Organic Chemistry Nitro Group Reduction
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Questions and Answers

What is the result of the reaction between NH3 and HNO2 at 100°C?

  • Formation of NO2 (correct)
  • Formation of NaNO2
  • Formation of NaHS
  • Formation of OCH3
  • Which of the following is a method used for the reduction of nitro groups?

  • Thermal reduction
  • Electrochemical reduction
  • Catalytic reduction (correct)
  • Photochemical reduction
  • In the mechanism of the nitro group reaction, which species acts slowly in the process?

  • N2
  • N (correct)
  • NaNO2
  • O2
  • What compound is formed when NaHS reacts with NaNO2?

    <p>NO2</p> Signup and view all the answers

    Which of the following best describes the byproducts of the reaction involving CH3ONa?

    <p>Formation of HO and NaNO2</p> Signup and view all the answers

    What is the major product of the nitration of anisole?

    <p>o-nitroanisole</p> Signup and view all the answers

    Which reagent is used alongside concentrated sulfuric acid in the nitration of benzene derivatives?

    <p>HNO3</p> Signup and view all the answers

    Which mechanism facilitates the nitration in the case of anisole?

    <p>Electrophilic aromatic substitution</p> Signup and view all the answers

    What product results from the nitration of phenol?

    <p>A mixture of mono-, di-, and trinitro products</p> Signup and view all the answers

    What type of substituted benzene is likely to produce a pure o-isomer upon nitration?

    <p>Acetylated anisole</p> Signup and view all the answers

    Study Notes

    Reaction of Nitro Group

    • Nitro group can be reduced by catalytic or chemical reduction methods.

    Catalytic Reduction

    • Nitro group can be reduced to an amino group by using hydrogen gas and a catalyst like nickel, platinum, or palladium.

    Chemical Reduction

    • The reduction product of a nitro group depends on the strength of the reducing agent and the pH of the medium.

    Reduction in Acidic Medium

    • In acidic medium, nitro group is reduced to an amino group using a strong reducing agent like iron, tin, or zinc with hydrochloric acid or SnCl2.

    Reduction in Neutral Medium

    • In neutral medium, nitro group is reduced to N-phenyl hydroxylamine using zinc with ammonium chloride.

    Reduction in Alkaline Medium

    • In alkaline medium, nitro group can be reduced to different products depending on the reducing agent and the reaction conditions.
    • Using NaOH/CH3OH, a nitro group can be reduced to an azoxybenzene.
    • Using SnCl2/NaOH, it can be further reduced to an azobenzene.
    • Using Zn/HCl, it forms an azobenzene.
    • Using Zn/NaOH, a hydrazobenzene can be formed.
    • Using SnCl2/HCl, it is reduced to corresponding amine.

    Reactions of Aromatic Nitro Compounds

    • Aromatic nitro compounds undergo reactions involving the benzene ring or the nitro group.

    Reactions of Benzene Ring

    • Aromatic nitro compounds undergo electrophilic aromatic substitution (EAS) reactions, but the nitro group deactivates the ring and directs the incoming electrophile to the meta position.

    • The nitro group is electron-withdrawing and meta-directing, restricting the ring's reactivity towards electrophilic aromatic substitution such as Friedel-Crafts alkylation or acylation.

    • Nitro groups activate the ring toward nucleophilic aromatic substitution reactions. This activation occurs due to the electron-withdrawing and resonance effects of the nitro group, making it an excellent leaving group.

    • The nitro group directs incoming nucleophiles to the ortho and para positions.

    • Nucleophilic aromatic substitution reactions typically involve a "Meisenheimer intermediate" which is stabilized by the nitro group.

    • There are three main categories of nucleophilic aromatic substitution reactions:

      • Substitution of hydride at the ortho and para positions to nitro group.
      • Substitution of halide at the ortho or para position to nitro group.
      • Substitution of nitro group if multiple nitro groups are at ortho or para positions to each other.

    Reactions of Nitro Group

    • The nitro group can undergo reactions like reduction or participate in the reactions of the benzene ring, such as EAS or SNAr.

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    Description

    This quiz covers the various methods of reducing a nitro group into different functional groups in organic chemistry. It includes catalytic and chemical reduction techniques as well as the effects of different pH levels on the reduction process. Test your understanding of these important reduction reactions and their conditions.

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