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Chapter 11: Problem 29

Comment on the extra stability of benzene compared to ethylene. Why does ethylene undergo addition reactions while benzene usually undergoes substitution reactions?

Short Answer

Expert verified
Benzene has extra stability compared to ethylene owing to the resonance-stabilized aromatic ring structure, enabling delocalization of pi electrons. While ethylene readily undergoes addition reactions due to its double bond, benzene prefers substitution reactions to maintain its aromaticity and stability.

Step by step solution

01

Structure and Stability

Ethylene is composed of two carbon atoms which are double-bonded. On the other hand, benzene is an aromatic compound with alternating double and single bonds, forming a resonance-stabilized ring structure. The delocalized pi electron system provides an increased stability to benzene as compared to ethylene.
02

Reactivity and Type of Reactions

Ethylene, with its double bond, can undergo addition reactions. It's because the pi electrons in the double bond can easily break and new atoms or groups can add across the double bond. On the contrary, benzene, due to its extra stability and fully delocalized electron cloud, typically resists addition reactions because an addition would disrupt its aromatic system. So, benzene prefers to undergo substitution reactions where one hydrogen atom gets replaced by another atom or group of atoms, thereby maintaining its stability.
03

Summary

Therefore, the extra stability of benzene as compared to ethylene is due to the aromaticity and a fully delocalized electron system in its ring structure. Also, while ethylene readily undergoes addition reactions, benzene more commonly takes part in substitution reactions to conserve its stability.

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Most popular questions from this chapter

Write structures for the compounds shown below: (a) 1-bromo-3-methylbenzene, (b) 1-chloro-2-propylbenzene, (c) 1,2,4,5 -tetramethylbenzene.

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Identify the functional groups in each of these molecules: (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{COOC}_{2} \mathrm{H}_{5}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\)

Generally aldehydes are more susceptible to oxidation in air than are ketones. Use acetaldehyde and acetone as examples and show why ketones such as acetone are more stable than aldehydes in this respect.

Why is it that alkanes and alkynes, unlike alkenes, have no geometric isomers?
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