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Substitution reactions

Organic Chemistry Lecture 19b

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Chemistry
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Chemistry
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Functional groups
Name reactions
Substitution reactions
Amine
Amide
Amination
Imine
Nitrile
Sulfonamide
Aniline

Chapter 19 * Alkylation of Amines by Alkyl Halides Even if just one equivalent of the halide is added, some amine molecules will react once, some will react twice, and some will react three times (to give the tetraalkylammonium salt). Chapter 19 * Examples of Useful Alkylations Exhaustive alkylation to form the tetraalkylammonium salt. Reaction with large excess of NH3 to form the primary amine. C H 3 C H 2 C H C H 2 C H 2 C H 3 N ( C H 3 ) 3 C H 3 C H 2 C H C H 2 C H 2 C H 3 N H 2 3 C H 3 I N a H C O 3 + _ I C H 3 C H 2 C H 2 B r N H 3 ( x s ) C H 3 C H 2 C H 2 N H 2 + N H 4 B r Chapter 19 Chapter 19 * Acylation of Amines Primary and secondary amines react with acid halides to form amides. This reaction is a nucleophilic acyl substitution. Chapter 19 *

Organic Chemistry Lecture 19b

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Chemistry
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Chemistry
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Functional groups
Substitution reactions
Markovnikov's rule
Nucleophilic substitution
Alkene
Electrophile
Haloalkane
Amine
Nucleophilic acyl substitution
Amide
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 17

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Chemistry
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Chemistry
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Functional groups
Substitution reactions
Physical organic chemistry
Organic reactions
Name reactions
Markovnikov's rule
Alkene
Electrophile
Electrophilic aromatic substitution
Electrophilic addition
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 11b

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Chemistry
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Functional groups
Substitution reactions
Name reactions
Chlorides
Rearrangement reactions
Alcohol
SN1 reaction
Ester
Lucas' reagent
Pinacol rearrangement

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 *

Organic Chemistry Lecture 6

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Chemistry
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Substitution reactions
Nucleophilic substitution
Elimination reaction
SN1 reaction
SN2 reaction
Haloalkane
Leaving group
Aryl halide
Chemical reaction
Solvent effects

Chapter 6 Organic Chemistry, 7th Edition L. G. Wade, Jr. Alkyl Halides: Nucleophilic Substitution and Elimination ?2010, Prentice Hall Chapter 6 * Classes of Halides Alkyl halides: Halogen, X, is directly bonded to sp3 carbon. Vinyl halides: X is bonded to sp2 carbon of alkene. Aryl halides: X is bonded to sp2 carbon on benzene ring. C C H H H C l vinyl halide C H H H C H H B r alkyl halide I aryl halide Chapter 6 Chapter 6 * Polarity and Reactivity Halogens are more electronegative than C. Carbon?halogen bond is polar, so carbon has partial positive charge. Carbon can be attacked by a nucleophile. Halogen can leave with the electron pair. Chapter 6 Chapter 6 * IUPAC Nomenclature Name as haloalkane.
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