1559r.ch12.220-24611/02/0521:55Page223 EQA 88音导8 66格说销 ⊕ 223223 CHART OF EXAMPLES Electrophilic Additions to 1-Methylcyclohexene Typical Regiochemistry Major Example reagent Electrophile Nucleophile Intermediate Stereochemistry Product Hydroboration BH3 B H None anti-Markovnikov syn addition HX addition HCl H Cl Markovnikov Hydration H2SO4, H2O H H2O Markovnikov Halogenation ICl I Cl Haloalcohol Cl2, H2O Cl H2O formation Chlorosulfenylation CH3SCl CH3S Cl Oxymercuration Hg(OCCH3)2, H2O CH3COHg H2O OH CH3 H O HgOCCH3 CH3 O HgOCCH3  Cl CH3 SCH3 H CH3 SCH3  OH CH3 Cl H CH3 Cl Cl CH3 I H CH3 I CH3 OH CH3  CH3 Cl CH3  CH3 H H B(H, R)2 O B O B Markovnikov anti addition Markovnikov anti addition Markovnikov anti addition Markovnikov anti addition 1559T_ch12_220-246 11/02/05 21:55 Page 223