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Questions and Answers
Which of the following compounds is a five membered heterocyclic compound?
Which of the following is a non-benzenoid aromatic compound?
What type of reaction is employed in the conversion of a compound using the Riemer Tiemann reaction?
How many hexagon faces are present in fullerene C60?
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What type of structures compose the network of a fullerene?
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Which of the following compounds is categorized as a six membered heterocyclic compound?
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Which of the following is correctly identified as not aromatic?
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Which reaction is utilized for Friedel Craft acylation?
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Which compound is expected to contribute the highest percentage of enol form in tautomerism?
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Which hydrogen atom plays a significant role in tautomerism between ketone and enol forms?
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What is the final product of the Darzen reaction?
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What is the final product of the Stobbe condensation reaction?
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In a reaction involving the Knoevengel reaction, what is the expected final product?
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Tautomerism involves the migration of which type of atom?
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What type of isomerism is characterized by the movement of protons?
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Which of the following statements about tautomerism is correct?
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What is the hybridization of each carbon in fullerene C60 and C70?
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Which of the following is an example of an aromatic species?
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What product is formed when naphthalene reacts with Br2?
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What is produced when naphthalene is treated with concentrated H2SO4 at 80°C?
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What compound results from the heating of thiophene with acetic anhydride in the presence of H2PO4?
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What is the result of pyrrole's reaction with benzene diazonium chloride at 5°C?
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What product is obtained from the hydrogenation of naphthalene using Ni or Pt as a catalyst?
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Which reaction converts b-naphthol to b-naphthyl amine?
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What is produced when pyridine is nitrated with KNO3/H₂SO4 at 300°C?
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What is the mechanism of the reaction where esters or β-keto esters react in the presence of a strong base?
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What is the order of kinetics for the E1 mechanism?
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How many steps are involved in the E1 mechanism?
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Which type of solvents are most effective for the E2 mechanism?
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What role does the leaving group play in the E2 mechanism?
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In the context of E2 reactions, which halide consistently provides the fastest reaction rate?
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What type of bases are favored in the E1 reaction mechanism?
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Which order of kinetics is associated with the E2 mechanism?
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What is the relationship between the substitution of the R group and the rate of an E2 reaction?
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What does the reaction of concentrated KOH followed by acidification and thermal treatment yield?
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What compound is formed when ethyl acetoacetate undergoes acid hydrolysis?
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Which reaction is specifically characterized as producing an alcohol and β-keto ester?
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When ethyl acetate is heated with sodium ethoxide, what is the resulting product?
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What product results from the reaction of acetoacetic ester with methyl bromide in the presence of sodium ethoxide?
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What is the outcome of the esterification between malonic acid and ethanol?
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Reactions of malonic ester with methyl bromide and sodium ethoxide lead to which product after hydrolysis and decarboxylation?
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What is the main product formed when diethyl malonate reacts with 1,4-dibromobutane and undergoes hydrolysis?
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Two molecules of malonic ester reacting with methylene diiodide in the presence of sodium ethoxide yields which compound after hydrolysis and decarboxylation?
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In the Beckmann Rearrangement, the migrating group is related to which position concerning the hydroxyl group?
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What product is generated when cyclohexanone oxime is treated with sulfuric acid?
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Cyclopentanone undergoing Baeyer Villiger epoxidation results in which lactone?
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The abstraction of which proton in Mc-Lafferty rearrangement leads to a six-member cyclic transition state?
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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.
