Lecture Presentation Chapter 18 Amines and Amides Karen C Timberlake General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Chapter 18 Amines and Amides Environmental health practitioners (EHPs) monitor environmental pollution to protect the health of the public By using specialized equipment, EHPs measure • • pollution levels in soil, air, and water noise and radiation levels General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Chapter 18 Readiness Core Chemistry Skills • Writing Equations for Reactions of Acids and Bases (10.6) • Naming and Drawing Alkanes (11.2) General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc 18.1 Amines Indigo used in blue dyes can be obtained from tropical plants such as Indigofera tinctoria Learning Goal Name amines using IUPAC and common names; draw the condensed or line-angle structural formulas when given the names Classify amines as primary (1°), secondary (2°), or tertiary (3°) General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Amines Amines • are derivatives of ammonia, NH3, in which one or more hydrogen atoms are replaced with alkyl or aromatic groups • contain N attached to one or more alkyl or aromatic groups CH3 —CH2—CH2 —N—CH3 CH3 H N H H—N—CH2—CH3 CH3 General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Naming Amines, IUPAC In the IUPAC names for amines, the e in the corresponding alkane name is replaced with amine Amines with a chain of three or more carbon atoms are numbered to show the position of the —NH group and any other substituents General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Naming Amines, IUPAC • If there is an alkyl group attached to the nitrogen atom, the prefix N and the alkyl name are placed in front of the amine name • If there are two alkyl groups bonded to the N atom, the prefix N is used for each, and they are listed alphabetically General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Guide to IUPAC Naming of Amines General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Study Check Give the IUPAC name for the following amine: General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Solution Give the IUPAC name for the following amine: STEP Name the longest carbon chain bonded to the N atom by replacing the e of its alkane name with amine General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc H-Bonding in 1° Amides Primary (1°) amides, can form • hydrogen bonds with the –NH2 group of other amides • hydrogen bonds with water molecules making them soluble in water as long as they have less than five carbons General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc H-Bonding in 2° Amides Secondary (2°) amides • • have lower melting points because they form fewer hydrogen bonds with other amides form hydrogen bonds with water molecules, making them soluble in water as long as they have fewer than five carbons General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc H-Bonding in 3° Amides Tertiary (3°) amides • have the lowest melting points because they form the fewest hydrogen bonds • can only form one hydrogen bond with H 2O General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Chemistry Link to Health: Amides and Medicine Urea is • • • the simplest natural amide the end product of protein metabolism in the body excreted in the urine If the kidneys malfunction, urea is not removed and builds to a toxic level, a condition called uremia General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Chemistry Link to Health: Amides and Medicine Aspirin substitutes • • contain phenacetin and acetaminophen act to reduce fever and pain but have little anti-inflammatory effect General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Chemistry Link to Health: Amides and Medicine Many barbituates • • are cyclic amides of barbituric acid act as sedatives in small doses or sleep inducers in large doses • are habit forming Barbiturate drugs include phenobarbital (Luminal) and pentobarbital (Nembutal) General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc 18.6 Hydrolysis of Amides In a reverse reaction of amidation, hydrolysis occurs when water and an acid or a base split an amide Learning Goal Write balanced chemical equations for the hydrolysis of amides General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Acid Hydrolysis of Amides Amides undergo acid hydrolysis with heat to produce a carboxylic acid and an ammonium salt Core Chemistry Skill Hydrolyzing Amides General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Base Hydrolysis of Amides Amides undergo base hydrolysis with heat to produce a carboxylate salt and an amine or ammonia General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Base Hydrolysis of Amides Draw the condensed structural formulas and give the IUPAC names for the products from the hydrolysis of N-methylpentanamide with NaOH ANALYZE Given Need THE hydrolysis of PROBLEM N-methylpentanamide structural formulas, with NaOH General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake products, condensed IUPAC names © 2016 Pearson Education, Inc Base Hydrolysis of Amides Draw the condensed structural formulas for the products from the hydrolysis of Nmethylpentanamide with NaOH In the base hydrolysis of the amide, • • the amide bond is broken between the carboxyl carbon atom and the nitrogen atom the products are the carboxylate salt and an amine General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Study Check Draw the condensed structural formula for the hydrolysis of the following amide with HCl: O heat CH3—CH2—C—N—CH3 General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake + H2O + HCl © 2016 Pearson Education, Inc Solution Draw the condensed structural formula for the hydrolysis of the following amide with HCl: O heat CH3—CH2—C—N—CH3 + H2O + HCl H + CH3—CH2—C—OH + H—N—CH3 O H General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Concept Map General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc ... nitrogen atom General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc General, Organic, and Biological Chemistry: Structures of Life,... General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Solubility of Amines in H2O General, Organic, and Biological Chemistry: Structures. .. Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Guide to IUPAC Naming of Amines General, Organic, and Biological Chemistry: Structures