The following involves two pericyclic reactions. Which combination indicates correctly the types of reaction involved?

[4+2] cycloaddition + cheletropic reaction

[4+2] cycloaddition + [2+2] cycloreversion

cheletropic reaction + [4+2] cycloaddition

[4+2] cycloaddition + [4+1] cycloreversion

Quiz Competition On Pericyclic Reactions

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| By Ashok Pise

Ashok Pise

Community Contributor

Quizzes Created: 1 | Total Attempts: 1,483

Questions: 10 | Attempts: 1,483 | Updated: Feb 19, 2024

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Questions and Answers

1.

Which of the following dienophiles is the most reactive with buta-1,3-diene?
- A.
  
  Option 1
- B.
  
  Option 2
- C.
  
  Option 3
- D.
  
  Option 4
Correct Answer
C. Option 3

Explanation
Compound (c) is the dienophile with the best combination of low steric hindrance and a low-energy LUMO (which is caused by the electron-withdrawing anhydride residue)

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2.

Which of the following dienes cannot undergo Diels-Alder reactions?
- A.
  
  Option 1
- B.
  
  Option 2
- C.
  
  Option 3
- D.
  
  Option 4
Correct Answer
D. Option 4

Explanation
A diene has to be able to assume an s-cis conformation in order to undergo Diels-Alder reactions, and (d) has a constrained s-trans structure

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3.

Which of adducts (a)-(d) is the main product of the following Diels-Alder reaction?
- A.
  
  Option 1
- B.
  
  Option 2
- C.
  
  Option 3
- D.
  
  Option 4
Correct Answer
B. Option 2

Explanation
The relative configurations of the diene and dienophile are preserved in the concerted syn addition of a Diels-Alder reaction. For the stereochemistry of Diels-Alder reactions

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4.

Which of the following is the main product in the ozonolysis of 1,4-dimethylcyclohexene followed by a reductive workup with Zn and ethanoic acid?
- A.
  
  Option 1
- B.
  
  Option 2
- C.
  
  Option 3
- D.
  
  Option 4
Correct Answer
C. Option 3

Explanation
The products of ozonolysis followed by a reductive workup are aldehyde(s) and/or ketone(s). Note the position of the methyl substituent in the ring-opened product. For ozonolysis of alkenes

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5.

Which of the following is the main product in the ozonolysis of 1,5-dimethylcyclohexene followed by a workup with aqueous H₂O₂?
- A.
  
  Option 1
- B.
  
  Option 2
- C.
  
  Option 3
- D.
  
  Option 4
Correct Answer
C. Option 3

Explanation
The products of ozonolysis followed by an oxidative workup are carboxylic acid(s) and/or ketone(s). Note that the position of the methyl substituent in the ring-opened product. For ozonolysis of alkenes

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6.

Which of phenols (a)-(d) is the main product of the following thermal rearrangement?
- A.
  
  Option 1
- B.
  
  Option 2
- C.
  
  Option 3
- D.
  
  Option 4
Correct Answer
D. Option 4

Explanation
The reaction is a Claisen rearrangement which is a type of [3,3] sigmatropic rearrangement

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7.

Which of the following reactions is not thermally allowed?
- A.
  
  Option 1
- B.
  
  Option 2
- C.
  
  Option 3
- D.
  
  Option 4
Correct Answer
A. Option 1

Explanation
For some orbital symmetry controlled reactions, see pp. 478-5. Reaction (a) is a [2+2] cycloaddition, (b) a [3,3] sigmatropic rearrangement, (c) an electrocyclic reaction, and (d) an ene reaction.

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8.

Which of the following reactions is classified as an ene reaction?
- A.
  
  Option 1
- B.
  
  Option 2
- C.
  
  Option 3
- D.
  
  Option 4
Correct Answer
D. Option 4

Explanation
Reactions (a) and (b) are both [3,3] sigmatropic rearrangements, (c) an electrocyclic reaction, and (d) an ene reaction.

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9.

The following involves two pericyclic reactions. Which combination indicates correctly the types of reaction involved?
- A.
  
  [4+2] cycloaddition + [2+2] cycloreversion
- B.
  
  Cheletropic reaction + [4+2] cycloaddition
- C.
  
  [4+2] cycloaddition + [4+1] cycloreversion
- D.
  
  [4+2] cycloaddition + cheletropic reaction
Correct Answer
D. [4+2] cycloaddition + cheletropic reaction

Explanation
Carbon monoxide is lost from the intermediate adduct

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10.

Which of the following is classified as an electrocyclic reaction?
- A.
  
  Option 1
- B.
  
  Option 2
- C.
  
  Option 3
- D.
  
  Option 4
Correct Answer
A. Option 1

Explanation
Electrocyclic reactions involve the cyclization of a conjugated polyene, where a pi bond is formed by the overlap of two p orbitals from adjacent atoms. This is exactly what happens in Option 1. The conjugated diene rearranges to form a cyclobutene ring with a new sigma bond between the two carbons that were originally part of the double bonds.

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Current Version
Feb 19, 2024

Quiz Edited by
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Apr 21, 2020

Quiz Created by
Ashok Pise

Quiz Competition On Pericyclic Reactions

Which of the following dienophiles is the most reactive with buta-1,3-diene?

Which of the following dienes cannot undergo Diels-Alder reactions?

Which of adducts (a)-(d) is the main product of the following Diels-Alder reaction?

Which of the following is the main product in the ozonolysis of 1,4-dimethylcyclohexene followed by a reductive workup with Zn and ethanoic acid?

Which of the following is the main product in the ozonolysis of 1,5-dimethylcyclohexene followed by a workup with aqueous H2O2?

Which of phenols (a)-(d) is the main product of the following thermal rearrangement?

Which of the following reactions is not thermally allowed?

Which of the following reactions is classified as an ene reaction?

The following involves two pericyclic reactions. Which combination indicates correctly the types of reaction involved?

Which of the following is classified as an electrocyclic reaction?

Which of the following is the main product in the ozonolysis of 1,5-dimethylcyclohexene followed by a workup with aqueous H₂O₂?