[PDF] [PDF] Chapter 15: Amines and Amides - Dr Allen D Hunter

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[PDF] Chapter 15: Amines and Amides - Dr Allen D Hunter

Section 6: Amines and Amides 6 5 AMIDE REACTIONS 2000-2002, Dr Allen D Hunter, Department of Chemistry, Youngstown State University 

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Chemistry 1506 Dr. Hunter's Class Section 6 Notes - Page 1/19

Chemistry 1506: Allied Health Chemistry 2

Secti on 6: Amines and Amides

Functional Groups with Single Bonds to Nitrogen

Outline

SECTION 6.1 AMINES........................................................................ SECTION 6.2 AMINO ACIDS HAVING AMINE/HETEROCYCLIC CONTAINING SIDE CHAINS.....8 SECTION 6.3 AMINE BASICITY........................................................................ SECTION 6.4 AMIDES........................................................................ 12 SECTION 6.5 AMIDE REACTIONS........................................................................ ........................................14 SECTION 6.6 AMINO ACIDS HAVING AMIDE CONTAINING SIDE CHAINS.....................................17

2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

Chemistry 1506 Dr. Hunter's Class Section 6 Notes - Page 2/19

Section 6.1 Amines

Amine Classification

Ammonia

1, Primary Amine

2Secondary Amine

2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

Chemistry 1506 Dr. Hunter's Class Section 6 Notes - Page 3/19

3, Tertiary Amine

4, Quaternary Ammonium Salts

2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

Chemistry 1506 Dr. Hunter's Class Section 6 Notes - Page 4/19

IUPAC Nomenclature

Named as Alkyl Amines (multiple words)

Dimethyl Amine

Methyl Ethyl Amine

Tetramethyl Ammonium Chloride

2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

Chemistry 1506 Dr. Hunter's Class Section 6 Notes - Page 5/19

Aromatic Amines

Aniline (coal tar)

N-methyl-N-ethyl aniline

2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

Chemistry 1506 Dr. Hunter's Class Section 6 Notes - Page 6/19

Heterocyclic Amines

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)

2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

Chemistry 1506 Dr. Hunter's Class Section 6 Notes - Page 7/19

Properties

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

2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

Chemistry 1506 Dr. Hunter's Class Section 6 Notes - Page 8/19 Section 6.2 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

N H 2 C H

Histidine (basic)

N N H 2 C H

Arginine (basic)

CH 2 CH 2 CH 2

NH-C(=NH

2 )-NH 2

2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

Chemistry 1506 Dr. Hunter's Class Section 6 Notes - Page 9/19

Section 6.3 Amine Basicity

Simple Acid/Base Chemistry

All Amines plus acids such as H

(ammonium salts)

Neutralization of ammonium salts by bases such

as OH

2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

Chemistry 1506 Dr. Hunter's Class Section 6 Notes - Page 10/19

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

2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

Chemistry 1506 Dr. Hunter's Class Section 6 Notes - Page 11/19 NR 3 plus Alkyl Halides no deprotonation possible

2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

Chemistry 1506 Dr. Hunter's Class Section 6 Notes - Page 12/19

Section 6.4 Amides

Generic Structures

Properties

Mp and Bp

Polarization of Bonds

Hydrogen Bonding

Lone Pairs

Neither Acidic or Basic

2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

Chemistry 1506 Dr. Hunter's Class Section 6 Notes - Page 13/19

IUPAC Nomenclature

anamide examples

Butanamide

Benzamide

N,N-dimethylbutanamide

2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

Chemistry 1506 Dr. Hunter's Class Section 6 Notes - Page 14/19

Section 6.5 Amide Reactions

Direct Synthesis from Carboxylic Acids and Amines

Acid/Base reaction

Thermolysis

Synthesis from Acid Chlorides

Synthesis from Anhydrides

2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

Chemistry 1506 Dr. Hunter's Class Section 6 Notes - Page 15/19

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

2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

Chemistry 1506 Dr. Hunter's Class Section 6 Notes - Page 16/19

Hydrolysis of Amides

Acidic Hydrolysis (H

3 O or H /H 2 O)

Basic Hydrolysis (OH

/H 2 O)

2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

Chemistry 1506 Dr. Hunter's Class Section 6 Notes - Page 17/19 Section 6.6 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

2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

Chemistry 1506 Dr. Hunter's Class Section 6 Notes - Page 18/19

Index of Topics and Vocabulary

1,3-C 4 H 4 N 2 ................................6 Basic........................................12

Basic Hydrolysis......................16

Bp........................................7, 12

C 4 H 5

Acid Chlorides..................14, 15

C 4 H 9

Acid/Base Chemistry................9

C 5 H 11 C 5 H 5

Acidic Hydrolysis....................16

Alkyl Amines............................4

Carboxylic Acids...............14, 15

Alkyl Halides..........................10

coal tar...................................5, 6

Amide Reactions.....................14

Amine Basicity..........................9

Dimethyl Amine........................4

Amine Classification.................2

Direct Synthesis.......................14

Amines..........................2, 14, 15

Amino Acids.......................8, 17

H /H 2

O....................................16

Amino Acids having Amide

Containing Side Chains........17

H 3 O

H-Bonding acceptors.................7

Amino Acids having

Amine/Heterocyclic

Containing Side Chains..........8

H-bonding donors......................7

Heterocyclic Amines.................6

Hydrogen Bonding..............7, 12

ammonium salts........................9

Hydrogen Bonding Acceptor.....7

Hydrogen Bonding Donor.........7

IUPAC.................................4, 13

Lone Pairs................................12

Aromatic Amines......................5

Methyl Ethyl Amine..................4

2000-2002, Dr. Allen D. Hunter, Department of Chemistry, Youngstown State University

Chemistry 1506 Dr. Hunter's Class Section 6 Notes - Page 19/19

Mp.......................................7, 12

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