有机化学Chapter 4. Alkynes 炔烃.pptVIP

Chapter 4 Alkynes 4.1 Nomenclature 4.2 Structure of Alkynes 4.3 Reactions of alkynes 4.3.1 Acidity of Terminal Alkynes （端位炔烃的酸性） 4.3.2 Application of the Acidity of Terminal Alkynes in Organic Synthesis （端位炔烃酸性在合成上的应用） 4.3.3 Hydrogenation of Alkynes 1. Syn-addition of H2: Synthesis of cis-Alkyenes 2. Metal-Ammonia Reduction of Alkynes Synthesis of trans-Alkenes 4.3.4 Electrophilic Addition of Alkynes a. Addition of HX b. Hydration of Alkynes c. Addition of X2 d. Hydroboration and Oxidation of Alkynes 4.4 Oxidation of Alkynes 4.5 Preparation of Unsaturated Hydrocarbons 4.5.1 Preparation of alkenes Dehydrohalogenation of alkyl halides 2. Dehydration (脱水)of alcohols 4.5.1 Preparation of Alkynes Dehydrohalogenation of vicinal alkyl dihalides b. Alkylation of alkynide ions Suffix: ane yne Alkynes: Hydrocarbons containing a carbon-carbon triple bond. 4.1 Nomenclature P128,4.13 1-Butyne Alkenyne (烯炔) 3-Penten-1-yne (3-戊烯-1-炔) 1-penten-4-yne (1-戊烯-4-炔) 1. Numbering starts from the end near the first multiple bond. 2. When there is a choice, double bonds receive lower numbers than triple bonds. 4， 8-壬二烯-1-炔 4.2 Structure of Alkynes Acetylene (ethyne): sp Hybrid orbitals C: Ground state 2p 2s 1s Promotion of electron Excited state 2p 2s 1s sp-hybridized state 1s 2p sp Hybri- dization Each sp hybrid orbital: 50% s character 50% p character P19, 1.9 The shape of an sp hybrid obital: The two sp hybride orbitals are oriented 180°away from each other, perpendicular to the two remaining p orbitals. 180° An sp-hybridized carbon atom: Geometric structure of sp-hybridized C atoms is linear. H H σbond πbond πbond Carbon-carbon triple bonds 4.3 Physical properties of alkynes 4.4 Reactions of alkynes 4.4.1 Acidity of Terminal Alkynes(p131) Acetylene: Carbanion Conjugate base (共轭碱) pKa: 25 44 50 Acidity: pKa: 3.2 15.8 16-17