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Chapter 11: Problem 30

Benzene and cyclohexane both contain six-membered rings. Benzene is planar and cyclohexane is nonplanar. Explain.

Short Answer

Expert verified
Benzene is planar because of the delocalized 'pi bond' that forms a flat ring structure. Cyclohexane is nonplanar because its carbon atoms are linked only by single covalent bonds, which allow the molecule to adopt a 3D 'chair' conformation that minimizes repulsion between hydrogen atoms.

Step by step solution

01

Understand the structure of benzene

Benzene is a molecule formed by six carbon atoms connected in a ring, with one hydrogen atom attached to each carbon. Each carbon atom links to its two neighbors and to a hydrogen atom by single covalent bonds, and has an additional electron which forms a 'pi bond' with its neighbors above and below the plane of the ring. This 'pi bond' is delocalized, or spread out, around the entire ring, and this molecular structure gives benzene its planar shape.
02

Understand the structure of cyclohexane

Cyclohexane also forms a six-membered ring of carbon atoms each linked to two neighbors and to a hydrogen atom by single covalent bonds. However, in cyclohexane, unlike in benzene, all the bonds between carbon atoms are single bonds, which allows the molecule to adopt a variety of conformations. The conformation that minimizes repulsion between the hydrogen atoms and gives the molecule the lowest energy state is called the 'chair conformation', which is essentially a three-dimensional, nonplanar shape.
03

Compare the two structures

Benzene is planar because of its delocalized pi bond which extends above and below the plane of the carbon ring. Cyclohexane, conversely, is nonplanar because it lacks this delocalized pi bond and its shape is determined by the principle of minimum energy, which is achieved in a 3D 'chair' conformation.

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Most popular questions from this chapter

Complete this equation and identify the products: $$\mathrm{HCOOH}+\mathrm{CH}_{3} \mathrm{OH} \longrightarrow$$

Draw skeletal structures of the boat and chair forms of cyclohexane.

Name the classes to which these compounds belong: (a) \(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{OH}\) (b) \(\mathrm{CH}_{3} \mathrm{OC}_{2} \mathrm{H}_{5}\) (c) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{CHO}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COOH}\) (e) \(\mathrm{CH}_{3} \mathrm{NH}_{2}\)

A compound has the empirical formula \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\). Upon controlled oxidation, it is converted into a compound of empirical formula \(\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O},\) which behaves as a ketone. Draw possible structures for the original compound and the final compound.

Which of these amino acids are chiral: (a) \(\mathrm{CH}_{3} \mathrm{CH}\left(\mathrm{NH}_{2}\right) \mathrm{COOH}\) (b) \(\mathrm{CH}_{2}\left(\mathrm{NH}_{2}\right) \mathrm{COOH}\) (c) \(\mathrm{CH}_{2}(\mathrm{OH}) \mathrm{CH}\left(\mathrm{NH}_{2}\right) \mathrm{COOH} ?\)
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