Orgo 2 reaction mechanisms Comprehensive Questions and Solutions Graded A+

Orgo 2 reaction mechanisms
Comprehensive Questions and
Solutions Graded A+
hydrohalogenation - Answer: add h-x

solvent= CH3COOH

mark

allows for rearangment

yeilds: breaks double bond and places halogen on most substituted carbon



Acid-Catalyzed Hydration - Answer: add H20

solvent: H2SO4

mark

allows rearangment

yeilds. breaks doublebond and places OH on more substituted carbon



Halogenation - Answer: add X2 (Cl, or Br)

spolvent (CH2Cl2)

NO regeoselectivity

anti-stereospecific

yeilds: breaks double bonds and places X on both sites

creates bridged halonuim ion PREVENTS rearangement

, Halohydrination - Answer: add X2+H2O (HOX)

solvent (H2O)

Mark

anti-stereospecific

yeilds: mark addition of OH and X

creates halonium bridge PREVENTS rearrangement



Oxymercuration/Reduction - Answer: part 1: add Hg(OAc)2 in H2O

part 2: NaBH4

solvent H2O

mark

anti-sterospecific

creates bridge PREVENTS rearrangement

yeilds: mark addition of OH



Hydroboration/Oxidation - Answer: 1: add BH3, THF

2: add H2O2, NaOH

solvent THF

Anti-mark

syn-stereospecific

yeilds anti mark addition of OH

usually to a termally alkene



Oxidation with Osmium tetroxide - Answer: 1. add OsO4

2. NaHSO3 and H2O

no regio specificity