Chemistry 506: Allied Health Chemistry 2. Chapter 15: Amines and Amides. Functional Groups with Single Bonds to Nitrogen

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Chemistry 506 Dr. Hunter s Class Chapter 15. Chemistry 506: Allied Health Chemistry 2 1 Chapter 15: Amines and Amides Functional Groups with Single Bonds to Nitrogen Introduction to General, Organic & Biochemistry, 5 th Edition by Bettelheim and March: Chapter 15, Pages 483-514 Outline Notes by Dr. Allen D. Hunter, YSU Department of Chemistry, 2000. Outline 15A SECTION(S) 15.1/2/3 AMINES... 2 15B SECTION(S) 18.2 AMINO ACIDS HAVING AMINE/HETEROCYCLIC CONTAINING SIDE CHAINS... 8 15C SECTION(S) 15.4 AMINE BASICITY... 9 15D SECTION(S) 15.5/6 AMIDES... 12 15E SECTION(S) 15.7/8 AMIDE REACTIONS... 14 15F SECTION(S) 18.2 AMINO ACIDS HAVING AMIDE CONTAINING SIDE CHAINS... 17

Chemistry 506 Dr. Hunter s Class Chapter 15. 15A Section(s) 15.1/2/3 Amines 2 Amine Classification Ammonia 1, Primary Amine 2, Secondary Amine

Chemistry 506 Dr. Hunter s Class Chapter 15. 3, Tertiary Amine 3 4, Quaternary Ammonium Salts

Chemistry 506 Dr. Hunter s Class Chapter 15. IUPAC Nomenclature 4 Named as Alkyl Amines (multiple words) Dimethyl Amine Methyl Ethyl Amine Tetramethyl Ammonium Chloride

Chemistry 506 Dr. Hunter s Class Chapter 15. Aromatic Amines 5 Aniline (coal tar) N-methyl-N-ethyl aniline

Chemistry 506 Dr. Hunter s Class Chapter 15. Heterocyclic Amines 6 Pyridine (C 5 H 5 N, coal tar) Piperidine (C 5 H 11 N) Pyrimidine (1,3-C 4 H 4 N 2 ) Pyrole (C 4 H 5 N) Pyrrolidine (C 4 H 9 N)

Chemistry 506 Dr. Hunter s Class Chapter 15. Properties 7 Relatively high Mp and Bp Polar Hydrogen Bonding Donor Hydrogen Bonding Acceptor Solubility Stench! Putrescine H 2 N-(CH 2 ) 4 -NH 2 Cadaverine H 2 N-(CH 2 ) 5 -NH 2 Hydrogen Bonding H-bonding donors and H-Bonding acceptors

Chemistry 506 Dr. Hunter s Class Chapter 15. 8 15B Section(s) 18.2 Amino Acids having Amine/Heterocyclic Containing Side Chains Amino Acids (Building Blocks of Proteins) Generic AA = H 2 N-CHR-CO 2 H Lysine (basic) R = CH 2 CH 2 CH 2 CH 2 -NH 2 Tryptophan (neutral polar) Nitrogen is in aromatic bond H 2 C N H Histidine (basic) H 2 C N N H Arginine (basic) CH 2 CH 2 CH 2 NH-C(=NH 2 )-NH 2

Chemistry 506 Dr. Hunter s Class Chapter 15. 15C Section(s) 15.4 Amine Basicity 9 Simple Acid/Base Chemistry All Amines plus acids such as H + (ammonium salts) Neutralization of ammonium salts by bases such as OH -

Chemistry 506 Dr. Hunter s Class Chapter 15. 10 Amines plus Alkyl Halides Generic (Nucleophilic Attack and Deprotonation) NH 3 plus Alkyl Halides NH 2 R plus Alkyl Halides NHR 2 plus Alkyl Halides

Chemistry 506 Dr. Hunter s Class Chapter 15. 11 NR 3 plus Alkyl Halides no deprotonation possible

Chemistry 506 Dr. Hunter s Class Chapter 15. 12 15D Section(s) 15.5/6 Amides Generic Structures Properties Mp and Bp Polarization of Bonds Hydrogen Bonding Lone Pairs Neither Acidic or Basic

Chemistry 506 Dr. Hunter s Class Chapter 15. 13 IUPAC Nomenclature anamide examples Butanamide Benzamide N,N-dimethylbutanamide

Chemistry 506 Dr. Hunter s Class Chapter 15. 14 15E Section(s) 15.7/8 Amide Reactions Direct Synthesis from Carboxylic Acids and Amines Acid/Base reaction Thermolysis Synthesis from Acid Chlorides Synthesis from Anhydrides

Chemistry 506 Dr. Hunter s Class Chapter 15. 15 Nylon 66 Synthesis by Direct Reaction of Carboxylic Acids and Amines Synthesis from Acid Chlorides and Amines Related to Protein Backbones Polyamides with Side Chains

Chemistry 506 Dr. Hunter s Class Chapter 15. 16 Hydrolysis of Amides Acidic Hydrolysis (H 3 O + or H + /H 2 O) Basic Hydrolysis (OH - /H 2 O) Problems 15.1 to 15.41

Chemistry 506 Dr. Hunter s Class Chapter 15. 17 15F Section(s) 18.2 Amino Acids having Amide Containing Side Chains Amino Acids (Building Blocks of Proteins) Generic AA = H 2 N-CHR-CO 2 H Asparagine (neutral polar) R = CH 2 C(=O)-NH 2 Glutamine (neutral polar) R = CH 2 CH 2 C(=O)-NH 2

Chemistry 506 Dr. Hunter s Class Chapter 15. 18 Index of Topics and Vocabulary 1 1,3-C 4 H 4 N 2... 6 1... 2 2 2... 2 3 3... 3 4 4... 3 A Acid Chlorides... 15, 16 Acid/Base Chemistry... 10 Acidic... 13 Acidic Hydrolysis... 17 Alkyl Amines... 4 Alkyl Halides... 11 Amide Reactions... 15 Amides... 13 Amine Basicity... 10 Amine Classification... 2 Amines... 2, 15, 16 Amino Acids... 9, 18 Amino Acids having Amide Containing Side Chains... 18 Amino Acids having Amine/Heterocyclic Containing Side Chains... 9 Ammonia... 2 ammonium salts... 10 anamide... 14 Anhydrides... 15 Aniline... 5 Arginine... 9 aromatic... 9 Aromatic Amines... 5 Asparagine... 18 B Basic... 13 Basic Hydrolysis... 17 Benzamide... 14 Bp... 7, 13 Butanamide... 14 C C 4 H 5 N... 6 C 4 H 9 N... 6 C 5 H 11 N... 6 C 5 H 5 N... 6 Cadaverine... 7 Carboxylic Acids... 15, 16 coal tar... 5, 6 D Deprotonatio... 11 deprotonation... 12 Dimethyl Amine... 4 Direct Synthesis... 15 G Glutamine... 18 H H + /H 2 O... 17 H 3 O +... 17 H-Bonding acceptors... 7 H-bonding donors... 7 Heterocyclic Amines... 6 Histidine... 9 Hydrogen Bonding... 7, 13 Hydrogen Bonding Acceptor... 7 Hydrogen Bonding Donor... 7 Hydrolysis... 17 I IUPAC... 4, 14 L Lone Pairs... 13 Lysine... 9 M Methyl Ethyl Amine... 4 Mp... 7, 13 N N,N-dimethylbutanamide... 14 Neutralization... 10 NH 2 R... 11 NH 3... 11 NHR 2... 11 N-methyl-N-ethyl aniline... 5 Nomenclature... 4, 14 NR 3... 12 Nucleophilic Attack... 11 Nylon 66... 16 O OH -... 10 OH - /H 2 O... 17 P Piperidine... 6 Polar... 7 Polarization of Bonds... 13 Polyamides... 16 Primary Amine... 2

Chemistry 506 Dr. Hunter s Class Chapter 15. 19 Problems... 17 Properties... 7, 13 Protein Backbones... 16 Proteins... 9, 18 Putrescine... 7 Pyridine... 6 Pyrimidine... 6 Pyrole... 6 Pyrrolidine... 6 Q Quaternary Ammonium Salts... 3 S Secondary Amine... 2 Solubility... 7 Stench!... 7 T Tertiary Amine... 3 Tetramethyl Ammonium Chloride... 4 Thermolysis... 15 Tryptophan... 9

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