Modern chlorination reagent for solution phase chlorination SOCl 2 Reagent that adds Br allylically to alkenes NBS What reagent causes anti- Markovnikoff addition during reactions of HX across alkenes ? H 2 O 2 (peroxides) Both solvent and base used in chlorination reagent for solution phase chlorination pyridine Reactions to RX round robin

Br 2 + >C=C< Solvent ??? CCl 4 (carbon tetrachloride) Modern, gas phase bromination reagent bubbled neat into ROH to brominate PBr 3 Inorganic acid used with NaBr and reflux to carry out `classic’ bromination of alcohols H 2 SO 4 H 2 O/CCl 4 Br 2 + (CH 3 ) 2 C=CH  ?? HO(CH 3 ) 2 C-CH 2 Br (OH adds markovnikoff)

Reactions to form RX from ROH are what class of reaction ? Substitutions Reactions of alkenes with HX or X 2 are what class of reaction ? Additions In the classical substitution of Br for OH in ROH, what is typically done to drive this rather inefficient reaction forward ? Reflux NBS/light/CCl 4 H 2 C=CH-CH  ????? H 2 C=CH-CH 2 Br

H 2 SO 4 HBr+ (CH 3 ) 2 C=CH  ?? Br(CH 3 ) 2 C-CH 3 H 2 SO 4 HBr+ (CH 3 ) 2 C=CH  ??? H 2 O 2 H(CH 3 ) 2 C-CH 2 Br CCl 4 Br 2 + (CH 3 ) 2 C=CH  ??? 25 o Br(CH 3 ) 2 C-CH 2 Br PBr 3 (g) bubbled neat C 4 H 9 OH  ?????? C 4 H 9 Br

Stop it, Doc !