Textbook Question
Show how the following compounds can be synthesized from benzene:
b. m-chloroethylbenzene
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19. Reactions of Aromatics: EAS and Beyond
EAS:Retrosynthesis
5:42 minutesProblem 80c
Textbook Question
How can you prepare the following compounds with benzene as one of the starting materials?
c. 
Verified step by step guidance1
Step 1: Begin with benzene as the starting material. Perform a Friedel-Crafts acylation reaction using succinic anhydride (C4H4O3) and a Lewis acid catalyst such as AlCl3. This introduces a four-carbon chain with a ketone group onto the benzene ring.
Step 2: The product from Step 1 will be benzoyl succinic acid. Cyclize this intermediate by heating it under acidic conditions to form a cyclic ketone structure. This step involves intramolecular aldol condensation.
Step 3: Perform a second Friedel-Crafts acylation reaction using another equivalent of succinic anhydride and AlCl3. This introduces another four-carbon chain with a ketone group onto the benzene ring.
Step 4: Cyclize the second intermediate under acidic conditions to form the second cyclic ketone structure. This step involves another intramolecular aldol condensation.
Step 5: The final product is the compound shown in the image, which contains two fused cyclic ketone structures attached to the benzene ring.
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5mKey Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Electrophilic Aromatic Substitution (EAS)
Electrophilic Aromatic Substitution is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring, such as benzene. This reaction is crucial for synthesizing various substituted aromatic compounds. The process typically involves the generation of a highly reactive electrophile, which then attacks the electron-rich aromatic system, leading to the formation of a sigma complex before restoring aromaticity.
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Aromaticity
Aromaticity refers to the special stability and reactivity of certain cyclic compounds that contain conjugated pi electron systems, such as benzene. For a compound to be aromatic, it must follow Hückel's rule, which states that it should have 4n + 2 pi electrons (where n is a non-negative integer). This property is essential for understanding why benzene and its derivatives undergo substitution reactions rather than addition reactions.
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Substituent Effects
Substituent effects are the influences that different groups attached to an aromatic ring have on the reactivity and orientation of electrophilic substitution reactions. Electron-donating groups (EDGs) activate the ring and direct incoming electrophiles to ortho and para positions, while electron-withdrawing groups (EWGs) deactivate the ring and direct electrophiles to the meta position. Understanding these effects is vital for predicting the outcomes of reactions involving substituted aromatic compounds.
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