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Organic Chemistry Lecture 20

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Chapter 20 ? 2010, Prentice Hall Organic Chemistry, 7th Edition L. G. Wade, Jr. Carboxylic Acids Chapter 20 * Introduction The functional group of carboxylic acids consists of a C?O with ?OH bonded to the same carbon. Carboxyl group is usually written ?COOH. Aliphatic acids have an alkyl group bonded to ?COOH. Aromatic acids have an aryl group. Fatty acids are long-chain aliphatic acids. Chapter 20 Chapter 20 * Common Names Many aliphatic acids have historical names. Positions of substituents on the chain are labeled with Greek letters starting at the carbon attached to the carboxylic carbon. Chapter 20 Chapter 20 * IUPAC Names Remove the final -e from alkane name, add the ending -oic acid. The carbon of the carboxyl group is #1. Chapter 20 Chapter 20 * Unsaturated Acids

Organic Chemistry Lecture 19b

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Chapter 8 ? 2010, Prentice Hall Organic Chemistry, 7th Edition L. G. Wade, Jr. Reactions of Alkenes Chapter 8 * Bonding in Alkenes Electrons in pi bond are loosely held. The double bond acts as a nucleophile attacking electrophilic species. Carbocations are intermediates in the reactions. These reactions are called electrophilic additions. Chapter 8 Chapter 8 * Electrophilic Addition Step 1: Pi electrons attack the electrophile. Step 2: Nucleophile attacks the carbocation. Chapter 8 Chapter 8 * Types of Additions Chapter 8 Chapter 8 * Addition of HX to Alkenes Step 1 is the protonation of the double bond. The protonation step forms the most stable carbocation possible. In step 2, the nucleophile attacks the carbocation, forming an alkyl halide.

Organic Chemistry Lecture 19a

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Chapter 19 ? 2010, Prentice Hall Organic Chemistry, 7th Edition L. G. Wade, Jr. Amines Chapter 19 * Biologically Active Amines The alkaloids are an important group of biologically active amines, mostly synthesized by plants to protect them from being eaten by insects and other animals. Many drugs of addiction are classified as alkaloids. Chapter 19 * Biological Activity of Amines Dopamine is a neurotransmitter. Epinephrine is a bioregulator. Niacin, Vitamin B6, is an amine. Alkaloids: nicotine, morphine, cocaine Amino acids Chapter 19 Chapter 19 * Classes of Amines Primary (1?): Has one alkyl group bonded to the nitrogen (RNH2). Secondary (2?): Has two alkyl groups bonded to the nitrogen (R2NH). Tertiary (3?): Has three alkyl groups bonded to the nitrogen (R3N).

Organic Chemistry Lecture 15

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Chapter 15 ? 2010, Prentice Hall Organic Chemistry, 7th Edition L. G. Wade, Jr. Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy Chaper 15 * Conjugated Systems Conjugated double bonds are separated by one single bond. Isolated double bonds are separated by two or more single bonds. Conjugated double bonds are more stable than isolated ones. Chaper 15 Chaper 15 * Heat of Hydrogenation of Conjugated Bonds For conjugated double bonds, the heat of hydrogenation is less than the sum for the individual double bonds. The more stable the compound, the less heat released during hydrogenation, Conjugated double bonds have extra stability. Chaper 15 Chaper 15 * Relative Stabilities twice 1-pentene more substituted Chaper 15 Chaper 15 * Structure of 1,3-Butadiene

Organic Chemistry Lecture 19

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Chapter 19 ? 2010, Prentice Hall Organic Chemistry, 7th Edition L. G. Wade, Jr. Amines Chapter 19 * Biologically Active Amines The alkaloids are an important group of biologically active amines, mostly synthesized by plants to protect them from being eaten by insects and other animals. Many drugs of addiction are classified as alkaloids. Chapter 19 Chapter 19 * Biological Activity of Amines Dopamine is a neurotransmitter. Epinephrine is a bioregulator. Niacin, Vitamin B6, is an amine. Alkaloids: nicotine, morphine, cocaine Amino acids Chapter 19 Chapter 19 * Classes of Amines Primary (1?): Has one alkyl group bonded to the nitrogen (RNH2). Secondary (2?): Has two alkyl groups bonded to the nitrogen (R2NH). Tertiary (3?): Has three alkyl groups bonded to the nitrogen (R3N).

Organic Chemistry Lecture 18

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Chapter 18 ?2010, Prentice Hall Organic Chemistry, 7th Edition L. G. Wade, Jr. Ketones and Aldehydes Chapter 18 * Carbonyl Compounds Chapter 18 Chapter 18 * Carbonyl Structure Carbon is sp2 hybridized. C?O bond is shorter, stronger, and more polar than C?C bond in alkenes. Chapter 18 Chapter 18 * Ketone Nomenclature Number the chain so that carbonyl carbon has the lowest number. Replace the alkane -e with -one. 3-methyl-2-butanone 4-hydroxy-3-methyl-2-butanone C H 3 C O C H C H 3 C H 3 C H 3 C O C H C H 3 C H 2 O H 1 2 3 4 1 2 3 4 Chapter 18 Chapter 18 * Ketone Nomenclature (Continued) For cyclic ketones, the carbonyl carbon is assigned the number 1. 3-bromocyclohexanone O B r 1 3 Chapter 18 Chapter 18 * C H 3 C H 2 C H C H 3 C H 2 C H O Aldehydes Nomenclature

Organic Chemistry Lecture 17

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Chapter 8 ? 2010, Prentice Hall Organic Chemistry, 7th Edition L. G. Wade, Jr. Reactions of Alkenes Chapter 8 * Bonding in Alkenes Electrons in pi bond are loosely held. The double bond acts as a nucleophile attacking electrophilic species. Carbocations are intermediates in the reactions. These reactions are called electrophilic additions. Chapter 8 Chapter 8 * Electrophilic Addition Step 1: Pi electrons attack the electrophile. Step 2: Nucleophile attacks the carbocation. Chapter 8 Chapter 8 * Types of Additions Chapter 8 Chapter 8 * Addition of HX to Alkenes Step 1 is the protonation of the double bond. The protonation step forms the most stable carbocation possible. In step 2, the nucleophile attacks the carbocation, forming an alkyl halide.

Organic Chemistry Lecture 15

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Chapter 15 ? 2010, Prentice Hall Organic Chemistry, 7th Edition L. G. Wade, Jr. Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy Chaper 15 * Conjugated Systems Conjugated double bonds are separated by one single bond. Isolated double bonds are separated by two or more single bonds. Conjugated double bonds are more stable than isolated ones. Chaper 15 Chaper 15 * Heat of Hydrogenation of Conjugated Bonds For conjugated double bonds, the heat of hydrogenation is less than the sum for the individual double bonds. The more stable the compound, the less heat released during hydrogenation, Conjugated double bonds have extra stability. Chaper 15 Chaper 15 * Relative Stabilities twice 1-pentene more substituted Chaper 15 Chaper 15 * Structure of 1,3-Butadiene

Organic Chemistry Lecture 14

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Chapter 14 ? 2010, Prentice Hall Organic Chemistry, 7th Edition L. G. Wade, Jr. Ethers, Epoxides, and Sulfides Chapter 14 * Ethers Formula is R?O?R???where R and R? are alkyl or aryl. Symmetrical or unsymmetrical O C H 3 C H 3 O C H 3 Chapter 14 Chapter 14 * Structure and Polarity Oxygen is sp3 hybridized. Bent molecular geometry. C?O?C angles is 110?. Polar C?O bonds. Dipole moment of 1.3 D. Chapter 14 Chapter 14 * Boiling Points Similar to alkanes of comparable molecular weight. Chapter 14 Chapter 14 * Hydrogen Bond Acceptor Ethers cannot hydrogen-bond with other ether molecules. Molecules that cannot hydrogen-bond intermolecularly have a lower boiling point. Ether molecules can hydrogen-bond with water and alcohol molecules. Chapter 14 Chapter 14 *

Organic Chemistry Lecture 11b

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Chapter 11 * Reaction with HBr ?OH of alcohol is protonated. ?OH2+ is good leaving group. 3? and 2? alcohols react with Br- via SN1. 1? alcohols react via SN2. H 3 O + B r - R O H R O H H R B r Chapter 11 Chapter 11 * Reaction with HCl Chloride is a weaker nucleophile than bromide. Add ZnCl2, which bonds strongly with ?OH, to promote the reaction. The chloride product is insoluble. Lucas test: ZnCl2 in concentrated HCl: 1? alcohols react slowly or not at all. 2? alcohols react in 1-5 minutes. 3? alcohols react in less than 1 minute. Chapter 11 Chapter 11 * SN2 Reaction with the Lucas Reagent Primary alcohols react with the Lucas reagent (HCl and ZnCl2) by the SN2 mechanism. Reaction is very slow. The reaction can take from several minutes to several days. Chapter 11 *

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