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Ch.14 Carboxylic Acids, Esters, Amines, and Amides
Timberlake - Chemistry: An Introduction to General, Organic, and Biological Chemistry 14th Edition
Timberlake14thChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9781292472249Not the one you use?Change textbook
All textbooksTimberlake 14thCh.14 Carboxylic Acids, Esters, Amines, and AmidesProblem 69a
Chapter 14, Problem 69a

Draw the condensed structural or line-angle formulas for the products of the following:
a. CH3–CH2–NH2 + H2O ⇌

Verified step by step guidance
1
Identify the type of reaction: This is an acid-base reaction where the amine group (CH₃―CH₂―NH₂) acts as a base and water (H₂O) acts as an acid.
Determine the role of each reactant: The lone pair of electrons on the nitrogen atom in CH₃―CH₂―NH₂ allows it to accept a proton (H⁺) from water, forming an ammonium ion.
Write the product of the reaction: When CH₃―CH₂―NH₂ accepts a proton, it forms CH₃―CH₂―NH₃⁺ (ethylammonium ion). Water, after donating a proton, becomes OH⁻ (hydroxide ion).
Express the equilibrium: The reaction is reversible, so the products are CH₃―CH₂―NH₃⁺ and OH⁻, and the equilibrium can be written as CH₃―CH₂―NH₂ + H₂O ⇌ CH₃―CH₂―NH₃⁺ + OH⁻.
Draw the condensed structural or line-angle formulas: Represent CH₃―CH₂―NH₂ as a condensed structure, and for the products, show CH₃―CH₂―NH₃⁺ (ethylammonium ion) and OH⁻ (hydroxide ion) in their respective forms.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Condensed Structural Formula

A condensed structural formula is a way of representing a chemical compound that shows the arrangement of atoms and the connectivity between them without depicting all the bonds explicitly. It typically groups atoms together to indicate how they are bonded, making it easier to visualize the structure of organic molecules. For example, CH₃―CH₂―NH₂ indicates a chain of carbon atoms with attached functional groups.
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Line-Angle Formula

The line-angle formula, also known as the skeletal formula, is a simplified representation of organic molecules where vertices represent carbon atoms and lines represent bonds. This method omits hydrogen atoms attached to carbons, making it easier to visualize complex structures. It is particularly useful for depicting larger molecules and their functional groups in a clear and concise manner.
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Acid-Base Reaction

An acid-base reaction involves the transfer of protons (H⁺ ions) between reactants, leading to the formation of new products. In the context of the given question, the amine (CH₃―CH₂―NH₂) can act as a base, while water (H₂O) can act as an acid, resulting in the formation of an ammonium ion and hydroxide ion. Understanding this concept is crucial for predicting the products of the reaction.
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Related Practice
Textbook Question

Draw the condensed structural or line-angle formula if cyclic, for each of the following:

b. cyclohexylamine

Textbook Question

Draw the condensed structural or line-angle formula if cyclic, for each of the following:

d. N-propylaniline

Textbook Question

Draw the condensed structural or line-angle formula if cyclic, for each of the following:

d. ethylmethylammonium bromide

Textbook Question

Draw the condensed structural formulas for the products of the reaction of aspartate and α-ketoglutarate which is catalyzed by aspartate transaminase (AST).

Textbook Question

Write the IUPAC name for each of the following:

b .

Textbook Question

Draw the condensed structural or line-angle formulas for the products from the hydrolysis of each of the following:

a.