Chemistry 121(01) Winter 2014 Introduction to Organic Chemistry and Biochemistry Instructor Dr. Upali Siriwardane (Ph.D. Ohio State) E-mail: upali@latech.edu Office: 311 Carson Taylor Hall ; Phone: 318-257-4941; Office Hours: MTW 9:00 am - 11:00 am; TR 9:00 - 10:00 am & 1:00-2:00 pm. December 20, Test 1 (Chapters 12-13) January 27 Test 2 (Chapters 14-16) February 14 Test 3 (Chapters 17-19) February 26, Test 4 (Chapters 20-22) February 27, 2014, Make Up Exam: Bring Scantron Sheet 882-E

Chapter 17: Amines and Amides 17.1 Bonding Characteristics of Nitrogen Atoms in Organic Compounds, 547 17.2 Structure and Classification of Amines, 548 17.3 Nomenclature for Amines, 549 17.4 Isomerism for Amines, 551 17.5 Physical Properties of Amines, 552 17.6 Basicity of Amines, 553 17.7 Reaction of Amines with Acids, 554 17.8 Alkylation of Ammonia and Amines, 557 17.9 Heterocyclic Amines, 558 17.10 Selected Biochemically Important Amines, 560 17.11 Alkaloids, 565 17.12 Structure and Classification of Amides, 568 17.13 Nomenclature for Amides, 570 17.14 Selected Amides and Their Uses, 571 17.15 Basicity of Amides, 572 17.16 Physical Properties of Amides, 573 17.17 Preparation of Amides, 574 17.18 Hydrolysis of Amides, 576 17.19 Polyamides and Polyurethanes, 578 CHEM 121 Winter 2013

Bonding Characteristics of Amines & Amides Hydrocarbons compounds containing nitrogen are the focus of the chapter 17 on amines and amides. Amines are carbon-hydrogen-nitrogen compounds, derived form ammonia Amides contain oxygen in addition to these elements. Amines and amides occur widely in living organisms. . CHEM 121 Winter 2014

Hydrogen bonding in Amines N-H- - - -N hydrogen bonds are weaker than O-H- - - -O CHEM 121 Winter 2013

Physical Properties of Amines CHEM 121 Winter 2013

Hydrogen bonding in Amides CHEM 121 Winter 2013

Odor or smell of Amines Most other amines are liquids and have odors resembling that of raw fish (strong, disagreeable odors). Foul smell from dead fish and decaying flesh is due to diamines released by the bacterial decomposition of protein. Examples: putrescine and cadaverine. CHEM 121 Winter 2013

Common Names of Amines CHEM 121 Winter 2013

IUPAC Nomenclature of Amines CHEM 121 Winter 2013

Common/IUPAC Nomenclature of Amides CHEM 121 Winter 2013

1. Identify the amines and amides from the following and give their common and/or IUPAC names. a)Type:_____________ Name:______________ b) Type:___________________ Name:__________________ c)Type:___________________ d)Type:____________ e) Type:___________________ f) Type:___________________ CHEM 121 Winter 2013

1. Identify the amines and amides from the following and give their common and/or IUPAC names. Type:___________________ Name:__________________ h) i) j) Type:___________________ Name:__________________ k) l) CHEM 121 Winter 2013

Cyclic Amines CHEM 121 Winter 2013

1. Identify the amines and amides from the following and give their common and/or IUPAC names. Type:___________________ Name:__________________ n) o) CHEM 121 Winter 2013

Basicity: Amine Salt formation Amines have a basic PH PH> 7 CHEM 121 Winter 2013

2. Classify each of the following as either 1', 2', or 3' amines and quaternary amine : CHEM 121 Winter 2013

3. Consider the following compounds: a) CH3—CH2—CH2—NH2 b) CH3—CH2—NH—CH3 c) CH3—CH2—CH2—CH3 d) CH3—CH2—CH2—NH3+Cl- Arrange compounds in the order highest boiling point to lowest?   B. Arrange compounds in the order of highest solubility in water to the lowest? CHEM 121 Winter 2013

4. Draw the structure of the following amines and amides: a) N-methyl-1-butanamine:   b) N-methylaniline c) N-phenyl-3-chlorobutanamide  d) N-ethyl-N-methylethanamide e) N-methylbenzamide CHEM 121 Winter 2013

Preparation of Amines Reaction of ammonia with alkyl halides b) Reduction of amides c) Reduction of Nitro Groups CHEM 121 Winter 2013

Preparation of Amines Reaction of ammonia with alkyl halides b) Reduction of amides c) Reduction of Nitro Groups CHEM 121 Winter 2013

Preparation of Amides Reaction with carboxylic acid to form amides (described below in preparation of amides) Polymerization to form polyamides Nylon 66 – a polymer of hexanedioic acid and 1,6-hexanediamine as monomers shown below CHEM 121 Winter 2013

Chemical Reactions of Amides Hydrolysis reaction amides (Acid/base hydrolysis) Reduction of amides to amines CHEM 121 Winter 2013

5) Name and complete the following preparations/reactions of amines and amides: b) c) d) CHEM 121 Winter 2013

5) Name and complete the following preparations/reactions of amines amides: CHEM 121 Winter 2013

5) Name and complete the following preparations/reactions of amines amides: j) k) CHEM 121 Winter 2013

5) Name and complete the following preparations/reactions of amines amides: CHEM 121 Winter 2013

Drugs & Narcotics CHEM 121 Winter 2013

Heterocyclic Amines and Alkaloids Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.[5] CHEM 121 Winter 2013

Heterocyclic Amines and Alkaloids CHEM 121 Winter 2013

Cocaines CHEM 121 Winter 2013

Chlorophyll and Hemoglobin CHEM 121 Winter 2013

Purines and Pyrimidines: DNA Bases CHEM 121 Winter 2013