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Exam 16: Aromatic Compounds

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Question 1

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Is cyclooctatetraene a planar molecule? Explain.

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No. In addition to increasing other forms of strain, a planar conformation would make this molecule antiaromatic.

Question 2

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When cyclohexene is treated with KMnO₄, H₂O, the syn-1,2-diol is produced. What reaction occurs when benzene is similarly treated?

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No reactio...

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Question 3

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Which of the following compounds may correctly be classified as being aromatic? (More than one answer is possible.)

Provide an acceptable name for the compound below.

Is the molecule below aromatic, antiaromatic, or nonaromatic?

Which of the following structures, if flat, would be classified as antiaromatic?

An unknown compound gives the following spectral data. Propose a structure that is consistent with this information. In addition, show the fragmentations that give the 91 and 122 peaks in the MS. MS (m/z): 91, 108 and 122 (M⁺) ¹H NMR (δ): 7.05(2H, d), 6.78 (2H, d), 3.7 (3H, s), 2.26 (3H, s)

Provide the structure of 4-isopropylbenzaldehyde.

Classify cyclopropenyl cation as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network

Provide an acceptable name for the compound below.

Describe the occupied π molecular orbitals in the ground state of cyclobutadiene.

Provide the name of the compound shown below.

Provide the structure of o-bromostyrene.

Provide the structure of sodium cyclopentadienide.

When toluene is treated with bromine (shown below), the bromine doesn't react with the double bond to form a viscinal dihalide, but instead a substitution of one of the benzylic hydrogens takes place. Why?

Show how the participating p orbitals interact to form the highest energy π molecular orbital of benzene.

Classify the compound below as aromatic antiaromatic, or nonaromatic. Assume planarity of the π network.

Circle and name the aromatic heterocycles in the following structure, which has been found to be effective against inflammatory diseases including Alzheimer's disease and rheumatoid arthritis (J. Med. Chem. 2007, 4728).

Is the molecule below aromatic, antiaromatic, or nonaromatic?

Is the all-cis form of [10]annulene aromatic? Explain.