Chemistry 506: Allied Health Chemistry 2. Chapter 14: Carboxylic Acids and Esters. Functional Groups with Single & Double Bonds to Oxygen
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1 Chemistry 506 Dr. Hunter s Class Chapter 14. Chemistry 506: Allied Health Chemistry 2 1 Chapter 14: Carboxylic Acids and Esters Functional Groups with Single & Double Bonds to Oxygen Introduction to General, Organic & Biochemistry, 5 th Edition by Bettelheim and March: Chapter 12, Pages Outline Notes by Dr. Allen D. Hunter, YSU Department of Chemistry, Outline 14A SECTION(S) 14.1/2/3 INTRODUCTION, NOMENCLATURE, AND PROPERTIES B SECTION(S) 14.4 IMPORTANT CARBOXYLIC ACIDS C SECTION(S) 18.2 AMINO ACIDS HAVING CARBOXYLIC ACID CONTAINING SIDE CHAINS D SECTION(S) 17.2 BIOLOGICAL CARBOXYLIC ACIDS E SECTION(S) 14.5 PREPARATION OF CARBOXYLIC ACIDS F SECTION(S) 14.6/7 ACID/BASE CHEMISTRY G SECTION(S)14.8/9 ESTERS H SECTION(S)17.2 BIOLOGICAL ESTERS I SECTION(S) 14.10/11 ESTER SYNTHESIS AND HYDROLYSIS J SECTION(S) PHOSPHOROUS ACIDS AND ESTERS... 21
2 Chemistry 506 Dr. Hunter s Class Chapter A Section(s) 14.1/2/3 Introduction, Nomenclature, and Properties Generic Structure of Carboxylic Acid and Carboxylic Acid Derivatives Members of this Class Carboxylic Acids Esters
3 Chemistry 506 Dr. Hunter s Class Chapter 14. Acid Chlorides 3 Anhydrides Amides (Chapter 15)
4 Chemistry 506 Dr. Hunter s Class Chapter 14. Physical Properties 4 Mp and Bp taste and feel Hydrogen Bonding H-bond Donors O-H and N-H H-bond Acceptors Lone pairs of O, N, and S Directionally Specific Hydrogen Bonds and Covalent Bonds
5 Chemistry 506 Dr. Hunter s Class Chapter 14. Relative Strengths of Intermolecular Bonds 5 Van der Waals < Dipole - Dipole < Hydrogen Bonds < Covalent Bonds Ionic Bonds
6 Chemistry 506 Dr. Hunter s Class Chapter 14. Hydrogen Bonded Dimers of Carboxylic Acids 6 Apparent Doubling of MW Cf. DNA IUPAC Nomenclature of Carboxylic Acids anoic acid (two words) Examples
7 Chemistry 506 Dr. Hunter s Class Chapter B Section(s) 14.4 Important Carboxylic Acids 7 Formic Acid (Methanoic Acid) Ants Acetic Acid (Ethanoic Acid) Vinegar Oxalic Acid (dicarboxylic acid) Rhubarb, Spinach, etc. Benzoic Acid
8 Chemistry 506 Dr. Hunter s Class Chapter C Section(s) 18.2 Amino Acids having Carboxylic Acid Containing Side Chains Amino Acids (Building Blocks of Proteins) Generic AA = H 2 N-CHR-CO 2 H Aspartic Acid (acidic) R = CH 2 C(=O)-OH Glutamic Acid (acidic) R = CH 2 CH 2 C(=O)-OH
9 Chemistry 506 Dr. Hunter s Class Chapter D Section(s) 17.2 Biological Carboxylic Acids 9 Fatty Acids R-CO 2 H
10 Chemistry 506 Dr. Hunter s Class Chapter E Section(s) 14.5 Preparation of Carboxylic Acids Oxidation Reactions Oxidation of Aldehydes (Strong) Oxidation of 1 Alcohols (Strong)
11 Chemistry 506 Dr. Hunter s Class Chapter F Section(s) 14.6/7 Acid/Base Chemistry Equilibrium of Carboxylic Acids and Water Effects of the Electronegativity of R Carboxylic Acids plus Bases Base = OH -, CO 3-2, HCO 3 -, NR 3, Pyridine, etc.
12 Chemistry 506 Dr. Hunter s Class Chapter Nomenclature of Carboxylate Salts Metal Alkanoate Examples Carboxylate Salts plus Acids HCl, H 2 SO 4, etc.
13 Chemistry 506 Dr. Hunter s Class Chapter G Section(s) 14.8/9 Esters Generic Structure Partial Charges on Carbon (δ + )and Oxygen (δ - ) No Hydrogen-bonding with self H-bonding acceptor Physical Properties Mp and Bp Cf. Carboxylic Acids odor
14 Chemistry 506 Dr. Hunter s Class Chapter Ethyl Acetate (Ethyl Ethanoate) IUPAC Nomenclature Alkyl Alkanoate Examples
15 Chemistry 506 Dr. Hunter s Class Chapter H Section(s) 17.2 Biological Esters Triglycerides Glycerol and Fatty Acids H H C O O C R H C O O C O R H C H O C R
16 Chemistry 506 Dr. Hunter s Class Chapter I Section(s) 14.10/11 Ester Synthesis and Hydrolysis Direct Esterification Uses H + catalyst Direct Hydrolysis Uses H 3 O + (i.e., H + /H 2 O)
17 Chemistry 506 Dr. Hunter s Class Chapter Indirect Esterification (easier) Via Acid Chlorides (Thionyl Chloride, SOCl 2 ) and Alcohols Alkanoyl Chlorides
18 Chemistry 506 Dr. Hunter s Class Chapter Anhydride Routes to Esters Acetic Anhydride (only anhydride name for 506) Preparation via Acid Chloride plus Carboxylic Acid Anhydride plus Alcohol (easy)
19 Chemistry 506 Dr. Hunter s Class Chapter Synthesis of Polyester Condensation Polymers Dacron, etc. Used in Fibers, Pop bottles, etc. PET, Poly(ethylene terephthalate) Terephthalic Acid plus Ethylene Glycol
20 Chemistry 506 Dr. Hunter s Class Chapter Ester Hydrolysis Hydrolysis by H 3 O + Hydrolysis by OH - Soaponification Hydrolysis by lipase
21 Chemistry 506 Dr. Hunter s Class Chapter J Section(s) Phosphorous Acids and Esters H 3 PO 4 neutralization Stepwise addition of OH -
22 Chemistry 506 Dr. Hunter s Class Chapter H 3 PO 4 alkylation Addition of one equivalent of Alcohol Cf. Carboxylic Acid reactions Enzyme catalyzed gives monoalkyl phosphates Diesters and Triesters Questions
23 Chemistry 506 Dr. Hunter s Class Chapter Index of Topics and Vocabulary A Acetic Acid... 7 Acetic Anhydride Acid Chloride Acid Chlorides... 3, 17 Acid/Base Chemistry Alcohols Alkanoyl Chlorides Alkyl Alkanoate alkylation Amides... 3 Amino Acids... 8 Amino Acids having Carboxylic Acid Containing Side Chains... 8 Anhydride Anhydrides... 3 anoic acid... 6 Ants... 7 Aspartic Acid... 8 B Base Benzoic Acid... 7 Biological Carboxylic Acids... 9 Biological Esters Bp... 4, 13 C Carboxylate Salts Carboxylic Acid... 2, 18 Carboxylic Acids... 2, 6 Carboxylic Acids and Water Carboxylic Acids plus Bases CO Condensation Polymers Covalent Bonds... 4, 5 D Dacron Derivatives... 2 dicarboxylic acid... 7 Diesters Dipole - Dipole... 5 Directionally Specific... 4 DNA... 6 Doubling of MW... 6 E Electronegativity Ester Synthesis and Hydrolysis Esterification... 16, 17 Esters... 2, 13 Ethanoic Acid... 7 Ethyl Acetate Ethyl Ethanoate Ethylene Glycol F Fatty Acids... 9, 15 Fibers Formic Acid... 7 G Glutamic Acid... 8 Glycerol H H + catalyst H + /H 2 O H 2 SO H 3 O H 3 PO H-bond Acceptors... 4 H-bond Donors... 4 H-bonding acceptor HCl HCO Hydrogen Bonded Dimers... 6 Hydrogen Bonding... 4 Hydrogen Bonds... 4, 5 Hydrogen-bonding Hydrolysis... 16, 20 Hydrolysis by H 3 O Hydrolysis by lipase Hydrolysis by OH I Important Carboxylic Acids... 7 Intermolecular Bonds... 5 Introduction, Nomenclature, and Properties... 2 Ionic Bonds... 5 IUPAC... 6, 14 L lipase Lone pairs... 4 M Metal Alkanoate Methanoic Acid... 7 monoalkyl phosphates Mp... 4,13 N Nomenclature... 6, 12, 14 NR O OH , 21 Oxalic Acid... 7 Oxidation of 1 Alcohols Oxidation of Aldehydes Oxidation Reactions... 10
24 Chemistry 506 Dr. Hunter s Class Chapter P Partial Charges PET Phosphorous Acids and Esters Physical Properties... 4, 13 Poly(ethylene terephthalate) Polyester Preparation of Carboxylic Acids Proteins... 8 Pyridine Q Questions R Relative Strengths of Intermolecular Bonds... 5 Rhubarb... 7 S Soaponification SOCl Spinach... 7 T Terephthalic Acid Thionyl Chloride Triesters Triglycerides V Van der Waals... 5 Vinegar... 7 d δ - 13 δ + 13
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