Fundamentals of Organic Chemistry 7th Edition By John E. 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:
ANS:
20.
Consider the following compound:
|
a) |
Provide the correct IUPAC name for the
compound. |
|
|
|
|
b) |
Draw and name the other isomeric nitrotoluenes. |
ANS:
|
a) |
m-nitrotoluene or 1-methyl-3-nitrobenzene |
||
|
|
|
||
|
b) |
p-nitrotoluene |
o-nitrotoluene |
|
|
|
1,4-nitrotoluene |
1,2-nitrotoluene |
|
|
|
|
||
Instructions: Consider the reaction below
to answer the following question(s).
21.
Refer to instructions. The nucleophile in the reaction is
indicated by letter _____.
ANS: A
22.
Refer to instructions. The Lewis acid catalyst in the reaction
is indicated by letter _____.
ANS: C
23.
Refer to instructions. This reaction proceeds _____________ (faster
or slower) than benzene.
ANS: slower
24.
Refer to instructions. Draw the structure of product D.
ANS:
25.
Which of the following heterocycles is aromatic?
|
a. |
|
|
b. |
|
|
c. |
|
|
d. |
|
ANS: A, B, D
26.
Circle the aromatic portion of the following molecule:
ANS:
27.
Circle the aromatic portion of the following molecule:
ANS:
28.
Draw the structure of m-fluoronitrobenzene.
ANS:
29.
Draw the structure of p-bromoaniline.
ANS:
30.
Draw the structure of o-hydroxybenzoic
acid.
ANS:
31.
Draw the structure of 3,5-dimethylphenol.
ANS:
32.
Draw the structure of p-chlorobenzaldehyde.
ANS:
Instructions: Provide the IUPAC name
for each of the following compounds.
33.
IUPAC Name:
ANS: m-nitrotoluene
34.
IUPAC Name:
ANS: isopropylbenzene or cumene
35.
IUPAC Name:
ANS: cis-1-methyl-3-phenylcyclohexane
36.
IUPAC Name:
ANS: 2,4-diaminotoluene
37.
IUPAC Name:
ANS:
(E)-2,3-diphenyl-2-butene
Instructions:
Consider the Friedel-Crafts alkylation reaction below to answer
the following questions:
38.
Draw the structure of the electrophile in this reaction.
ANS:
39.
What is the role of the AlCl3 in
the reaction?
ANS:
The AlCl3 is a Lewis
acid catalyst that assists in the ionization of the alkyl halide to give the
carbocation electrophile.
40.
On the structures provided below, draw arrows showing the
complete stepwise mechanism for this reaction.
ANS:
Instructions:
Given the major organic product(s) of each of the following
reactions. If no reaction is predicted, write “N.R.”
41.
Write the product:
ANS:
42.
Write the product:
ANS:
43.
Write the product:
ANS:
44.
Write the product:
ANS:
45.
Write the product:
ANS:
46.
Write the product:
ANS:
47.
Write the product:
ANS:
48.
Write the product:
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