Polynuclear and Heteronuclear Aromatic Compounds
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Questions and Answers

Which of the following compounds is a five membered heterocyclic compound?

  • Pyrrole (correct)
  • Pyridine
  • Tropone
  • Annulene
  • Which of the following is a non-benzenoid aromatic compound?

  • Benzene
  • Anthracene
  • Naphthalene
  • Azulene (correct)
  • What type of reaction is employed in the conversion of a compound using the Riemer Tiemann reaction?

  • Elimination reaction
  • Addition reaction
  • Substitution reaction (correct)
  • Rearrangement reaction
  • How many hexagon faces are present in fullerene C60?

    <p>20</p> Signup and view all the answers

    What type of structures compose the network of a fullerene?

    <p>Pentagons and hexagons</p> Signup and view all the answers

    Which of the following compounds is categorized as a six membered heterocyclic compound?

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

    Which of the following is correctly identified as not aromatic?

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

    Which reaction is utilized for Friedel Craft acylation?

    <p>Friedel Craft Reaction</p> Signup and view all the answers

    Which compound is expected to contribute the highest percentage of enol form in tautomerism?

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

    Which hydrogen atom plays a significant role in tautomerism between ketone and enol forms?

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

    What is the final product of the Darzen reaction?

    <p>α, β-epoxy ester</p> Signup and view all the answers

    What is the final product of the Stobbe condensation reaction?

    <p>α, β-unsaturated acid</p> Signup and view all the answers

    In a reaction involving the Knoevengel reaction, what is the expected final product?

    <p>α, β-unsaturated acid</p> Signup and view all the answers

    Tautomerism involves the migration of which type of atom?

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

    What type of isomerism is characterized by the movement of protons?

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

    Which of the following statements about tautomerism is correct?

    <p>It can involve keto-enol interconversion.</p> Signup and view all the answers

    What is the hybridization of each carbon in fullerene C60 and C70?

    <p>sp2</p> Signup and view all the answers

    Which of the following is an example of an aromatic species?

    <p>Cyclopentadienyl cation</p> Signup and view all the answers

    What product is formed when naphthalene reacts with Br2?

    <p>1-bromo naphthalene</p> Signup and view all the answers

    What is produced when naphthalene is treated with concentrated H2SO4 at 80°C?

    <p>Naphthalene 1-sulphonic acid</p> Signup and view all the answers

    What compound results from the heating of thiophene with acetic anhydride in the presence of H2PO4?

    <p>2-acetyl thiophene</p> Signup and view all the answers

    What is the result of pyrrole's reaction with benzene diazonium chloride at 5°C?

    <p>2-phenyl azo-pyrrole</p> Signup and view all the answers

    What product is obtained from the hydrogenation of naphthalene using Ni or Pt as a catalyst?

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

    Which reaction converts b-naphthol to b-naphthyl amine?

    <p>Bucherer reaction</p> Signup and view all the answers

    What is produced when pyridine is nitrated with KNO3/H₂SO4 at 300°C?

    <p>3-nitro pyridine</p> Signup and view all the answers

    What is the mechanism of the reaction where esters or β-keto esters react in the presence of a strong base?

    <p>Claisen Condensation</p> Signup and view all the answers

    What is the order of kinetics for the E1 mechanism?

    <p>First order</p> Signup and view all the answers

    How many steps are involved in the E1 mechanism?

    <p>Two steps</p> Signup and view all the answers

    Which type of solvents are most effective for the E2 mechanism?

    <p>Polar aprotic solvents</p> Signup and view all the answers

    What role does the leaving group play in the E2 mechanism?

    <p>A better leaving group increases the reaction speed</p> Signup and view all the answers

    In the context of E2 reactions, which halide consistently provides the fastest reaction rate?

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

    What type of bases are favored in the E1 reaction mechanism?

    <p>Weak bases</p> Signup and view all the answers

    Which order of kinetics is associated with the E2 mechanism?

    <p>Second order</p> Signup and view all the answers

    What is the relationship between the substitution of the R group and the rate of an E2 reaction?

    <p>More substituted halides react faster</p> Signup and view all the answers

    What does the reaction of concentrated KOH followed by acidification and thermal treatment yield?

    <p>Propionic acid and ethanol</p> Signup and view all the answers

    What compound is formed when ethyl acetoacetate undergoes acid hydrolysis?

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

    Which reaction is specifically characterized as producing an alcohol and β-keto ester?

    <p>Claisen condensation</p> Signup and view all the answers

    When ethyl acetate is heated with sodium ethoxide, what is the resulting product?

    <p>Ethyl alcohol</p> Signup and view all the answers

    What product results from the reaction of acetoacetic ester with methyl bromide in the presence of sodium ethoxide?

    <p>Ethyl methyl ketone</p> Signup and view all the answers

    What is the outcome of the esterification between malonic acid and ethanol?

    <p>Malonic ester</p> Signup and view all the answers

    Reactions of malonic ester with methyl bromide and sodium ethoxide lead to which product after hydrolysis and decarboxylation?

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

    What is the main product formed when diethyl malonate reacts with 1,4-dibromobutane and undergoes hydrolysis?

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

    Two molecules of malonic ester reacting with methylene diiodide in the presence of sodium ethoxide yields which compound after hydrolysis and decarboxylation?

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

    In the Beckmann Rearrangement, the migrating group is related to which position concerning the hydroxyl group?

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

    What product is generated when cyclohexanone oxime is treated with sulfuric acid?

    <p>𝜀-Caprolactam</p> Signup and view all the answers

    Cyclopentanone undergoing Baeyer Villiger epoxidation results in which lactone?

    <p>𝛿-Valerolactone</p> Signup and view all the answers

    The abstraction of which proton in Mc-Lafferty rearrangement leads to a six-member cyclic transition state?

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

    Study Notes

    Polynuclear and Heteronuclear Aromatic Compounds

    • Pyrrole is a five-membered heterocyclic compound.
    • Pyridine is a six-membered heterocyclic compound.
    • Azulene is a non-benzenoid aromatic compound.
    • Fullerene is composed of a network of pentagons and hexagons.
    • C60 fullerene has 20 hexagon faces.
    • C70 fullerene has 25 hexagon faces.
    • Each carbon in fullerene C60 and C70 is sp2 hybridized.
    • Cyclopentadienyl cation and cyclopentadienyl anion are aromatic species.
    • Naphthalene on treatment with Br2 forms 1-bromo naphthalene.
    • Naphthalene on treatment with conc. H2SO4 at 80C gives naphthalene 1- sulphonic acid.
    • Thiophene on heating with acetic anhydride in the presence of H2PO4 gives 2-acetylthiophene.
    • Naphthalene on treatment with conc. H2SO4 at 160C gives naphthalene 2- sulphonic acid.
    • Pyrrole reacts with benzene diazonium chloride at 5C to form 2-phenylazo-pyrrole.
    • Naphthalene upon Ni or Pt catalysed hydrogenation gives decalin.
    • Pyrrole on treatment with acetyl chloride in the presence of AlCl3 gives 2-acetylpyrrole.
    • Pyridine on heating with Br2 at 300C gives 2-bromopyridine and 3,5-dibromopyridine.
    • Pyridine on nitration with KNO3/H2SO4 at 300C gives 3-nitropyridine.
    • Bucherer reaction is used to convert β-naphthol to β-naphthylamine.
    • Friedel Crafts reaction is a key reaction for adding alkyl or acyl substituents to aromatic rings.

    Active Methylene Compounds

    • Claisen condensation is a carbon-carbon bond forming reaction that occurs between two esters or a β-keto ester or a β-diketone in the presence of a strong base.
    • Diethyl malonate is an example of an active methylene compound.
    • Tautomerism refers to the interconversion of two isomers, or tautomers, that differ in the position of a proton and a double bond.
    • In tautomerism, the alpha hydrogen plays an important role.
    • Acetone has the highest percentage of enol form among the given compounds.
    • The final product of the Darzen reaction is an α, β-epoxy ester.
    • The final product of the Stobbe condensation is an α, β-unsaturated acid.
    • The final product of the Knoevenagel reaction is an α, β-unsaturated acid.
    • Ethyl acetoacetate on acid hydrolysis with dilute HCl forms acetoacetic acid.
    • Claisen condensation is a base-catalyzed condensation of two esters to form an alcohol and β-keto ester.
    • Ethyl acetate on heating with sodium ethoxide gives ethyl alcohol.
    • Acetoacetic ester on reaction with methyl bromide in the presence of sodium ethoxide followed by hydrolysis and decarboxylation gives Methyl n-propyl ketone.

    Rearrangement Reactions

    • Beckmann rearrangement is the acid-catalyzed rearrangement of an oxime to an amide.
    • In the Beckmann rearrangement, the group trans with respect to the oxygen hydroxyl group migrates.
    • The group with respect to the oxygen hydroxyl group migrates in a trans fashion.
    • Cyclohexanone oxime on treatment with sulphuric acid gives 𝜺-caprolactam.
    • Cyclohexanone on treatment with trifluoroacetic acid gives 𝜺-caprolactam.
    • Cyclopentanone, upon Baeyer Villiger epoxidation, gives 𝜹-valerolactone.
    • Favorskii rearrangement produces a cyclopropanone intermediate.
    • Curtius rearrangement is the thermal rearrangement of an acid azide in a nonpolar solvent.
    • The reagent used in the Schmidt reaction is hydrazoic acid.
    • Claisen rearrangement is a type of sigmatropic rearrangement.
    • McLafferty rearrangement proceeds through the formation of a radical cation.
    • In McLafferty rearrangement, the abstraction of a proton in a six-membered cyclic transition state occurs.

    Elimination Reactions

    • When two atoms or groups are removed from the same atom, the reaction is known as a 1,1-elimination.
    • 𝜶-elimination reactions, 𝜷-elimination reactions, and 𝜸-elimination reactions are classified based on the relative position of the elimination groups.
    • The E1 mechanism is a two-step reaction proceeding through a carbocation intermediate.
    • The E1 mechanism is first order, meaning its rate depends on the concentration of the substrate only.
    • More substituted halides react faster in the E1 mechanism: R3CX > R2CHX > RCH2X.
    • E1 is favored by weaker bases such as H2O and ROH.
    • A better leaving group makes the E1 reaction faster because the bond to the leaving group is partially broken in the rate-determining step.
    • Polar protic solvents that solvate the ionic intermediates are needed for the E1 reaction.
    • The E2 mechanism is a one-step reaction involving a concerted elimination of the leaving group and hydrogen.
    • The E2 mechanism is second order, meaning its rate depends on the concentration of both the substrate and the base.
    • More substituted halides react faster in the E2 mechanism: R3CX > R2CHX > RCH2X.
    • E2 is favored by strong bases.
    • A better leaving group makes the E2 reaction faster.
    • E2 is favored by polar aprotic solvents.
    • The rate of the E2 mechanism is expressed as Rate = [Substrate] [Base]
    • The relative rates of the E2 mechanism for different leaving groups support the mechanism.
    • As the strength of the leaving group increases, the rate of the E2 reaction gets higher.
    • In the E2 mechanism, the C-X Bond breaks slowly in the rate-determining step.

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    Description

    This quiz explores the fascinating world of polynuclear and heteronuclear aromatic compounds. Key topics include the properties and reactions of pyrrole, pyridine, azulene, and fullerenes, along with various derivatives of naphthalene. Test your knowledge on the essential reactions and structural characteristics of these compounds.

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