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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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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Benzene
Benzene is a fascinating molecule in the world of organic chemistry. It is composed of six carbon atoms that form a hexagonal ring. Each carbon atom in benzene is bonded to a single hydrogen atom, making the molecular formula for benzene C 6H 6. What makes benzene truly unique is the nature of its chemical bonds. The carbon atoms in benzene are connected to each other by single bonds and an additional type of bond known as a pi bond.

The pi bonds are formed from the delocalization of electrons across the carbon atoms. This means that instead of being concentrated between two atoms, the pi electrons are spread over the entire ring structure. This delocalization gives benzene its characteristic stability and planarity. The electrons above and below the plane of the ring cause benzene to have a flat, or planar, shape. This structural feature is crucial for various chemical reactions, making benzene an essential component in organic chemistry.
Cyclohexane
Cyclohexane also contains a six-membered ring, but its structure is quite different from that of benzene. Cyclohexane's carbon atoms are each bonded to two other carbon atoms and two hydrogen atoms, but it differs in having only single covalent bonds throughout. This lack of additional pi bonding means that cyclohexane can adopt multiple shapes, or conformations.

The most stable conformation of cyclohexane is known as the "chair conformation." This form minimizes the repulsion between electron clouds of the hydrogen atoms attached to the ring. Therefore, unlike benzene, cyclohexane does not span a flat, planar shape; it is nonplanar. These differences in structure and conformation result in cyclohexane behaving differently than benzene in terms of reactivity and physical properties.
Molecular Structure
The concept of molecular structure involves understanding how the arrangement of atoms and bonds in a molecule determines its properties and behavior. Both benzene and cyclohexane emphasize how molecular structure affects the physical characteristics of a compound.

In benzene, the delocalized pi bonds create a stable planar shape, which contributes to its unique chemical properties. This planarity is a result of resonance, where the electrons can be imagined to hop or resonate between different carbons continuously.
  • Benzene's structure leads to chemical stability and influences its reactivity.
  • The molecule's flat nature is critical to its role in forming compounds like aromatic hydrocarbons.
Cyclohexane, with its chair conformation, highlights the significance of 3D molecular structures.
  • The nonplanar shape influences how cyclohexane molecules interact with each other and other substances.
  • This contributes to cyclohexane being less reactive but useful as a non-polar solvent in organic reactions.
Understanding these structures and their resultant intermolecular interactions allows chemists to predict and manipulate chemical behavior effectively.

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Most popular questions from this chapter

Fats and oils are names for the same class of compounds, called triglycerides, which contain three ester groups in which \(\mathrm{R}, \mathrm{R}^{\prime},\) and \(\mathrm{R}^{\prime \prime}\) represent long hydrocarbon chains. (a) Suggest a reaction that leads to the formation of a triglyceride molecule, starting with glycerol and carboxylic acids (see p. 398 for structure of glycerol). (b) In the old days, soaps were made by hydrolyzing animal fat with lye (a sodium hydroxide solution). Write an equation for this reaction. (c) The difference between fats and oils is that at room temperature, the former are solid and the latter are liquids. Fats are usually produced by animals, whereas oils are commonly found in plants. The melting points of these substances are determined by the number of \(\mathrm{C}=\mathrm{C}\) bonds (or the extent of unsaturation) present- -the larger the number of \(\mathrm{C}=\mathrm{C}\) bonds, the lower the melting point and the more likely the substance is a liquid. Explain. (d) One way to convert liquid oil to solid fat is to hydrogenate the oil, a process by which some or all of the \(\mathrm{C}=\mathrm{C}\) bonds are converted to \(\mathrm{C}-\mathrm{C}\) bonds. This procedure prolongs shelf life of the oil by removing the more reactive \(\mathrm{C}=\mathrm{C}\) group and facilitates packaging. How would you carry out such a process (that is, what reagents and catalyst would you employ)? (e) The degree of unsaturation of oil can be determined by reacting the oil with iodine, which reacts with the \(\mathrm{C}=\mathrm{C}\) as follows: The procedure is to add a known amount of iodine to the oil and allow the reaction to go to completion. The amount of excess (unreacted) iodine is determined by titrating the remaining iodine with a standard sodium thiosulfate \(\left(\mathrm{Na}_{2} \mathrm{~S}_{2} \mathrm{O}_{3}\right)\) solution: $$\mathrm{I}_{2}+2 \mathrm{Na}_{2} \mathrm{~S}_{2} \mathrm{O}_{3} \longrightarrow \mathrm{Na}_{2} \mathrm{~S}_{4} \mathrm{O}_{6}+2 \mathrm{NaI}$$ The number of grams of iodine that reacts with \(100 \mathrm{~g}\) of oil is called the iodine number. In one case, \(43.8 \mathrm{~g}\) of \(\mathrm{I}_{2}\) were treated with \(35.3 \mathrm{~g}\) of corn oil. The excess iodine required \(20.6 \mathrm{~mL}\) of \(0.142 \mathrm{M} \mathrm{Na}_{2} \mathrm{~S}_{2} \mathrm{O}_{3}\) for neutralization. Calculate the iodine number of the corn oil.

The compound \(\mathrm{CH}_{3}-\mathrm{C} \equiv \mathrm{C}-\mathrm{CH}_{3}\) is hydrogenated to an alkene using platinum as the catalyst. If the product is the pure cis isomer, what can you deduce about the mechanism?

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.

Write the structures of three alkenes that yield 2-methylbutane on hydrogenation.

What do "saturated" and "unsaturated" mean when applied to hydrocarbons? Give examples of a saturated hydrocarbon and an unsaturated hydrocarbon.

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