Contents CHAPTER 10 Hydride Reduction of a Carbonyl Group 450 CHAPTER 11 Reaction of a Tertiary Alcohol with HBr(SN1)477 r Alcohol with HBr (S.2)477 Reaction ohols with PB 48 (Review):Acid-Catalyzed Dehydration of an Alcohol 484 The Pinacol Rearrangement 491 CHAPTER 14 Cleavage of an Ether by HBr or HI 639 Acid-Catalyzed Opening of Epoxides in Water 648 Acid-Catalyzed Opening of an Epoxide in an Alcohol Solution 649 Base-Catalyzed Opening of Epoxides 651 CHAPTER 15 1,2-and 1,4-Addition to a Conjugated Diene 673 Free-Radical Allylic Bromination 676 CHAPTER 17 Bro Nitmiontion of Benzengse nzene 757 Friedel Crafts Alkylation 774 Friedel-Crafts Acylation 778 (Benzyne M The Birch Reduction 788 CHAPTER 18 The Wittig Reaction 836 Hydration of Ketones and Aldehydes 839 Formation of Cyanohvdrins 840 Wolff-Kishner Reduction 857 ution of Pyridin e893 Acylation of an Amine by an Acid Chloride 895 Hofmann Elimination 899 The Cope Elimination of an Amine Oxide 903 Diazolization of an Amine 904 The Hofmann Rearrangement of Amides 921 CHAPTER 20 Nucleophilic Acyl Substitution in the Basic Hydrolysis of an Ester 959 Esterification Using Diazomethane 964 CHAPTER 21 Conversion of an Acid Chloride to an Anhydride 1000 Conversion of an Acid Chloride to an Ester 1000 n of an Acid Chloride an Am nide 1001 Conversion of an Acid Anhydride to an Este 100 Conversion of an Acid Anhydride to an Amid Convers 1007 ion of an Ester 1009 Basic Hydrolysis of an Amide 101 Acidic Hydrolysis of an Amide 1011 xx Contents CHAPTER 10 Hydride Reduction of a Carbonyl Group 450 CHAPTER 11 Reaction of a Tertiary Alcohol with HBr (SN1) 477 Reaction of a Primary Alcohol with HBr (SN2) 477 Reaction of Alcohols with PBr3 481 (Review): Acid-Catalyzed Dehydration of an Alcohol 484 The Pinacol Rearrangement 491 CHAPTER 14 Cleavage of an Ether by HBr or HI 639 Acid-Catalyzed Opening of Epoxides in Water 648 Acid-Catalyzed Opening of an Epoxide in an Alcohol Solution 649 Base-Catalyzed Opening of Epoxides 651 CHAPTER 15 1,2- and 1 ,4-Addition to a Conjugated Diene 673 Free-Radical Allylic Bromination 676 CHAPTER 17 Bromination of Benzene 753 Nitration of Benzene 756 Sulfonation of Benzene 757 Friedei-Crafts Alkylation 774 Friedei-Crafts Acylation 778 Nucleophilic Aromatic Substitution (Addition-Elimination) 783 Nucleophilic Aromatic Substitution (Benzyne Mechanism) 786 The Birch Reduction 788 CHAPTER 18 The Wittig Reaction 836 Hydration of Ketones and Aldehydes 839 Formation of Cyanohydrins 840 Wolff-Kishner Reduction 857 CHAPTER 19 Electrophilic Aromatic Substitution of Pyridine 892 Nucleophilic Aromatic Substitution of Pyridine 893 Acylation of an Amine by an Acid Chloride 895 Hofmann Elimination 899 The Cope Elimination of an Amine Oxide 903 Diazotization of an Amine 904 The Hofmann Rearrangement of Amides 921 CHAPTER 20 Nucleophilic Acyl Substitution in the Basic Hydrolysis of an Ester 959 Esterification Using Diazomethane 964 CHAPTER 21 Conversion of an Acid Chloride to an Anhydride 1000 Conversion of an Acid Chloride to an Ester 1000 Conversion of an Acid Chloride to an Amide 1001 Conversion of an Acid Anhydride to an Ester 1001 Conversion of an Acid Anhydride to an Amide 1002 Conversion of an Ester to an Amide (Ammonolysis of an Ester) 1002 Transesterification 1007 Saponification of an Ester 1009 Basic Hydrolysis of an Amide 1011 Acidic Hydrolysis of an Amide 1011