Furan | Lec.7
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Questions and Answers

What is the product formed from the bromination of furan in the presence of alcohol?

  • Mercuration product
  • Oxidation product
  • Pyrrole
  • 2,5-dialkoxy-2, 5-dihydrofurans (correct)

Why can furan behave as a diene in Diels-Alder reactions?

  • Due to the addition of sulfur compounds
  • Due to the high electronegativity of the oxygen atom (correct)
  • Due to the presence of double bonds in the ring
  • Due to the presence of nitrogen atoms

What is the catalyst used in the industrial synthesis of pyrrole from furans?

  • Alumina (correct)
  • Raney Ni
  • Nickel
  • Sulfuric acid

What type of reaction involves replacement of hydrogen or carbon dioxide from an acid in the mercuration of furan?

<p>Substitution reaction (A)</p> Signup and view all the answers

What does the formylation of furan involve?

<p>Gattermann Koch formylation (A)</p> Signup and view all the answers

What is Raney Ni composed mostly of?

<p>Nickel (A)</p> Signup and view all the answers

What is the strongest base required for the synthesis of furan from carbohydrates?

<p>NaOH (A)</p> Signup and view all the answers

In the synthesis of furan from carbohydrates, what is the first step?

<p>Distillation of CH with sulfuric acid (D)</p> Signup and view all the answers

Which statement about the properties of furan is correct?

<p>Furan has a boiling point of 31.4°C and is highly volatile at room temperature (A)</p> Signup and view all the answers

In electrophilic substitution reactions of furan, which position is primarily substituted?

<p>The 2-position (A)</p> Signup and view all the answers

What is the reason given for furan undergoing electrophilic substitution at the 2-position?

<p>Attack at the 2-position gives more resonance contributing structures (C)</p> Signup and view all the answers

What is the yield of furan reported by Wilson when furoic acid is heated to 200°C without a catalyst?

<p>78% (B)</p> Signup and view all the answers

What is the key factor that contributes to the aromaticity of furan?

<p>The presence of a planar ring structure with parallel p orbitals allowing for delocalization of electrons (B)</p> Signup and view all the answers

Which of the following is NOT a method for the industrial synthesis of furan?

<p>Acid-catalyzed dehydration of sucrose (B)</p> Signup and view all the answers

In the Paal-Knorr synthesis of furan, what type of reaction occurs?

<p>Cyclizing dehydration (C)</p> Signup and view all the answers

What is the role of the base in the Feist-Benary synthesis of furan?

<p>To remove a proton from the α-haloketone, generating an enolate (A)</p> Signup and view all the answers

Which of the following statements about furan is correct?

<p>Furan can act as a diene in Diels-Alder reactions due to the delocalization of electrons in the ring (A)</p> Signup and view all the answers

What is the primary medicinal use of furan derivatives?

<p>Anticancer drugs (B)</p> Signup and view all the answers

Which of the following statements about the aromaticity of furan is correct?

<p>Furan is aromatic because it has 6 delocalized pi electrons following Hückel's rule. (D)</p> Signup and view all the answers

In the Paal-Knorr synthesis of furan, what type of reaction occurs?

<p>Acid-catalyzed cyclizing dehydration reaction (A)</p> Signup and view all the answers

Which of the following is the correct mechanism for the Feist-Benary synthesis of furan?

<p>A base-catalyzed condensation reaction between an α-haloketone and a β-ketoester. (A)</p> Signup and view all the answers

Which of the following reactions is NOT a method for the industrial synthesis of furan?

<p>Acid-catalyzed dehydration of carbohydrates (A)</p> Signup and view all the answers

In electrophilic substitution reactions of furan, which position is primarily substituted?

<p>The 2-position (B)</p> Signup and view all the answers

Which of the following statements about the properties of furan is correct?

<p>Furan is a diene and can participate in Diels-Alder reactions. (C)</p> Signup and view all the answers

What is the primary reason for the preference of electrophilic substitution at the 2-position over the 3-position in furan?

<p>Substitution at the 2-position leads to a more stable resonance-stabilized intermediate. (B)</p> Signup and view all the answers

What is the primary reason for furan's solubility in most organic solvents but insolubility in ether?

<p>The aromatic nature of furan disrupts its ability to form dipole-dipole interactions with ether. (D)</p> Signup and view all the answers

In the synthesis of furan from carbohydrates, what is the role of the sulfuric acid in the first step?

<p>It acts as a dehydrating agent to remove water from the carbohydrate. (C)</p> Signup and view all the answers

Which of the following statements about the properties of furan is incorrect?

<p>Furan is soluble in water and most organic solvents. (D)</p> Signup and view all the answers

In the reaction reported by Wilson, where a 78% yield of furan was obtained from furoic acid at 200°C without a catalyst, what was the likely mechanism?

<p>Decarboxylation (D)</p> Signup and view all the answers

Which of the following statements best explains why furan undergoes electrophilic substitution reactions primarily at the 2-position?

<p>Substitution at the 2-position leads to a more stable resonance-stabilized intermediate. (D)</p> Signup and view all the answers

What is the key factor that enables furan to undergo Diels-Alder cycloaddition reactions?

<p>The high electronegativity of the oxygen atom reduces the aromaticity of furan. (A)</p> Signup and view all the answers

In the bromination of furan in the presence of alcohol, what is the mechanism for the formation of 2,5-dialkoxy-2,5-dihydrofurans?

<p>The alcohol acts as a nucleophile, adding to the C-5 position of the intermediate, followed by alcoholysis of the C-2 bromide. (B)</p> Signup and view all the answers

Which of the following is the primary reason for using Raney Ni as a reducing agent in the reduction of furan derivatives?

<p>Raney Ni is a fine-grained solid composed mostly of nickel, which provides a large surface area for the reduction to occur efficiently. (B)</p> Signup and view all the answers

In the industrial synthesis of pyrrole from furans, what is the primary role of the alumina catalyst?

<p>To promote the cycloaddition of furan with ammonia, forming the pyrrole ring. (A)</p> Signup and view all the answers

Which of the following statements best describes the Gattermann-Koch formylation of furan?

<p>It is a Vilsmeier-Haack type reaction that utilizes a formylating agent derived from an amine and a carbonyl compound. (D)</p> Signup and view all the answers

Which of the following reactions is NOT a common method for the synthesis of furan derivatives?

<p>Suzuki cross-coupling reactions involving furan-based boronic acids or esters. (B)</p> Signup and view all the answers
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