Nitrogenous Compounds: Nitro Compounds and Amines
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Questions and Answers

What is the characteristic of an aromatic nitro compound?

  • The nitro group (NO2) is attached directly to an aryl group (correct)
  • The nitro group (NO2) is attached to a hydrogen atom
  • The nitro group (NO2) is attached to a halogen atom
  • The nitro group (NO2) is attached directly to an alkyl group

    • What is the hybridization of the nitrogen atom in the resonance structure of a nitroalkane?

  • sp2 (correct)
  • sp3
  • dsp2
  • sp

    • What is the product of the reaction of 1,5-dinitropentane with Zn/HCl?

  • 1,5-pentanamine
  • 1,5-diaminopentane (correct)
  • 1,5-pentanediol
  • 1,5-pentanedione

    • What is the difference between an alkyl nitrite and a nitroalkane?

    <p>They have different structural arrangements</p> Signup and view all the answers

    What is the reaction condition for the preparation of nitroalkanes from alkanes?

    <p>400°C and HNO3</p> Signup and view all the answers

    What is the product of the reaction of nitropropane with Zn/HCl?

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

    What is the characteristic of the coordinate covalent bond in the structure of nitroalkanes?

    <p>N is the donor and O is the acceptor</p> Signup and view all the answers

    What is the reagent used in the preparation of nitroalkanes from alkanes?

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

    What is the product of the reaction of alkyl halide with AgNO2?

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

    What is the type of reaction that occurs between nitroalkanes and aldehydes or ketones in the presence of a base?

    <p>Aldol type reaction</p> Signup and view all the answers

    Which of the following nitroalkanes does not react with aldehydes?

    <p>Tertiary nitroalkane</p> Signup and view all the answers

    What is the name of the compound with the structure CH3C6H3(NO2)2?

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

    What is the general mechanism for the preparation of aromatic nitro compounds?

    <p>Direct nitration</p> Signup and view all the answers

    What is the effect of a m-directing group on the nitration of substituted benzene?

    <p>It deactivates the ring towards nitration</p> Signup and view all the answers

    What is the name of the compound with the structure C6H3(NO2)3?

    <p>1,2,3-Trinitrobenzene</p> Signup and view all the answers

    What is the role of AgNO2 in the preparation of nitroalkanes from alkyl halides?

    <p>It acts as a reactant</p> Signup and view all the answers

    What is the effect of o,p-directing groups on the activity of benzene ring towards electrophiles?

    <p>They increase the activity of benzene ring towards electrophiles and require harsh conditions.</p> Signup and view all the answers

    What is the result of nitration of phenols and aniline?

    <p>A mixture of mono, di, and trinitro products is obtained along with oxidation products.</p> Signup and view all the answers

    Why is protection necessary for nitration of aromatic compounds containing OH or NH2?

    <p>To prevent oxidation of the functional group.</p> Signup and view all the answers

    What is the purpose of acylation in nitration of aromatic compounds containing OH or NH2?

    <p>To protect the functional group from oxidation.</p> Signup and view all the answers

    What is the effect of meta-directing groups on the activity of benzene ring towards electrophiles?

    <p>They decrease the activity of benzene ring towards electrophiles and require harsh conditions.</p> Signup and view all the answers

    What is the condition required for nitration of nitrobenzene?

    <p>Harsh conditions and concentrated acid.</p> Signup and view all the answers

    What is the product of nitration of toluene?

    <p>A mixture of o-nitrotoluene and p-nitrotoluene.</p> Signup and view all the answers

    Why do o,p-directing groups require mild conditions of reaction?

    <p>Because they are electron donating groups.</p> Signup and view all the answers

    What is the primary function of the acetyl group in the given reaction?

    <p>To protect the OH and NH2 groups</p> Signup and view all the answers

    What is the major product of the direct nitration of anisole using HNO3/H2SO4?

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

    What is the role of HNO3 in the mechanism of reaction B?

    <p>It provides the nitro (NO2) group which gives the p-isomer</p> Signup and view all the answers

    What is the byproduct of the reaction mechanism of reaction B?

    <p>H2O</p> Signup and view all the answers

    What is the intermediate formed in the mechanism of reaction B?

    <p>A six-centered intermediate</p> Signup and view all the answers

    What is the reagent used in the indirect method of preparing aromatic nitro compounds from amines?

    <p>Trifluoroperacetic acid</p> Signup and view all the answers

    What is the major product of the reaction of anisole with acetyl nitrate?

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

    What is the role of the acetyl group in the reaction of anisole with acetyl nitrate?

    <p>It protects the OH group and directs the nitration to give the p-isomer</p> Signup and view all the answers

    What is the purpose of using acetic anhydride in the reaction of anisole with acetyl nitrate?

    <p>To prepare the acetyl nitrate reagent</p> Signup and view all the answers

    What is the reason for the formation of the p-isomer as the major product in the reaction of anisole with acetyl nitrate?

    <p>The acetyl group directs the nitration to the p-position</p> Signup and view all the answers

    Study Notes

    Nitrogenous Compounds

    • Nitro compounds: aromatic nitro compounds and aliphatic nitro compounds
      • Aromatic nitro compounds: nitro group (NO2) attached directly to aryl group
      • Aliphatic nitro compounds: nitro group (NO2) attached directly to alkyl group

    Structure of Nitroalkanes

    • Resonance structure and resonance hybrid of nitroalkanes
    • Coordinate covalent bond between nitrogen and oxygen

    Nomenclature of Nitroalkanes

    • Nitropropane: CH3-CH2-CH2-NO2
    • 1,5-Dinitropentane: NO2-CH2-(CH2)3-CH2-NO2

    Alkyl Nitrite

    • Isomer of nitroalkanes: same number of atoms but different arrangement
    • R O N O

    Preparation of Nitroalkanes

    • From alkanes: heating with HNO3 at 400°C
    • From alkyl halides: reaction with AgNO2

    Reactions of Nitroalkanes

    • Condensation reaction with aldehydes and ketones in presence of base
    • Aldol-type reaction: active methylene group with acidic hydrogen
    • Tertiary nitroalkanes do not react with aldehydes due to absence of acidic hydrogen

    Aromatic Nitro Compounds

    • Nomenclature:
      • 1,2-Dinitrobenzene, 1,3-Dinitrobenzene, 1,2,3-Trinitrobenzene, etc.
    • Preparation:
      • Direct nitration of aromatic compounds using HNO3 and H2SO4
      • Nitration of substituted benzene: m-directing group (deactivating) and o,p-directing group (activating)
      • Protection of OH and NH2 groups using acylation

    Preparation of Aromatic Nitro Compounds (Indirect Methods)

    • From amines: oxidation using trifluoroperacetic acid or peroxytrifluoroacetic acid
    • By using o-nitrating agent (acetyl nitrate) to prepare o-nitrophenol

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    Description

    This quiz covers the basics of nitrogenous compounds, including nitro compounds, aromatic and aliphatic nitro compounds, and their structures. It also touches on amines and diazonium salts.

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