Question

1. Predict the products for each of the following reactions. Show stereochemistry of products. If enantiomers are formed, show both. HCI НВ НС HBr HI HС

Answer 1

All the given reactions undergo via protonation of alkene first to give the most stable carbocation first and then the halide ion attacks as a nucleophile to give a new C-X bond with 50-50% of each isomer.

CH3 HC HC Hoc 06 HC HACCI C CH (3S)-3-chloro-3-methyl (3R)-3-chloro-3-methyl hexane hexane H3C H2c CH3 2-bromo-2-methylpentane HCI CH3 H3C RY CH2 (2R)-2-chloro- 3,3-dimethylpe ntane CH3 H CSX CH3 CH3 CH3 (2S)-2-chloro-3,3 -dimethylpentane CH2 HB Y CH3 CH3

x H₃C H₂ H₃C (1R)-1-iodo-1,3,3-tri methylcyclopentane H₂C i (15)-1-iodo-1,3,3-tri methylcyclopentane HCI HCVRCH3 C C SYRCH, H3C SS CH3 (1R,3S)-1-chloro-3-ethyl ny (1 ,3S)-1-chloro-3-ethyl -1-methylcyclohexane -1-methylcyclohexane