Textbook Question
The ester methyl butanoate has the odor and flavor of strawberries.
a. Draw the condensed structural formula for methyl butanoate.
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Ch.14 Carboxylic Acids, Esters, Amines, and Amides
Timberlake13th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9780134421353
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Table of contents
- Ch.1 Chemistry in Our Lives11
- Ch.2 Chemistry and Measurements80
- Ch.3 Matter and Energy54
- Ch.4 Atoms and Elements51
- Ch.5 Nuclear Chemistry42
- Ch.6 Ionic and Molecular Compounds57
- Ch.7 Chemical Quantities and Reactions41
- Ch.8 Gases29
- Ch.9 Solutions51
- Ch.10 Acids and Bases and Equilibrium65
- Ch.11 Introduction to Organic Chemistry: Hydrocarbons78
- Ch.12 Alcohols, Thiols, Ethers, Aldehydes, and Ketones83
- Ch.13 Carbohydrates54
- Ch.14 Carboxylic Acids, Esters, Amines, and Amides90
- Ch.15 Lipids61
- Ch.16 Amino Acids, Proteins, and Enzymes84
- Ch.17 Nucleic Acids and Protein Synthesis83
- Ch.18 Metabolic Pathways and ATP Production67
Timberlake13th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9780134421353Not the one you use?Change textbook
Chapter 14, Problem 46d
Draw the condensed structural or line-angle formulas for the products from the hydrolysis of each of the following amides with NaOH:
d. 
Verified step by step guidance1
Identify the functional group in the amide. Amides consist of a carbonyl group (C=O) directly bonded to a nitrogen atom (N). Hydrolysis of an amide involves breaking the bond between the carbonyl carbon and the nitrogen atom.
Understand the reaction conditions. Hydrolysis with NaOH (a strong base) results in the formation of a carboxylate ion (R-COO⁻) and an amine (R'-NH₂ or R'-NH depending on the structure of the amide).
Examine the structure of the given amide (from the image) to determine the R group attached to the carbonyl carbon and the R' group attached to the nitrogen atom. These groups will dictate the products of the reaction.
Write the products of the reaction. The carbonyl carbon will form a carboxylate ion (R-COO⁻) due to the reaction with NaOH, and the nitrogen atom will form an amine (R'-NH₂ or R'-NH). Represent these products using condensed structural formulas or line-angle formulas.
Ensure the products are balanced and consistent with the reaction mechanism. Verify that the number of atoms and charges are conserved in the reaction.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Hydrolysis of Amides
Hydrolysis of amides involves the reaction of an amide with water, often facilitated by a base like NaOH. This process breaks the amide bond, resulting in the formation of a carboxylic acid and an amine or ammonia. Understanding this reaction is crucial for predicting the products and their structures.
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Acidic Hydrolysis Concept 1
Condensed Structural Formula
A condensed structural formula provides a simplified representation of a molecule, showing the arrangement of atoms without depicting all the bonds explicitly. It is useful for visualizing the molecular structure and understanding functional groups. In the context of hydrolysis, it helps in illustrating the products formed from the reaction.
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1:53Condensed Formula Concept 1
Line-Angle Formula
The line-angle formula, or skeletal formula, is a shorthand representation of organic molecules where vertices represent carbon atoms and lines represent bonds. This format is particularly useful for depicting larger molecules clearly and efficiently. It allows chemists to quickly visualize the structure of the products resulting from the hydrolysis of amides.
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Related Practice
Textbook Question
Draw the condensed structural or line-angle formulas for the products from the hydrolysis of each of the following amides with HCl:
d.
Textbook Question
Draw the condensed structural or line-angle formulas for the products from the hydrolysis of each of the following amides with NaOH:
a.
1
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Textbook Question
Draw the condensed structural or line-angle formulas for the products from the hydrolysis of each of the following amides with NaOH:
c.
Textbook Question
Draw the condensed structural formulas and write the IUPAC names for two structural isomers of the carboxylic acids that have the molecular formula C4H8O2.
Textbook Question
The ester methyl butanoate has the odor and flavor of strawberries.
c. Write the balanced chemical equation for the acid hydrolysis of methyl butanoate.
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