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Chapter 14 Carboxylic Acids, Esters, Amines, and Amides

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1 Chapter 14 Carboxylic Acids, Esters, Amines, and Amides
14.1 Carboxylic Acids

2 A poem by Ogden Nash The ant has made himself illustrious
Through constant industry industrious So what? Would you be calm and placid If you were full of formic acid?

3 Carboxylic Acids A carboxylic acid contains a carboxyl group, which
is a carbonyl group (C=O) attached to a hydroxyl group (—OH). is found on carbon 1 in carboxylic acids. hydroxyl group or CH3COOH carbonyl group

4 CH3—CH3 Ethane CH3—COOH Ethanoic acid
IUPAC Names In the IUPAC names of carboxylic acids the -e in the alkane name is replaced with -oic acid. CH Methane HCOOH Methanoic acid CH3—CH3 Ethane CH3—COOH Ethanoic acid substituents are numbered from the carboxyl carbon 1. 3-methylbutanoic acid

5 Names and Sources of Some Carboxylic Acids

6 Common Names for Acids HCOOH Formic Formica (ant)
CH3COOH Acetic Acetum (sour) CH3CH2COOH Propionic Pro (first) + Pion (fat) CH3(CH2)2COOH Butyric Butyrum (butter) CH3(CH2)3COOH Valeric Valere (strong) CH3(CH2)4COOH Caproic Caper (goat) CH3(CH2)5COOH Enanthic Vine (wine) CH3(CH2)6COOH Caprylic Caper (goat)

7 Common Carboxylic Acids
methanoic acid (formic acid) ethanoic acid (acetic acid)

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9 Aromatic Carboxylic Acids
Benzoic acid is the aromatic carboxylic acid. locates substituents by numbering the ring from carbon 1 in the carboxyl group. 3,4-Dichlorobenzoic Acid Benzoic Acid Para-Aminobenzoic Acid

10 Chapter 14 Carboxylic Acids, Esters, Amines, and Amides
14.2 Properties of Carboxylic Acids 10 10

11 Polarity of Carboxylic Acids
are strongly polar. have two polar groups: hydroxyl (−OH) and carbonyl (C=O). 11 11

12 Comparison of Boiling Points
Compound Molar Mass Boiling Point °C °C °C 12 12

13 Solubility in Water Carboxylic acids:
form hydrogen bonds with many water molecules. with 1-4 carbon atoms are very soluble in water. Water molecules 13 13

14 Acidity of Carboxylic Acids
are weak acids. ionize in water to produce carboxylate ions and hydronium ions. 14 14

15 Neutralization of Carboxylic Acids
Carboxylic acid salts are a product of the neutralization of a carboxylic acid with a strong base. CH3—COOH + NaOH CH3—COO– Na+ + H2O acetic acid sodium acetate (carboxylic acid salt) are used as preservatives and flavor enhancers. 15 15

16 Chapter 14 Carboxylic Acids, Esters, Amines, and Amides
14.3 Esters 16 16

17 Esters In an ester, the H in the carboxyl group is replaced
with an alkyl group. ester group 17 17

18 Esterification Esterification is the reaction of
a carboxylic acid and alcohol in the presence of an acid catalyst to produce an ester. Ethyl acetate (an ester) 18 18

19 Ester Products Aspirin
is used to relieve pain and reduce inflammation. is an ester of salicylic acid and acetic acid. Oil of wintergreen is used to soothe sore muscles. is an ester of salicylic acid and methanol. 19 19

20 Naming Esters The name of an ester contains the names of
the alkyl group from the alcohol. the carbon chain from the acid with –ate ending. methyl ethanoate (acetate) IUPAC: methyl ethanoate common: methyl acetate 20 20

21 Naming Esters Esters are named with the alkyl group of the alcohol,
and the salt (-ate) of the carboxylic acid From methanol (methyl alcohol) From ethanoic acid (acetic acid) Methyl ethanoate (methyl acetate) 21 21

22 Esters in Plants Esters give pleasant fragrances and flavors to many fruits and flowers. 22 22

23 Acid Hydrolysis of Esters
In acid hydrolysis an ester reacts with water to produce a carboxylic acid and an alcohol. an acid catalyst is required. O  H+ H—C—O—CH2—CH H2O  H—C—OH + H—O—CH2—CH3 23 23

24 Base Hydrolysis (Saponification)
Base hydrolysis or saponification, is the reaction of an ester with a strong base. produces the salt of the carboxylic acid and an alcohol. O || CH3—C—O—CH2—CH NaOH  CH3—C—O– Na+ + HO—CH2—CH3 salt of carboxylic acid alcohol 24 24

25 Base Hydrolysis of Fatty Acids Produces Soaps
25 25

26 Cleaning Action of Soap
A soap contains a nonpolar end that dissolves in nonpolar fats and oils, and a polar end that dissolves in water. forms groups of soap molecules called micelles that dissolve in water and are washed away. 26 26

27 Chapter 14 Carboxylic Acids, Esters, Amines, and Amides
14.4 Amines 27 27

28 Amines Amines are derivatives of ammonia, NH3.
contain N attached to one or more alkyl or aromatic groups. N H 2 28

29 Naming Amines Simple amines are named as alkylamines.
list the names of the alkyl groups bonded to the N atom in alphabetical order in front of amine. CH3—CH2—NH2 Ethylamine CH3—NH—CH3 Dimethylamine CH3 | CH3—N—CH2—CH3 Ethyldimethylamine 29 29

30 Do You ? N Know What

31 Aromatic Amines The amine of benzene is named aniline.
Alkyl groups on the N use the prefix N- with alkyl name. aniline chloroaniline N-methylaniline meta-chloroaniline 31 31

32 Hydrogen Bonding for Amines
The N−H bond provides hydrogen bonding in 1°and 2° amines, but not in 3° amines. is not as polar as the O-H bonds in alcohols. 32 32

33 Solubility in Water Amines with 1-6 carbon atoms are soluble in water.
form hydrogen bonds with the polar O-H bond in water. Copyright © by Pearson Education, Inc. 33 33

34 Amines React as Bases Like ammonia, amines are weak bases in water.
NH H2O NH OH– ammonium hydroxide CH3—NH H2O CH3—NH OH– methylammonium hydroxide 34 34

35 Neutralization Forms Amine Salts
An amine salt forms when an amine is neutralized by acid. is named by replacing the amine part of the name with ammonium, followed by the name of the negative ion. CH3—NH2 + HCl CH3—NH3+ Cl– methylamine methylammonium chloride 35 35

36 Properties of Amine Salts
Amine salts are solids at room temperature. soluble in water and body fluids. the form used for drugs. Ephedrine hydrochloride Ephedrine HCl Sudafed Diphenhydramine hydrochloride Diphenhydramine HCl Benadryl 36 36

37 Alkaloids Alkaloids are
physiologically active nitrogen-containing compounds. obtained from plants. used as anesthetics, antidepressants, and in stimulants such as caffeine. often addictive. 37 37

38 Cocaine Cocaine (from coca leaves ) is
sold illegally as the amine salt. reacted with NaOH to produce the free amine form known as “crack.” Cocaine hydrochloride Cocaine (free base) 38 38

39 Caffeine Caffeine is a stimulant of the central nervous system.
is found in coffee beans, tea, chocolate, and soft drinks. Caffeine 39 39

40 Nicotine Nicotine increases the adrenaline level in the blood.
causes addiction to tobacco. N C H 3 40

41 Morphine and Codeine Morphine and codeine are alkaloids.
obtained from the oriental poppy plant. used as painkillers. modified to make heroin. Morphine Codeine 41 41

42 Chapter 14 Carboxylic Acids, Esters, Amines, and Amides
14.5 Amides 42 42

43 Amides In amides, an amino group(–NH2) replaces the –OH group of carboxylic acids. 43 43

44 Aromatic Amide The aromatic amine is benzamide. Benzamide 44 44

45 Preparation of Amides Amides are produced
by reacting a carboxylic acid with ammonia or an amine (1° or 2°). using heat. O O  Heat  CH3—C—OH + NH CH3—C—NH2 + H2O O O  Heat  CH3—C—OH + CH3—NH CH3—C—NH—CH3 + H2O 45 45

46 Naming Amides Amides are named as alkanamides.
IUPAC replaces –oic acid ending with –amide. Common names replace -ic acid ending with –amide. Methanamide (IUPAC) Formamide (common) Propanamide (IUPAC) Propionamide (common) 46 46

47 Naming Amides with N Groups
An alkyl group bonded to the N atom is named as N-alkyl in front of the amide name. N-methylethanamide (IUPAC) N-methylacetamide (common) N-ethylpropanamide (IUPAC) N-ethylpropionamide (common) 47 47

48 Some Amides in Health and Medicine
Urea is the end product of protein metabolism. Saccharin is an artificial sweetener. Some amides such as phenobarbital, NembutalTM and SeconalTM are barbiturates. Acetaminophen is used to reduce fever and pain. 48 48

49 Some Amides in Health and Medicine
49 49

50 Physical Properties of Amides
that are primary (−NH2) or secondary (−NH−) form hydrogen bonds. that are primary have higher melting points than secondary. that are tertiary (no H on N) do not form hydrogen bonds and have lower melting points. all form hydrogen bonds with water. with 1-5 carbon atoms are soluble in water. 50 50

51 Hydrogen Bonding of Amides
|| CH3—C—N—H | H Hydrogen bonding occurs between primary amides. H 51 51

52 Hydrolysis of Amides Amides undergo
acid hydrolysis to produce a carboxylic acid and an ammonium salt. base hydrolysis to produce the salt of a carboxylic acid and an amine or ammonia. 52 52

53 Hydrolysis Reactions O || O CH3—C—OH + NH4+Cl– || HCl + H2O CH3—C—NH2
acid hydrolysis O || O CH3—C—OH + NH4+Cl– || HCl + H2O CH3—C—NH2 NaOH O CH3—C—O– Na+ + NH3 base hydrolysis 53 53

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