Chapter 21 The Chemistry of Carboxylic Acid Deriva7ves
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1 Organic Chemistry, 5th ed. Marc Loudon Chapter 21 The Chemistry of Carboxylic Acid Deriva7ves Eric J. Kantorowski California Polytechnic State University San Luis Obispo, CA
2 Chapter 21 Overview 21.1 Nomenclature and Classifica5on of Carboxylic Acid Deriva5ves 21.2 Structures of Carboxylic Acid Deriva5ves 21.3 Physical Proper5es of Carboxylic Acid Deriva5ves 21.4 Spectroscopy of Carboxylic Acid Deriva5ves 21.5 Basicity of Carboxylic Acid Deriva5ves 21.6 Introduc5on to Reac5ons of Carboxylic Acid Deriva5ves 21.7 Hydrolysis of Carboxylic Acid Deriva5ves 21.8 Reac5ons of Carboxylic Acid Deriva5ves with Nucleophiles 21.9 Reduc5on of Carboxylic Acid Deriva5ves 2
3 Chapter 21 Overview Reac5ons of Carboxylic Acid Deriva5ves with Organometallic Reagents Synthesis of Carboxylic Acid Deriva5ves Use and Occurrence of Carboxylic Acids and Their Deriva5ves 3
4 Carboxylic Acid Deriva8ves A carboxylic acid deriva8ve is a compound that can be hydrolyzed under acidic of basic condi5ons to give the related carboxylic acid 21.1 Nomenclature and Classifica7on of Carboxylic Acid Deriva7ves 4
5 Structures of Carboxylic Acid Deriva8ves 21.1 Nomenclature and Classifica7on of Carboxylic Acid Deriva7ves 5
6 Esters and Lactones 21.1 Nomenclature and Classifica7on of Carboxylic Acid Deriva7ves 6
7 Esters and Lactones Cyclic esters are called lactones The name is derived from the acid with the same number of carbons in the principle chain The ring size is denoted by a Greek leuer indica5ng the point of auachment 21.1 Nomenclature and Classifica7on of Carboxylic Acid Deriva7ves 7
8 Acid Halides Replace the ic ending with yl followed by the name of the halide 21.1 Nomenclature and Classifica7on of Carboxylic Acid Deriva7ves 8
9 Anhydrides The name is the parent acid is followed by anhydride 21.1 Nomenclature and Classifica7on of Carboxylic Acid Deriva7ves 9
10 Nitriles Drop the ic or oic ending and add onitrile The nitrile carbon counts as part of the chain length 21.1 Nomenclature and Classifica7on of Carboxylic Acid Deriva7ves 10
11 Amides, Lactams, and Imides Replace the ic or oic and add amide 21.1 Nomenclature and Classifica7on of Carboxylic Acid Deriva7ves 11
12 Amides, Lactams, and Imides Amides are classified according to the number of hydrogens on the amide nitrogen Use N for subs5tuents on the nitrogen 21.1 Nomenclature and Classifica7on of Carboxylic Acid Deriva7ves 12
13 Amides, Lactams, and Imides Cyclic amides are called lactams The nomenclature follows that of lactones 21.1 Nomenclature and Classifica7on of Carboxylic Acid Deriva7ves 13
14 Amides, Lactams, and Imides Imides are the nitrogen analogs of anhydrides Cyclic imides are of greater importance than open chain imides 21.1 Nomenclature and Classifica7on of Carboxylic Acid Deriva7ves 14
15 Nomenclature of Subs8tuent Groups The priori5es for ci5ng principle groups in a carboxylic acid deriva5ve are: 21.1 Nomenclature and Classifica7on of Carboxylic Acid Deriva7ves 15
16 Nomenclature of Subs8tuent Groups 21.1 Nomenclature and Classifica7on of Carboxylic Acid Deriva7ves 16
17 Carbonic Acid Deriva8ves Esters of carbonic acid are named like any other ester Other important deriva5ves include: 21.1 Nomenclature and Classifica7on of Carboxylic Acid Deriva7ves 17
18 Structures of Carboxylic Acid Deriva8ves The deriva5ves are very similar to other carbonyl compounds (bond lengths, angles) 21.2 Structures of Carboxylic Acid Deriva7ves 18
19 Structures of Carboxylic Acid Deriva8ves Because of the trigonal planar geometry at nitrogen, E and Z conformers are possible The interconversion is rela5vely rapid at room temperature (~10 s 1, E barrier 71 kj mol 1 ) 21.2 Structures of Carboxylic Acid Deriva7ves 19
20 Esters Polar; H bond acceptors only Typically vola5le, fragrant liquids Most are insoluble in water 21.3 Physical Proper7es of Carboxylic Acid Deriva7ves 20
21 Anhydrides and Acid Chlorides Lower anhydrides and acid chlorides are dense, water insoluble liquids Typically have acrid, piercing odors 21.3 Physical Proper7es of Carboxylic Acid Deriva7ves 21
22 Nitriles Highly polar (3.4 D for H 3 C C N) Nitriles larger than propionitrile are waterinsoluble Acetonitrile is a useful polar, apro5c solvent 21.3 Physical Proper7es of Carboxylic Acid Deriva7ves 22
23 Amides Polar with high boiling points Lower amides are water soluble Tend to aggregate due to H bonding 21.3 Physical Proper7es of Carboxylic Acid Deriva7ves 23
24 IR Spectroscopy 21.4 Spectroscopy of Carboxylic Acid Deriva7ves 24
25 IR Spectroscopy: Esters C=O stretch: cm 1 Readily dis5nguishes them from carboxylic acids, aldehydes, and ketones 21.4 Spectroscopy of Carboxylic Acid Deriva7ves 25
26 IR Spectroscopy: Anhydrides Two C=O stretches (also common for acid chlorides) Due to symmetric and asymmetric stretching 21.4 Spectroscopy of Carboxylic Acid Deriva7ves 26
27 IR Spectroscopy: Amides C=O stretch: cm 1 Much lower than other C=O stretches 21.4 Spectroscopy of Carboxylic Acid Deriva7ves 27
28 Primary, secondary, and ter5ary amides may also be differen5ated IR Spectroscopy: Amides 21.4 Spectroscopy of Carboxylic Acid Deriva7ves 28
29 IR Spectroscopy: Nitriles C N stretch: cm 1 Normally much stronger than C C stretch due to the large bond dipole 21.4 Spectroscopy of Carboxylic Acid Deriva7ves 29
30 1 H NMR Spectroscopy α Hydrogens next to carbonyl: δ Hydrogens on carbon next to alkoxy O: ~+0.6 ppm more than for that of alcohols and ethers 21.4 Spectroscopy of Carboxylic Acid Deriva7ves 30
31 1 H NMR Spectroscopy Amides display non equivalency for the two groups auached to the nitrogen They are diastereotopic Although these rotate at ~10 s 1, on the NMR 5me scale these groups appear frozen in posi5on 21.4 Spectroscopy of Carboxylic Acid Deriva7ves 31
32 C=O: δ C NMR Spectroscopy C N: δ Spectroscopy of Carboxylic Acid Deriva7ves 32
33 Basicity of Carboxylic Acid Deriva8ves Like carboxylic acids, their deriva5ves are also weakly basic Protona5on occurs on the carbonyl oxygen 21.5 Basicity of Carboxylic Acid Deriva7ves 33
34 Basicity of Carboxylic Acid Deriva8ves Amides are considerably more basic Nitriles are extremely weak bases 21.5 Basicity of Carboxylic Acid Deriva7ves 34
35 Reac8ons of Carboxylic Acid Deriva8ves There are three general categories: 1. Reac5ons at the carbonyl (or cyano) group a. at the C=O oxygen or C N nitrogen b. at the C=O carbon or C N carbon 2. Reac5ons involving the α carbon 3. Reac5ons at the nitrogen of amides 21.6 Introduc7on to the Reac7ons of Carboxylic Acid Deriva7ves 35
36 Reac8ons of Carboxylic Acid Deriva8ves Acyl subs8tu8on: Subs5tu5on at the carbonyl Addi7on is a typical reac5on of nitriles 21.6 Introduc7on to the Reac7ons of Carboxylic Acid Deriva7ves 36
37 Saponifica8on Hydrolysis of Esters Saponifica5on is effec5vely irreversible Classified as a nucleophilic acyl subs8tu8on 21.7 Hydrolysis of Carboxylic Acid Deriva7ves 37
38 Hydrolysis of Esters 21.7 Hydrolysis of Carboxylic Acid Deriva7ves 38
39 Hydrolysis of Esters Acid catalyzed hydrolysis The reac5on is slow and requires an excess of water 21.7 Hydrolysis of Carboxylic Acid Deriva7ves 39
40 Hydrolysis of Esters Classified as a nucleophilic acyl subs8tu8on 21.7 Hydrolysis of Carboxylic Acid Deriva7ves 40
41 Hydrolysis and Forma8on of Lactones 21.7 Hydrolysis of Carboxylic Acid Deriva7ves 41
42 Hydrolysis of Amides 21.7 Hydrolysis of Carboxylic Acid Deriva7ves 42
43 Hydrolysis of Nitriles More extreme condi5ons are required compared to those of esters and amides 21.7 Hydrolysis of Carboxylic Acid Deriva7ves 43
44 Hydrolysis of Nitriles Imidic acids can be viewed as the nitrogenanalogs of enols 21.7 Hydrolysis of Carboxylic Acid Deriva7ves 44
45 Hydrolysis of Nitriles Base promoted hydrolysis is also possible 21.7 Hydrolysis of Carboxylic Acid Deriva7ves 45
46 Hydrolysis of Acid Chlorides and Anhydrides Both react rapidly with water 21.7 Hydrolysis of Carboxylic Acid Deriva7ves 46
47 Nucleophilic Acyl Subs8tu8on Reac8ons The condi7ons for hydrolysis for these deriva5ves can differ considerably 21.7 Hydrolysis of Carboxylic Acid Deriva7ves 47
48 Nucleophilic Acyl Subs8tu8on Reac8ons 21.7 Hydrolysis of Carboxylic Acid Deriva7ves 48
49 Nucleophilic Acyl Subs8tu8on Reac8ons Energies in the reac5on coordinate diagram are affected by: Stability of the carbonyl compound The leaving group ability of X: 21.7 Hydrolysis of Carboxylic Acid Deriva7ves 49
50 Nucleophilic Acyl Subs8tu8on Reac8ons 21.7 Hydrolysis of Carboxylic Acid Deriva7ves 50
51 Reac8ons of Acid Chlorides with Nucleophiles 21.8 Reac7ons of Carboxylic Acid Deriva7ves with Nucleophiles 51
52 Reac8ons of Acid Chlorides with Nucleophiles 21.8 Reac7ons of Carboxylic Acid Deriva7ves with Nucleophiles 52
53 Reac8ons of Acid Chlorides with Nucleophiles Related reac5ons of sulfonyl chlorides 21.8 Reac7ons of Carboxylic Acid Deriva7ves with Nucleophiles 53
54 Reac8ons of Anhydrides with Nucleophiles 21.8 Reac7ons of Carboxylic Acid Deriva7ves with Nucleophiles 54
55 Reac8ons of Esters with Nucleophiles Transesterifica8on: 21.8 Reac7ons of Carboxylic Acid Deriva7ves with Nucleophiles 55
56 Reduc8on of Esters to Primary Alcohols 21.9 Reduc7on of Carboxylic Acid Deriva7ves 56
57 Reduc8on of Amides to Amines Note that a protonolysis step with aqueous acid follows the LiAlH 4 reduc5on This is followed by base to free the amine 21.9 Reduc7on of Carboxylic Acid Deriva7ves 57
58 Reduc8on of Amides to Amines Note how the amide reduc5on differs from that of ester reduc5on 21.9 Reduc7on of Carboxylic Acid Deriva7ves 58
59 Reduc8on of Amides to Amines 21.9 Reduc7on of Carboxylic Acid Deriva7ves 59
60 Reduc8on of Amides to Amines 21.9 Reduc7on of Carboxylic Acid Deriva7ves 60
61 Reduc8on of Nitriles to Primary Amines Two successive nucleophilic addi5ons occur 21.9 Reduc7on of Carboxylic Acid Deriva7ves 61
62 Reduc8on of Nitriles to Primary Amines 21.9 Reduc7on of Carboxylic Acid Deriva7ves 62
63 Reduc8on of Acid Chlorides to Aldehydes The Rosenmund reduc8on: 21.9 Reduc7on of Carboxylic Acid Deriva7ves 63
64 Reduc8on of Acid Chlorides to Aldehydes Use of deriva5ves of LiAlH 4 : 21.9 Reduc7on of Carboxylic Acid Deriva7ves 64
65 Rela8ve Reac8vi8es 21.9 Reduc7on of Carboxylic Acid Deriva7ves 65
66 Reac8ons of Esters with Grignard Reagents Reac7ons of Carboxylic Acid Deriva7ves with Organometallic Reagents 66
67 Reac8ons of Acid Chlorides with R 2 CuLi Dialkylcuprates are less reac5ve than Grignard reagents Reac7ons of Carboxylic Acid Deriva7ves with Organometallic Reagents 67
68 Summary of C.A. Deriva8ve Prepara8on Synthesis of esters: Acid catalyzed esterifica5on of RCO 2 H Alkyla5on of RCO 2 H or RCO 2 Acid chlorides or anhydrides with ROH Transesterifica5on Synthesis of acid chlorides: RCO 2 H with SOCl 2 or PCl Synthesis of Carboxylic Acid Deriva7ves 68
69 Summary of C.A. Deriva8ve Prepara8on Synthesis of anhydrides: RCO 2 H with dehydra5ng agents Acid chlorides with RCO 2 Synthesis of amides: Acid chlorides, anhydrides, or esters with amines Synthesis of Carboxylic Acid Deriva7ves 69
70 Summary of C.A. Deriva8ve Prepara8on Synthesis of nitriles: Cyanohydrin forma5on S N 2 reac5on of cyanide ion with alkyl halides or sulfonate esters Synthesis of Carboxylic Acid Deriva7ves 70
71 Nylon and Polyesters Nylon is a generic name given to polyamides Use and Occurrence of Carboxylic Acids and Their Deriva7ves 71
72 Nylon and Polyesters Polyesters are condensa8on polymers derived from diols and dicarboxylic acids Use and Occurrence of Carboxylic Acids and Their Deriva7ves 72
73 Waxes, Fats, and Phospholipids A wax is an ester of a fauy acid and a fauy alcohol A fat is derived form a molecule of glycerol and three molecules of fauy acid Use and Occurrence of Carboxylic Acids and Their Deriva7ves 73
74 Waxes, Fats, and Phospholipids Fats with no double bonds are called saturated fats Fats containing double bonds are called unsaturated fats Treatment of fats with KOH or NaOH gives glycerol and the salt of the fauy acid (a soap) This reac5on is the origin of the term saponifica8on Use and Occurrence of Carboxylic Acids and Their Deriva7ves 74
75 Waxes, Fats, and Phospholipids Phospholipids are also esters of glycerol The key structural difference is the presence of a polar phosphoric acid deriva5ve Use and Occurrence of Carboxylic Acids and Their Deriva7ves 75
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