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Questions and Answers
Why do arenes predominantly undergo substitution reactions rather than addition reactions?
Why do arenes predominantly undergo substitution reactions rather than addition reactions?
- Addition reactions form more stable intermediates than substitution reactions.
- Substitution reactions are kinetically faster due to lower activation energy.
- Substitution reactions regenerate the aromatic stabilization, while addition reactions disrupt it. (correct)
- Addition reactions require higher temperatures compared to substitution reactions.
Which of the following statements accurately describes what happens to aromaticity in both substitution and addition reactions of benzene?
Which of the following statements accurately describes what happens to aromaticity in both substitution and addition reactions of benzene?
- Both substitution and addition reactions disrupt the aromaticity of the benzene ring.
- Substitution reactions preserve aromaticity, while addition reactions disrupt it. (correct)
- Both substitution and addition reactions preserve the aromaticity of the benzene ring.
- Substitution reactions disrupt aromaticity, while addition reactions preserve it.
During the hydrogenation of benzene, how does the stability of the product (cyclohexane) compare to that of the reactant (benzene)?
During the hydrogenation of benzene, how does the stability of the product (cyclohexane) compare to that of the reactant (benzene)?
- Cyclohexane is more stable due to the saturation of the ring.
- Cyclohexane is less stable due to the loss of aromatic stabilization. (correct)
- Hydrogenation has no effect on the compounds' stability.
- Cyclohexane has approximately the same stability as benzene.
What is the primary role of the delocalized electrons in arenes regarding their reactivity?
What is the primary role of the delocalized electrons in arenes regarding their reactivity?
Which statement reflects the energy changes associated with benzene undergoing an addition reaction that disrupts its aromatic system?
Which statement reflects the energy changes associated with benzene undergoing an addition reaction that disrupts its aromatic system?
Flashcards
Electrophilic Aromatic Substitution
Electrophilic Aromatic Substitution
A reaction where an electrophile (electron-seeking species) attacks the benzene ring.
Aromatic Stabilization
Aromatic Stabilization
The delocalization of electrons within the benzene ring, providing stability.
Substitution Reactions (Arenes)
Substitution Reactions (Arenes)
Reactions that replace one group on the benzene ring with another, preserving aromaticity..
Addition Reactions (Arenes)
Addition Reactions (Arenes)
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Hydrogenation of Arenes
Hydrogenation of Arenes
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Study Notes
- Electrophiles attack the benzene ring after being generated.
- Arenes mainly undergo substitution reactions because of electron delocalization, also called aromatic stabilization.
- Aromaticity is restored in substitution reactions.
- Aromaticity is not restored and is sometimes completely lost in addition reactions.
- The hydrogenation of arenes is an addition reaction where aromatic stabilization is completely lost.
- The cyclohexane formed through hydrogenation is less stable than benzene.
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Description
Electrophiles generated then attack the benzene ring. Arenes undergo substitution to maintain electron delocalization and aromatic stability. Unlike substitution, addition reactions don't restore aromaticity, for example, hydrogenation of arenes results in the loss of aromatic stabilization.