Explain how the class I carbonyl compound reacts? What will be the product when ethylamine and propyl amine reacts with acetyl chloride? Why only one amide obtained after the reaction of acetyl chloride with a mixture of ethylamine and trimethylamine?

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter18: Functional Derivatives Of Carboxylic Acids
Section: Chapter Questions
Problem 18.59P
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Chapter 1 (Carbonyl compounds I)

  1. Explain how the class I carbonyl compound reacts?
  2. What will be the product when ethylamine and propyl amine reacts with acetyl chloride?
  3. Why only one amide obtained after the reaction of acetyl chloride with a mixture of ethylamine and trimethylamine?
  4. Excess amine is required in the reaction of acetyl chloride with amine whereas excess alcohol is not required in the reaction of acetyl chloride and alcohol. Why?
  5. List the following ester in order of decreasing reactivities towards hydrolysis with reason:

Methyl benzoate, p-nitro methyl benzoate and p-methoxy methyl benzoate

  1. The reaction of an ester with an amine is not as slow as the reaction of an ester with water or an alcohol. Explain with reason.
  2. Explain why the rate of aminolysis of an ester cannot be increased by H+, OH- or OR-.
  3. How can you activate the carboxylic acid?
  4. Is acid catalyzed hydrolysis of acetamide a reversible or an irreversible reaction. Explain.

Chapter 2 (Carbonyl compounds II)

  1. Write the product when ester of propionic acid reacts with excess of methyl magnesium bromide.
  2. Name the product when 2-methyl propionate undergoes reduction with sodium borohydride (NaBH4).
  3. Write the product when ethanoyl chloride reacts with NaBH4.
  4. Write the product when N-methylacetamide is reduced with LiAlH4/H2O.
  5. Explain the use of Wolff Kishner reduction.
  6. Explain reductive amination.

Chapter 3 (Carbonyl compound III)

  1. Explain the reaction for the formation of acetal and hemiacetal.
  2. Explain why N,N-disubstituted amide is less acidic than ester.
  3. Why only methyl ketone do undergoes haloform reaction.
  4. LDA is the base of choice for carbonyl compound to completely convert into enolate. Why?
  5. Explain the thermodynamic and kinetic product when 2-methyl cyclohexane is treated with methyl iodide in presence of LDA.
  6. Write the steps for Michael Addition reaction.
  7. Differentiate between Aldol and Claisen condensation reaction.

Chapter 4

  1. Define chemo selective reactions with examples.
  2. Write the reactant and product of Swern oxidation.
  3. Write the sequence of relative migratory aptitude of different group in Baeyer Villiger Oxidation.
  4. Write the different product obtained by the oxidation of alkene with potassium permanganate.

Chapter 5

  1. Explain why electrophilic aromatic substitution in Pyrrole takes place at C-2 positions whereas, in Pyridine it takes place at C-3 position.

Chapter 6

  1. Write the role of Corticosteroids in Pharmaceutical field.
  2. Write the rich source of Vitamin D. Write the metabolic pathway of Vitamin D to its most active form and which are the organ involved.
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