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General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.1 Chapter 18 Amines and Amides 18.2 Properties of Amines
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General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.2 Boiling Points of Amines, Alcohols, and Alkanes The boiling points of amines are higher than alkanes of similar mass lower than alcohols of similar mass
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General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.3 Hydrogen Bonding in Amines The polar N—H bond provides hydrogen bonding in 1° and 2° amines but not 3° amines is not as polar as the —OH in alcohols
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General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.4 Solubility in Water Amines are soluble in water if they have 1 to 5 carbon atoms because the N atom in smaller amines forms hydrogen bonds with the polar O—H bond in water
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General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.5 Learning Check Consider the following compounds: 1) CH 3 —CH 2 —CH 2 —NH 2 2) CH 3 —CH 2 —NH—CH 3 3) CH 3 —CH 2 —CH 2 —CH 3 A. Which compound has the highest boiling point? B. Which compound(s) is (are) soluble in water?
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General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.6 Solution Consider the following compounds: 1) CH 3 —CH 2 —CH 2 —NH 2 2) CH 3 —CH 2 —NH—CH 3 3) CH 3 —CH 2 —CH 2 —CH 3 A. Which compound has the highest boiling point? 1) CH 3 —CH 2 —CH 2 —NH 2 B. Which compound(s) is(are) soluble in water? 1) CH 3 —CH 2 —CH 2 —NH 2 2) CH 3 —CH 2 —NH—CH 3
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General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.7 Amines are Brønsted-Lowry bases that attract a H + from H 2 O to the N atom weak bases in water Amines React as Bases
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General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.8 An amine salt forms when an amine is neutralized by an acid is named by replacing the amine part of the name with ammonium followed by the name of the negative ion Neutralization Forms Amine Salts
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General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.9 Properties of Amine Salts Amine salts are solids at room temperature soluble in water and body fluids the form used for drugs
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General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.10 Cocaine is sold illegally as an amine salt is reacted with NaOH to produce the free amine form known as “crack”
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General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.11 Learning Check Write the equation for ethylamine when it reacts with each of the following: A. H 2 O B. HCl
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General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.12 Solution Write the equation for ethylamine when it reacts with each of the following: A. B.
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