Interpretation:
To arrange the given amides in decreasing order of reactivity towards acid-catalyzed hydrolysis reaction.
Concept introduction:
The normal reaction of an amide with water does not give good yield of product. As amides are least reactive
The reaction of water and amides in presence of acid gives a carboxylic acid as a product. The reaction eqaution is written as,
The reactivity of amide also depends upon the leaving tendency of amine part from acyl group. The weaker the base better will be the leaving group. The basicity of
Want to see the full answer?
Check out a sample textbook solutionChapter 11 Solutions
Essential Organic Chemistry, Global Edition
- Predict the major products formed when the following amines undergo exhaustivemethylation, treatment with Ag2O, and heating.N-ethylpiperidinearrow_forwardWhat products are formed when all of the amide and ester bonds are hydrolyzed in each of the following compounds? Tamiflu [part (a)] is the trade name of the antiviral agent oseltamivir, thought to be the most effective agent in treating influenza. Aspartame [part (b)] is the artificial sweetener used in Equal and many diet beverages. One of the products of this hydrolysis reaction is the amino acid phenylalanine. Infants afflicted with phenylketonuria cannot metabolize this amino acid, so it accumulates, causing mental retardation. When the affliction is identified early, a diet limiting the consumption of phenylalanine (and compounds like aspartame that are converted to it) can make a normal life possible.arrow_forwardAmides undergo hydrolysis under acidic conditions to give Select one: O Carboxylate ion and ammonium ion Carboxylic acid and amine Carboxylate ion and amine Carboxylic acid and ammonium ionarrow_forward
- Draw the structure of the following three isomeric amides with chemical formula C6H11NO. Amide #1: (E)-N,N-dimethyl-2-butenamide Amide #2: (Z)-N-methyl-3-pentenamide Amide #3: (Z)-3-hexenamidearrow_forwardOxytocin, sold under the trade name Pitocin, is a naturally occurring hormone used to stimulate uterine contractions and induce labor. Classify each amide in oxytocin as 1°, 2°, or 3°. NH2 H2N NH HN 'N H2N NH NH2 S oxytocin но IZarrow_forwardDraw the structures for the carbonyl compound and amine required to synthesize benzyl methylamine via reductive amination. Lone pairs do not need to be included.arrow_forward
- Classify the amides in dolastatin, an anticancer compound isolated from the Indian seahare Dolabella auricularia, as 1°, 2°, or 3°.arrow_forwardOxytocin, sold under the trade name Pitocin, is a naturally occurring hormone used to stimulate uterine contractions and induce labor. Classify each amide in oxytocin as 1°, 2°, or 3°.arrow_forwardWhat products are formed when all of the amide and ester bonds arehydrolyzed in each of the following compounds? Tamiflu [part (a)] is the trade name of the antiviral agent oseltamivir, thought to be the most effective agent in treating influenza. Aspartame [part (b)] is the artificial sweetener used in Equal and many diet beverages. One of the products of this hydrolysis reaction is the amino acid phenylalanine. Infants afflicted with phenylketonuria cannot metabolize this amino acid, so it accumulates, causing mental retardation. When the affliction is identified early, a diet limiting the consumption of phenylalanine (and compounds like aspartame that are converted to it) can make a normal life possible.arrow_forward
- What products are formed when all of the amide and ester bonds are hydrolyzed in each of the following compounds? Tamiu [part (a)] is the trade name of the antiviral agent oseltamivir, thought to be the most effective agent in treating inuenza. Aspartame [part (b)] is the articial sweetener used in Equal and many diet beverages. One of the products ofthis hydrolysis reaction is the amino acid phenylalanine. Infants afflicted with phenylketonuria cannot metabolize this amino acid, so it accumulates, causing mental retardation. When the affliction is identied early, a diet limiting the consumption of phenylalanine (and compounds like aspartame that are converted to it) can make a normal life possible.arrow_forward- 11 3 1 8 12 Pregabalin (LyricaTM) H₂N Primary amine Primary amide Tertiary amine Secondary amine Secondary amide OHarrow_forwardSelect the name for each amide. ye N-ethylpropanamide N-methylbutanamide N-butylethanamide N-ethylbutanamide 4-cyclopentylbutanamide 5-cyclopentylpentanamide O cyclopentylbutanamide butanamide cyclopentane N-butylethanamide N-diethylacetamide N,N-diethylethanamide N,N-dimethylacetamide N-ethyl.N-methylbenzoate ON-ethyl,N-methyl-2-phenylpropanamide N-ethyl-N-methyl-2-phenylethanamide N,N-diethylbenzoatearrow_forward
- Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningGeneral, Organic, and Biological ChemistryChemistryISBN:9781285853918Author:H. Stephen StokerPublisher:Cengage Learning
- Organic And Biological ChemistryChemistryISBN:9781305081079Author:STOKER, H. Stephen (howard Stephen)Publisher:Cengage Learning,Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning