1. 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

2. 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 2 -------------  ?? HO(CH 3 ) 2 C-CH 2 Br (OH adds markovnikoff)

3. 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 3 ---------------------  ????? H 2 C=CH-CH 2 Br

4. H 2 SO 4 HBr+ (CH 3 ) 2 C=CH 2 -------------  ?? Br(CH 3 ) 2 C-CH 3 H 2 SO 4 HBr+ (CH 3 ) 2 C=CH 2 -------------  ??? H 2 O 2 H(CH 3 ) 2 C-CH 2 Br CCl 4 Br 2 + (CH 3 ) 2 C=CH 2 -------------  ??? 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

5. Stop it, Doc !