPAC name of the following compound?
|
a. |
(E)-3-methylpent-3-ene |
|
b. |
(Z)-3-methylpent-3-ene |
|
c. |
(E)-3-methylpent-2-ene |
|
d. |
(Z)-3-methylpent-2-ene |
ANS: D
27.
Name this compound.
ANS:
1-ethynyl-2-methylcyclopentane
28.
Choose substituents X and Y (listed in order below) for the
following compound so as to make a Z isomer.
|
a. |
-Br, -NHCH3 |
|
b. |
-F, -CHO |
|
c. |
-I, -OCH3 |
|
d. |
-COOH, -CH2NH2 |
|
e. |
-Br, -COOH |
ANS: B
Instructions: Draw structures corresponding
to each name below.
29.
Draw:
(3E)-3,7-dimethylocta-1,3,6-triene
ANS:
30.
Draw:
trans-4,4-dimethylpent-2-ene
ANS:
Instructions: Pent-2-ene is an example of
a disubstituted alkene.
Use this alkene to answer the following question(s).
31.
Refer to instructions. Draw the cis and trans isomers of
pent-2-ene and label them.
ANS:
|
cis |
trans |
32.
Refer to instructions. Circle the
isomer of pent-2-ene that is most stable.
ANS:
Instructions: Provide names for each
structure below. Be sure to include the cis,trans or E,Z designations
where applicable.
33.
Name and designate:
ANS:
trans-2-methylhex-3-ene or (E)-2-methylhex-3-ene
34.
Name and designate:
ANS:
3-methylcyclopentene
35.
Name and designate:
ANS:
cis-3,3-dimethyl-4-propylocta-1,5-diene or (Z)-3,3-dimethyl-4-propylocta-1,5-diene
36.
Rank each set of substituents using the Cahn-Ingold-Prelog
sequence rules by numbering the highest priority substituent 1 and numbering
the lowest priority substituent 4. Place the number in the blank below the
substituent.
ANS:
37.
Which of the following substituents has the highest priority
according to the Cahn-Ingold-Prelog system?
|
a. |
-COOH |
|
b. |
-CHO |
|
c. |
-CH2OH |
|
d. |
-CH3 |
ANS: A
38.
Which of the following substituents has the highest priority
according to the Cahn-Ingold-Prelog system?
|
a. |
-NH2 |
|
b. |
-NHCH3 |
|
c. |
-CH2NH2 |
|
d. |
-CH2NHCH3 |
ANS: B
Instructions: Assign E or Z configurations to
each alkene below.
39.
Assign:
ANS: Z
40.
Assign:
ANS: E
41.
The structures below show the stepwise bond making and bond
breaking in this reaction. Draw curved arrows to show the electron flow that
has occurred in each step.
ANS:
42.
Predict the product of the following reaction of Prostaglandin H2 by
interpreting the flow of electrons as indicated by the curved arrows.
ANS:
43.
Below are all the chemical structures and intermediates involved
in a reaction. On the structures provided, show all electron flow using the
arrow formalism for the complete stepwise mechanism.
ANS:
Chapter 5 – Aromatic Compounds
1. What
is the IUPAC name of the following compound?
|
a. |
2,4-dibromotoluene |
|
b. |
2,4-dibromophenol |
|
c. |
2,4-dibromoaniline |
|
d. |
4,6-dibromophenol |
ANS: B
2. What
is the IUPAC name of the following compound?
|
a. |
3-bromo-4-nitrobenzaldehyde |
|
b. |
2-bromo-1-nitro-4-benzoic acid |
|
c. |
3-bromo-4-nitroacetophenone |
|
d. |
3-bromo-4-nitrobenzoic acid |
ANS: D
3. Which
of the following compounds is aromatic?
|
a. |
ethane |
|
b. |
cyclobuta-1,3-diene |
|
c. |
benzene |
|
d. |
cycloocta-1,3,5,7-tetraene |
ANS: C
4. What
is the major organic product obtained from the following reaction?
|
a. |
|
c. |
|
|
b. |
|
d. |
|
ANS: C
5. Which
of the following undergoes the most rapid bromination upon treatment with Br2/FeBr3?
|
a. |
benzene |
|
b. |
nitrobenzene |
|
c. |
bromobenzene |
|
d. |
benzaldehyde |
ANS: A
6. Which
of the following undergoes the most rapid acylation upon treatment with acetyl
chloride and AlCl3?
|
a. |
benzene |
|
b. |
toluene |
|
c. |
chlorobenzene |
|
d. |
1,4-dichlorobenzene |
ANS: B
7. Which
of the following sets of substituents are all o/p-directing in electrophilic
aromatic substitution reactions?
|
a. |
Cl, CH3, CN |
|
b. |
Br, OH, COCH3 |
|
c. |
Cl, OH, CH3 |
|
d. |
CN, NO2, COCH3 |
ANS: C
8. Which
of the following sets of substituents are all deactivating groups in electrophilic
aromatic substitution reactions?
|
a. |
Cl, CN, NO2 |
|
b. |
Cl, NH2, CH3 |
|
c. |
CH3, OCH3, COCH3 |
|
d. |
CH3, NH2, OCH3 |
ANS: A
9. What
is the major organic product obtained from the following reaction?
|
a. |
|
c. |
|
|
b. |
|
d. |
|
ANS: A
10.
An accurate description of the structure of benzene is:
|
a. |
The p bonds are quickly moving around
the ring. |
|
b. |
There are two distinct structures that
are in equilibrium. |
|
c. |
All the carbon-carbon bonds are equal
in length. |
|
d. |
There are distinct single and double
bonds. |
|
e. |
Some bonds are longer than others. |
ANS: C
11.
Which of the following is a correct statement regarding
electrophilic aromatic substitution?
|
a. |
The carbocation intermediate will lose
a proton to regain aromaticity, usually from a position other than the site
of electrophilic attack. |
|
b. |
Formation of the carbocation
intermediate has a high activation barrier due to loss of aromaticity. |
|
c. |
The carbocation intermediate has
several resonance structures and is negatively charged. |
|
d. |
Re-formation of the aromatic ring has a
low activation barrier and therefore occurs slowly. |
|
e. |
Many suitable electrophiles are
unreactive and can be stored for long periods of time prior to use. |
ANS: B
12.
Place the following in order of reactivity towards electrophilic
aromatic substitution.
|
a. |
I > II > III > IV |
|
b. |
I > II > IV > III |
|
c. |
II > I > III > IV |
|
d. |
II > I > IV > III |
|
e. |
III > IV > II > I |
ANS: B
13.
What is the correct assignment of the names of the following
aromatic compounds?
|
a. |
1 = anisole; 2 = furan; 3 = pyrimidine |
|
b. |
1 = aniline; 2 = pyrrole; 3 = pyridine |
|
c. |
1 = anisole; 2 = pyridine; 3 = pyrrole |
|
d. |
1 = aniline; 2 = imidazole; 3 =
pyridine |
ANS: B
14.
Draw the structure of 4-bromo-2-fluorotoluene.
ANS:
15.
Draw the resonance structures for acenaphthene.
ANS:
16.
Circle the compound(s) in the following set that will undergo
both substitution and addition when treated with Br2.
ANS:
17.
Consider the production of 1-bromo-4-nitrobenzene:
|
a) |
Explain why Pathway A for the
production of 1-bromo-4-nitrobenzene produces a higher yield of the product. |
|
|
|
|
b) |
If reaction Pathway A is carried out at
high temperatures, a trisubstituted product forms. Draw the structure of the
product and explain why it forms. |
ANS:
|
a) |
Bromine is an o/p-director while the
nitro group is a meta director. |
|
|
|
|
b) |
|
|
|
|
|
|
Bromine is an o/p-director while the
nitro group is a meta director. Both groups direct the second -NO2 to the same
position–the position that is ortho to -Br and is also meta to -NO2. |
18.
Consider the following sequence of reactions:
|
a) |
What is the major organic product
obtained from the sequence of reactions? |
|||
|
|
a. |
b. |
c. |
d. |
|
|
|
|||
|
b) |
If KMnO4 had been replaced by
Na2Cr2O7, what would be the final
product of the reaction? |
|||
ANS:
|
a) |
c |
|
|
|
|
b) |
No change, the product would still be
the oxidation of the alkyl side chain. |
19.
Draw the major product of the following reaction:
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