Organic chem2 - Synthesis of 1-chloro-3-ethyl-5-nitrobenzene

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The synthesis of 1-chloro-3-ethyl-5-nitrobenzene involves starting with benzene and performing a Friedel-Crafts alkylation followed by chlorination using Cl2 and FeCl3. The nitro group is introduced through nitration with HNO3 and H2SO4. Concerns were raised regarding the order of reactions, particularly whether a Clemmensen reduction would affect the nitro group if performed after nitration. It was clarified that this approach would yield a structural isomer rather than the desired product due to the directing effects of the substituents. The discussion emphasizes the importance of considering the directing abilities of groups in aromatic substitution reactions.
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Homework Statement


Synthesize 1-chloro-3-ethyl-5-nitrobenzene. Assume you have benzene, chloroethane, acetyl chloride, NaCl, Cl2, AlCl3, FeCl3, NH2NH2, Zn, KOH, HNO3, H2SO4, and HCl.

Homework Equations



none.

The Attempt at a Solution


I started with benzene. I did a Friedel-crafts on benzene. Then, I reacted with Cl2 and FeCl3. Then I reacted with HNO3/H2SO4 to give the nitro group. Finally, I did a clemmenson reduction to get rid of the carbonyl. Does this sound right? My concern is, will the nitro group be affected by the reduction at the end?
 
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If you would do the clemenson reduction before nitration?
 
It sounds right as in you didnt do anything that you would blow you up. But no, this won't give you the product you want. it will give you a structural isomer of it. While adding the reagents, you forgot about their directing ability. Try again.
 
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