西北农林科技大学：《有机化学 Organic chemistry》课程PPT教学课件（2014）Chapter 05 The Study of Chemical Reactions

有机化学oRCANIC CHEmISTRY 盖饼：王饺儒8709289l 理学院孟化素理科楼2层206 Organic Chemistry,6th Edition L.G.Wade,Jr Chapter 5 The Study of Chemical Reactions Key Notes Mechanism Homolytic cleavage;Heterolytic cleavage;Intermediate;Transition state Homework: 5-235-255-26(b,de)P182

Chapter 5 The Study of Chemical Reactions Key Notes Mechanism; Homolytic cleavage; Heterolytic cleavage; Intermediate; Transition state Organic Chemistry, 6th Edition L. G. Wade, Jr. 有机化学ORGANIC CHEMISTRY 主讲：王俊儒 87092829(o) 理学院应化系理科楼2层C206 Homework: 5-23; 5-25; 5-26（b,d,e）;(P182)

自秋不特大对 Content ■Introduction Classification of reactions Mechanisms:step-by-step pathway oIntermediate?Transition state? .Thermodynamics ●Kinetics

Content ◼Introduction ◼Classification of reactions ◼Mechanisms：step-by-step pathway ⚫Intermediate? Transition state? ⚫Thermodynamics ⚫ Kinetics

自秋转试对 Introduction 视中就 ■Reactants→Products:overall reaction. Mechanism:step-by-step pathway. To learn more about a reaction: ●Thermodynamics ●Kinetics

Introduction ◼Reactants → Products: overall reaction. ◼Mechanism: step-by-step pathway. ◼To learn more about a reaction: ⚫Thermodynamics ⚫Kinetics

0标4花对 Reactions Bond formation Synthetic organic chemistry is about creating complex molecules from simple starting materials a process which may involve many different reactions. Designing a synthesis is a bit like chess. a synthetic 'game strategy

Reactions Bond formation ◼ Synthetic organic chemistry is about creating complex molecules from simple starting materials - a process which may involve many different reactions. ◼ Designing a synthesis is a bit like chess. ◼ a synthetic 'game strategy

自精对 Reactions Bond formation Basically,most reactions involve electron- rich molecules forming bonds to electron deficient molecules (i.e.nucleophiles forming bonds to electrophiles). The bond will be formed specifically between the nucleophilic center of the nucleophile and the electrophilic center of the electrophile

Reactions Bond formation ◼ Basically, most reactions involve electron￾rich molecules forming bonds to electron deficient molecules (i.e. nucleophiles forming bonds to electrophiles). ◼ The bond will be formed specifically between the nucleophilic center of the nucleophile and the electrophilic center of the electrophile

音秋标特大对 Sec 1 Classification Reactions can be classified as ■Acid/base reactions Functional group transformations; oone functional group can be converted into another. Normally these reactions are relatively straightforward and proceed in high yield carbon-carbon bond formations

Sec 1 Classification Reactions can be classified as ◼Acid/base reactions ◼Functional group transformations; ⚫one functional group can be converted into another. ⚫Normally these reactions are relatively straightforward and proceed in high yield ◼carbon-carbon bond formations

Reaction category/Functional groups Electrophilic addition Alkenes and alkynes Electrophilic Aromatic substitution Nucleophlic addition Aldehydes and ketones Nucleophilic Carboxylic acid derivatives,Alkyl substitution halides Elimination Alcohols and alkyl halides Reduction Alkenes,alkynes,aromatic,aldehydes, ketones,nitriles,carboxylic acids, and carboxylic acid derivatives, Oxidation Alkenes,alcohols,aldehydes Acid/base reactions Carboxylic acids,phenols,amines

Electrophilic addition Alkenes and alkynes Electrophilic substitution Aromatic Nucleophlic addition Aldehydes and ketones Nucleophilic substitution Carboxylic acid derivatives, Alkyl halides Elimination Alcohols and alkyl halides Reduction Alkenes,alkynes, aromatic, aldehydes, ketones, nitriles, carboxylic acids, and carboxylic acid derivatives, Oxidation Alkenes, alcohols, aldehydes Acid/base reactions Carboxylic acids, phenols, amines Reaction category/ Functional groups

Examples ■Alkenes C=C ■Alkynes C三C ■Aromatic C6H6 0 0: Aldehydes and ketones C=0 ■Alkyl halides RX

Examples ◼Alkenes C=C ◼Alkynes C三C ◼Aromatic C6H6 ◼Aldehydes and ketones C=O ◼Alkyl halides RX

自秋转材对 Addition 视中院 X-Y Elimination + :Br :Br: :Br: Br: C-C An alkene +:Br: A bromonium ion 6- Br Alkene Productlike transition state Carbocation

Polarization 6+八8- 1. CH3 CH=CH2 SpB Sp2 6+ 6- 6+ 6- 2.C=C H X 3. δ+ +Br Br

Polarization 1. CH3——— CH=CH2 SP3 SP2 2. C=C + H——— X 3. C ＋ Br———Br C + - + - + - + -