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Transcript:

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 451-482 Outline Notes by Dr. Allen D. Hunter, YSU Department of Chemistry, 2000. Outline 14A SECTION(S) 14.1/2/3 INTRODUCTION, NOMENCLATURE, AND PROPERTIES... 2 14B SECTION(S) 14.4 IMPORTANT CARBOXYLIC ACIDS... 7 14C SECTION(S) 18.2 AMINO ACIDS HAVING CARBOXYLIC ACID CONTAINING SIDE CHAINS... 8 14D SECTION(S) 17.2 BIOLOGICAL CARBOXYLIC ACIDS... 9 14E SECTION(S) 14.5 PREPARATION OF CARBOXYLIC ACIDS... 10 14F SECTION(S) 14.6/7 ACID/BASE CHEMISTRY... 11 14G SECTION(S)14.8/9 ESTERS... 13 14H SECTION(S)17.2 BIOLOGICAL ESTERS... 15 14I SECTION(S) 14.10/11 ESTER SYNTHESIS AND HYDROLYSIS... 16 14J SECTION(S) 14.12 PHOSPHOROUS ACIDS AND ESTERS... 21

Chemistry 506 Dr. Hunter s Class Chapter 14. 2 14A 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

Chemistry 506 Dr. Hunter s Class Chapter 14. Acid Chlorides 3 Anhydrides Amides (Chapter 15)

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

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

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

Chemistry 506 Dr. Hunter s Class Chapter 14. 14B 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

Chemistry 506 Dr. Hunter s Class Chapter 14. 8 14C 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

Chemistry 506 Dr. Hunter s Class Chapter 14. 14D Section(s) 17.2 Biological Carboxylic Acids 9 Fatty Acids R-CO 2 H

Chemistry 506 Dr. Hunter s Class Chapter 14. 10 14E Section(s) 14.5 Preparation of Carboxylic Acids Oxidation Reactions Oxidation of Aldehydes (Strong) Oxidation of 1 Alcohols (Strong)

Chemistry 506 Dr. Hunter s Class Chapter 14. 11 14F 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.

Chemistry 506 Dr. Hunter s Class Chapter 14. 12 Nomenclature of Carboxylate Salts Metal Alkanoate Examples Carboxylate Salts plus Acids HCl, H 2 SO 4, etc.

Chemistry 506 Dr. Hunter s Class Chapter 14. 13 14G 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

Chemistry 506 Dr. Hunter s Class Chapter 14. 14 Ethyl Acetate (Ethyl Ethanoate) IUPAC Nomenclature Alkyl Alkanoate Examples

Chemistry 506 Dr. Hunter s Class Chapter 14. 15 14H 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

Chemistry 506 Dr. Hunter s Class Chapter 14. 16 14I 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)

Chemistry 506 Dr. Hunter s Class Chapter 14. 17 Indirect Esterification (easier) Via Acid Chlorides (Thionyl Chloride, SOCl 2 ) and Alcohols Alkanoyl Chlorides

Chemistry 506 Dr. Hunter s Class Chapter 14. 18 Anhydride Routes to Esters Acetic Anhydride (only anhydride name for 506) Preparation via Acid Chloride plus Carboxylic Acid Anhydride plus Alcohol (easy)

Chemistry 506 Dr. Hunter s Class Chapter 14. 19 Synthesis of Polyester Condensation Polymers Dacron, etc. Used in Fibers, Pop bottles, etc. PET, Poly(ethylene terephthalate) Terephthalic Acid plus Ethylene Glycol

Chemistry 506 Dr. Hunter s Class Chapter 14. 20 Ester Hydrolysis Hydrolysis by H 3 O + Hydrolysis by OH - Soaponification Hydrolysis by lipase

Chemistry 506 Dr. Hunter s Class Chapter 14. 21 14J Section(s) 14.12 Phosphorous Acids and Esters H 3 PO 4 neutralization Stepwise addition of OH -

Chemistry 506 Dr. Hunter s Class Chapter 14. 22 H 3 PO 4 alkylation Addition of one equivalent of Alcohol Cf. Carboxylic Acid reactions Enzyme catalyzed gives monoalkyl phosphates Diesters and Triesters Questions 14.1-14.48

Chemistry 506 Dr. Hunter s Class Chapter 14. 23 Index of Topics and Vocabulary A Acetic Acid... 7 Acetic Anhydride... 18 Acid Chloride... 18 Acid Chlorides... 3, 17 Acid/Base Chemistry... 11 Alcohols... 17 Alkanoyl Chlorides... 17 Alkyl Alkanoate... 14 alkylation... 22 Amides... 3 Amino Acids... 8 Amino Acids having Carboxylic Acid Containing Side Chains... 8 Anhydride... 18 Anhydrides... 3 anoic acid... 6 Ants... 7 Aspartic Acid... 8 B Base... 11 Benzoic Acid... 7 Biological Carboxylic Acids... 9 Biological Esters... 15 Bp... 4, 13 C Carboxylate Salts... 12 Carboxylic Acid... 2, 18 Carboxylic Acids... 2, 6 Carboxylic Acids and Water... 11 Carboxylic Acids plus Bases... 11 CO 3-2... 11 Condensation Polymers... 19 Covalent Bonds... 4, 5 D Dacron... 19 Derivatives... 2 dicarboxylic acid... 7 Diesters... 22 Dipole - Dipole... 5 Directionally Specific... 4 DNA... 6 Doubling of MW... 6 E Electronegativity... 11 Ester Synthesis and Hydrolysis... 16 Esterification... 16, 17 Esters... 2, 13 Ethanoic Acid... 7 Ethyl Acetate... 14 Ethyl Ethanoate... 14 Ethylene Glycol... 19 F Fatty Acids... 9, 15 Fibers... 19 Formic Acid... 7 G Glutamic Acid... 8 Glycerol... 15 H H + catalyst... 16 H + /H 2 O... 16 H 2 SO 4... 12 H 3 O +... 16 H 3 PO 4... 21 H-bond Acceptors... 4 H-bond Donors... 4 H-bonding acceptor... 13 HCl... 12 HCO 3 -... 11 Hydrogen Bonded Dimers... 6 Hydrogen Bonding... 4 Hydrogen Bonds... 4, 5 Hydrogen-bonding... 13 Hydrolysis... 16, 20 Hydrolysis by H 3 O +... 20 Hydrolysis by lipase... 20 Hydrolysis by OH -... 20 I Important Carboxylic Acids... 7 Intermolecular Bonds... 5 Introduction, Nomenclature, and Properties... 2 Ionic Bonds... 5 IUPAC... 6, 14 L lipase... 20 Lone pairs... 4 M Metal Alkanoate... 12 Methanoic Acid... 7 monoalkyl phosphates... 22 Mp... 4,13 N Nomenclature... 6, 12, 14 NR 3... 11 O OH -... 11, 21 Oxalic Acid... 7 Oxidation of 1 Alcohols... 10 Oxidation of Aldehydes... 10 Oxidation Reactions... 10

Chemistry 506 Dr. Hunter s Class Chapter 14. 24 P Partial Charges... 13 PET... 19 Phosphorous Acids and Esters... 21 Physical Properties... 4, 13 Poly(ethylene terephthalate)... 19 Polyester... 19 Preparation of Carboxylic Acids... 10 Proteins... 8 Pyridine... 11 Q Questions... 22 R Relative Strengths of Intermolecular Bonds... 5 Rhubarb... 7 S Soaponification... 20 SOCl 2... 17 Spinach... 7 T Terephthalic Acid... 19 Thionyl Chloride... 17 Triesters... 22 Triglycerides... 15 V Van der Waals... 5 Vinegar... 7 d δ - 13 δ + 13

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