Conjugated monocyclic hydrocarbons such as benzene and cyclooctatetraene are known as annulenes. They have the general formula CnHn. The IUPAC naming conventions are that annulenes with 8 or more carbon atoms are named as [n]annulene, where n is the number of carbon atoms in the ring. Very large rings with up to 30 carbon atoms are known.Count the number of π electrons in [18]annulene, shown below, and use the rule you have deduce to predict whether the ring is aromatic. You can check your answer by examining the structure.Is [18]annulene aromatic?Open datebase entry for [18]annuleneGroup of answer choicesYes, the ring is likely to be aromaticNo, the ring is unlikely to be aromatic
Question
Conjugated monocyclic hydrocarbons such as benzene and cyclooctatetraene are known as annulenes. They have the general formula CnHn. The IUPAC naming conventions are that annulenes with 8 or more carbon atoms are named as [n]annulene, where n is the number of carbon atoms in the ring. Very large rings with up to 30 carbon atoms are known.Count the number of π electrons in [18]annulene, shown below, and use the rule you have deduce to predict whether the ring is aromatic. You can check your answer by examining the structure.Is [18]annulene aromatic?Open datebase entry for [18]annuleneGroup of answer choicesYes, the ring is likely to be aromaticNo, the ring is unlikely to be aromatic
Solution
The aromaticity of a compound can be determined using Hückel's rule, which states that a compound is aromatic if it is cyclic, planar, and has a continuous overlapping p-orbital, and the number of π electrons in the molecule is 4n+2 (where n is a whole number).
[18]annulene is a cyclic compound with 18 carbon atoms, each contributing one π electron from its double bond. Therefore, [18]annulene has 18 π electrons.
To check if this fits Hückel's rule, we need to see if 18 can be expressed in the form 4n+2.
If we solve the equation 4n+2 = 18, we get n = 4. Since 4 is a whole number, [18]annulene fits Hückel's rule and is therefore likely to be aromatic.
So, the correct answer is: Yes, the ring is likely to be aromatic.
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