Substitution reactions

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 *

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.

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.