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Reagent/Substrate H H H H H 2-methylbutane 2-methyl-propene-1 Z-2-butene E-2-butene 1-propyne 2-butyne Br2(in the dark) No reaction meso Br2, hv Br2/H2O (in the dark) No reaction Br2/CH2OH In the dark) No reaction No reaction No reaction No reaction No reaction HBr No reaction H H CH, CH, H,C. CH, CH1CH2 Br CHyCH2 Br H. H2C CH, CH3 CH, And enantiomer Markovnikov Markovnikov Bromide ion attacks vinyl And enantiomer Achiral cation so Br and methyl groupareanti D2 Pd/C No reaction D2 Lindlar's catalyst No reaction No reaction No reaction No reaction CH, CH, H,C 'D D Syn addition Syn addition Li,ND, No reaction CH, D. CH, Dissolving metal reduction Anti addition Li NH2 No reaction (1) Li' NH2 (2) CH2 No reaction No reaction No reaction No reaction H3C CH3 No reaction (2) Zn No reaction KMnO4, H' No reaction Reagent / Substrate Br Br Br OH 2-bromo-2-methylbutane 2-methyl-butanol-2 bromobenzene bromoethene H2O Mg, Et2O 1. Mg 2. H2O SOCI2 No reaction No reaction HCI No reaction No reaction % And enantiomer Markovnikov PBr3 No reaction No reaction 1. Li 2. Cul (CH3CH2)2Culif 1.Li 2.D2O 2. Mg, Et2O 2.D2O

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