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

  1. Jan 27, 2016 #1
    1. The problem statement, all variables and given/known data
    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.

    2. Relevant equations

    none.

    3. 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?
     
  2. jcsd
  3. Jan 28, 2016 #2

    DrDu

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    Science Advisor

    If you would do the clemenson reduction before nitration?
     
  4. Feb 1, 2016 #3
    It sounds right as in you didnt do anything that you would blow you up. But no, this wont 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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