西北农林科技大学：《有机化学 Organic chemistry》课程PPT教学课件（2013）Chapter 05 The Study of Chemical Reactions

自秋标转材 Organic Chemistry,6th Edition L.G.Wade,Jr. Chapter 5 The Study of Chemical Reactions Key Notes Mechanismj Homolytic cleavage;Heterolytic cleavage;Intermediate;Transition state By Junru Wang Email:wangjr07@163.com

By Junru Wang Email: wangjr07@163.com Chapter 5 The Study of Chemical Reactions Organic Chemistry, 6th Edition L. G. Wade, Jr. Key Notes Mechanism; Homolytic cleavage; Heterolytic cleavage; Intermediate; Transition state

自秋不转大对 Content 花单院 ■Introduction Classification of reactions Mechanisms:step-by-step pathway ●Intermediate？Transition state? ●Thermodynamics ●Kinetics

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

自秋特大材 Introduction ■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

自精对 Reactions 视中就 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

0标4化对 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

自秋东特试对 Sec 1 Classification Reactions can be classified as ■Acid/base reactions Functional group transformations; oone functional group can be converted into another. oNormally 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 CsH6 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

自秋转大材 Addition 花单院 -Y Elimination :Br: :Br: :Br Br: C三( An alkene :Br: A bromonium ion 8-t Br Alkene Productlike transition state Carbocation

axi女 1.5 bonds on average H 2007 Thomson Higher Education Naphthalene