Review of Alkene Reactions in Organic Chemistry: Stability and Addition Reactions - Prof. , Study notes of Organic Chemistry

Download Review of Alkene Reactions in Organic Chemistry: Stability and Addition Reactions - Prof. and more Study notes Organic Chemistry in PDF only on Docsity! CHEM 20481 - Basic Organic Chemistry - Chapter 6 Review Alkene Reactions Stability of Alkenes In general, more highly-substituted alkenes are more stable. tetrasubstituted > trisubstituted > disubstituted > monosubstituted Reactions of Alkenes C C H H H2 GGGGGGGA Pt, Pd, ... R(R’)CH-CH3 syn addition C C H H HX GGGGGGGA R(R’)CX-CH3 Follows Markovnikov’s Rule HI > HBr > HCl > > HF C C H H HBr GGGGGGGGA radical R(R’)CH-CH2X Anti-Markovnikov Addition C C H H H2O GGGGGGGGA H2SO4 R(R’)C(OH)-CH3 Markovnikov Addition C C H H 1) BH3/THF GGGGGGGGGGGGGGGGGGGGA 2) H2O2, OH−, H2O R(R’)CH-CH2OH Anti-Markovnikov Addition C C H H X2 GGGGGGA R(R’)CX-CH2X anti addition C C H H X2 GGGGGGA H2O R(R’)C(OH)-CH2X Markovnikov Addition C C H H peroxy acid GGGGGGGGGGGGGGGA (CH3COOOH) H H C C O (Formation of an epoxide) C C H H 1) O3 GGGGGGGGGGA 2) Zn, H2O RC(=O)R’ + H2C=O Products are ketone(s) and/or aldehyde(s) Mechanisms You should know (be able to draw) the mechanisms for the following reactions. See your textbook for details. • Addition of hydrogen halides (HX) • Carbocation rearrangements during addition reactions • Acid-catalyzed hydration of alkenes ( H2O GGGGGGGGA H2SO4 ) • Hydroboration ( BH3 GGGGGGGGA THF ) • Halogenation (X2) • Formation of halohydrins ( X2 GGGGGGA H2O )