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Chapter 11: Problem 20

Would you expect cyclobutadiene to be a stable molecule? Explain.

Short Answer

Expert verified
No, cyclobutadiene is not expected to be a stable molecule. It goes against Huckel's rule and features an uneven electron distribution which both contribute to its instability.

Step by step solution

01

Analyze the Molecular Geometry

Cyclobutadiene is a four-membered ring with alternating double and single bonds. Therefore, it would be expected to have a planar structure, and each carbon atom should be sp2 hybridized, leading to 120 degree bond angles.
02

Investigate Molecular Orbital Symmetry

According to Huckel's rule, a molecule is aromatic and hence stable if it possesses a specific number of pi electrons (4n+2, where n is a non-negative integer). But cyclobutadiene has just 4 pi electrons in conjugation, going against the Huckel's rule, hence destabilizing the molecule.
03

Assess Electron Distribution

The molecule's pi electrons do not delocalize evenly due to its rectangular, not square, shape. This uneven electron distribution introduces instability.

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Most popular questions from this chapter

Draw all possible isomers for the molecule \(\mathrm{C}_{4} \mathrm{H}_{8}\).

Discuss how you can determine which of these compounds might be alkanes, cycloalkanes, alkenes, or alkynes, without drawing their formulas: (a) \(\mathrm{C}_{6} \mathrm{H}_{12}\) (b) \(\mathrm{C}_{4} \mathrm{H}_{6}\) (c) \(\mathrm{C}_{5} \mathrm{H}_{12}\) (d) \(\mathrm{C}_{7} \mathrm{H}_{14},\) (e) \(\mathrm{C}_{3} \mathrm{H}_{4}\).

How many distinct chloropentanes, \(\mathrm{C}_{5} \mathrm{H}_{11} \mathrm{Cl}\), could be produced in the direct chlorination of \(n\) -pentane, \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{3} \mathrm{CH}_{3}\) ? Draw the structure of each molecule.

Draw all the possible structural isomers for the molecule having the formula \(\mathrm{C}_{7} \mathrm{H}_{7} \mathrm{Cl}\). The molecule contains one benzene ring.

How many carbon-carbon sigma bonds are present in each of these molecules? (a) benzene, (b) cyclobutane, (c) 3-ethyl-2-methylpentane.
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