Multiple Choice Quiz

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1
Classify the reaction shown below as an electrocyclic reaction, cycloaddition, sigmatropic rearrangement, or none of the above.

electrocyclic
A)
cycloaddition
B)
sigmatropic
C)
none of the above
D)

2
Classify the reaction shown below as an electrocyclic reaction, cycloaddition, sigmatropic rearrangement, or none of the above.

electrocyclic
A)
cycloaddition
B)
sigmatropic
C)
none of the above
D)

3
Classify the reaction shown below as an electrocyclic reaction, cycloaddition, sigmatropic rearrangement, or none of the above.

electrocyclic
A)
cycloaddition
B)
sigmatropic
C)
none of the above
D)

4
Classify the reaction shown below as an electrocyclic reaction, cycloaddition, sigmatropic rearrangement, or none of the above.

electrocyclic
A)
cycloaddition
B)
sigmatropic
C)
none of the above
D)

5
Cyclopentadiene cannot be sold as a pure compound because it undergoes a cycloaddition reaction at room temperature. Which of the
following structures represents one of the two major products formed?

A)

B)

C)

D)

6
The following molecular orbital picture represents the HOMO orbital for which of the following compounds when set up for a thermal
electrocyclic reaction?

A)

B)

C)

D)

7
For the above reaction (question 7), what is the product when the starting material is heated?

A)

B)

C)

D)

8
A thermally-induced electrocyclic reaction involves which of a molecule's molecular orbitals?
HOMO-1
A)
HOMO
B)
LUMO
C)
LUMO+1
D)

9
A photochemically-induced electrocyclic reaction involves which of a molecule's molecular orbitals?
HOMO-1
A)
HOMO
B)
LUMO
C)
LUMO+1
D)

10
A molecule with an even number of pi bonds will undergo what type of electrocyclic reaction?
conrotatory, thermal
A)
conrotatory, photochemical
B)
disrotatory, thermal
C)

11
A molecule with an odd number of pi bonds will undergo what type of electrocyclic reaction?
conrotatory, thermal
A)
disrotatory, photochemical
B)
disrotatory, thermal
C)

12
Which of the following reactions converts a 1,5-diene to an isomeric 1,5-diene?
Cope rearrangement
A)
Claisen rearrangement
B)
Photochemical [2+2] reaction
C)
Diels-Alder reaction
D)

13
Which of the following reactions converts an unsaturated ether to a ,-unsaturated carbonyl compound?
Cope rearrangement
A)
Claisen rearrangement
B)
photochemical [2+2] reaction
C)
Diels-Alder reaction
D)

14
Which image correctly represents the HOMO for 1,3-butadiene?

A)

B)

C)

D)

15
Which image correctly represents the LUMO for 1,3-butadiene?

A
A)
B
B)
C
C)
D
D)

16
Which image correctly represents the lowest-energy orbital, or the one with only bonding interactions, in 1,3-butadiene?

A
A)
B
B)
C
C)
D
D)

17
Which image correctly represents the highest-energy orbital, or the one with only anti-bonding interactions, in 1,3-butadiene?

A
A)
B
B)
C
C)
D
D)

18
In the sigmatropic rearrangement shown below, which of the following choices explains the difference in products for thermal and
photochemical conditions?

(a) The photochemical product is too strained to form unless an electron in the starting material is promoted to a higher energy
orbital.
A)
(b) The photochemical product only forms when irradiated with light because the product is higher energy than the starting material.
B)
(c) The photochemical product only forms when irradiated with light because the thermal product is identical to its starting material.
C)
(d) Orbital symmetry arguments allow for the 1,3-rearrangement to occur only from the photochemical HOMO and a 1,5rearrangement to occur only from the original (thermal) HOMO.
D)

19
Which choice best describes the product distribution when A is heated in the following reaction?

The majority of the sample consists primarily of B.

A)
The majority of the sample consists primarily of C.
B)
B and C are present in approximately equal quantities.
C)
A and B are present in approximately equal quantities.
D)

20
In the reaction below, when A is irradiated with light that a diene would absorb, but is too low energy to excite an isolated alkene, which
answer best describes the product distribution?

The majority of the sample consists primarily of B.

A)
The majority of the sample consists primarily of C.
B)
B and C are present in approximately equal quantities.
C)
A and B are present in approximately equal quantities.
D)

21
Which of the following images shows the correct molecular orbitals associated with the reaction of an electron-rich diene with an electronpoor dienophile in a Diels-Alder reaction?

A
A)
B
B)
C
C)
D
D)

22
The Diels-Alder reaction is not initiated by light. Which of the following pairs of orbitals show the symmetry problem that results from
photochemical excitation of the diene in the Diels-Alder reaction, thus preventing constructive orbital overlap?

A
A)
B
B)
C
C)
D
D)

23
In the electrocyclic ring-opening reaction shown below, which answer best describes the product mixture?

The product will consist primarily of A.

A)
The product will consist primarily of B.
B)
The product will consist primarily of C.
C)
A and C are both major products.
D)

24
In the electrocyclic ring-opening reaction shown below, which answer best describes the product mixture?

The product will consist primarily of A.

A)
The product will consist primarily of B.
B)
The product will consist primarily of C.
C)
A and C are both major products.
D)

25
In the electrocyclic reaction below, which side of the reaction is favored under thermal conditions and why?

The products are favored because they are on the right side of the reaction arrow.
A)
The products are favored because ring strain is relieved.

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B)
The starting material is favored because there are more C-C single bonds.
C)
The starting material is favored due to orbital symmetry rules.
D)

26
In the electrocyclic reaction below, which side of the reaction is favored under photochemical conditions and why?

Depending on the wavelength of light used, either side of the reaction can be favored.
A)
The products are favored because ring strain is relieved.
B)
The products are favored due to orbital symmetry
C)
The starting material is favored due to orbital symmetry.
D)

27
In order for the following transformation to occur thermally, what pericyclic reactions must occur?

1. sigmatropic rearrangement, 2. electrocyclic ring-closing

A)
1. electrocyclic ring-opening, 2. Diels-Alder
B)
1. sigmatropic rearrangement, 2. Diels-Alder
C)
1. electrocyclic ring-opening, 2. electrocyclic ring-closing
D)

28
In the following two-step thermally-initiated transformation, what is the structure of the intermediate that is formed?

11

A
A)
B
B)
C
C)
D
D)

29
In the following thermal reaction, which side of the equilibrium is favored and why?

The product is favored because it is aromatic.

A)
The product is favored because there are more C-C single bonds.
B)
The starting material is favored because ring strain is relieved.
C)
The starting material is favored due to orbital symmetry rules.
D)

30
Which of the following explains why the following molecule cannot undergo an electrocyclic ring-opening reaction?

12

The double bonds needed to achieve a conjugated transition state cannot be arranged in the necessary s-cis conformation.
A)
The double bonds in this molecule are not conjugated.
B)
If this molecule underwent an electrocyclic ring-opening reaction, aromaticity would be disrupted.
C)
A 1,3-butadiene does not have the correct orbital symmetry to undergo electrocyclic reactions.
D)

31
Photochemical reaction of trans-2-butene with itself will produce which of the following products?

A and B
A)
C and D
B)
A and C
C)
B and D
D)

32
Which side of the equilibrium is favored in the Claisen rearrangement shown below and why?

The product is favored because it is aromatic.

A)
The product is facored because it has more degrees of freedom.
B)
The starting material is favored because it has lower enthalpy than the product.
C)
The starting material is favored due to orbital symmetry rules
D)

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33
If you were to perform an oxy-Cope reaction shown below, you would not isolate the product drawn on the right side of the arrow. Why not?

Equilibrium favors the starting material because it is lower in energy.

A)
The reaction cannot form the product drawn because of orbital symmetry rules.
B)
The product will undergo a tautomerization reaction to form an aldehyde.
C)
The product will aromatize to form a phenol.
D)

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