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Which of the following compounds is not aromatic?

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Question: Which of the following compounds is not aromatic?

Options:

  1. Naphthalene
  2. Benzene
  3. Cyclooctatetraene
  4. Anthracene

Correct Answer: Cyclooctatetraene

Solution: 

Cyclooctatetraene is not aromatic because it does not satisfy Huckel\'s rule; it is non-planar and does not have a continuous ring of p orbitals.

Which of the following compounds is not aromatic?

Practice Questions

Q1
Which of the following compounds is not aromatic?
  1. Naphthalene
  2. Benzene
  3. Cyclooctatetraene
  4. Anthracene

Questions & Step-by-Step Solutions

Which of the following compounds is not aromatic?
Correct Answer: Cyclooctatetraene
  • Step 1: Understand what aromatic compounds are. Aromatic compounds are special types of cyclic (ring-shaped) molecules that have a specific stability due to their electron structure.
  • Step 2: Learn about Huckel's rule. This rule states that for a compound to be aromatic, it must have (4n + 2) π (pi) electrons, where n is a whole number (0, 1, 2, ...).
  • Step 3: Identify the structure of cyclooctatetraene. Cyclooctatetraene is a ring made up of 8 carbon atoms with alternating double bonds.
  • Step 4: Check the number of π electrons in cyclooctatetraene. It has 8 π electrons, which does not fit Huckel's rule (4n + 2).
  • Step 5: Determine if cyclooctatetraene is planar. Aromatic compounds must be planar (flat) to allow for overlapping p orbitals. Cyclooctatetraene is not planar; it adopts a non-planar 'tub' shape.
  • Step 6: Conclude that cyclooctatetraene is not aromatic because it does not meet Huckel's rule and is not planar.
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