IMPROVED Chapter 11 Mechanisms Study Guide (Organic Chemistry 1)

(H30+) or (H20, H2SO4)

Adding Water (Making Alcohols) [Hint: Acid-Catalyzed Hydration]

Hg(OAc)2, H2O, NaBH4

Adding Water (Making Alcohols) [Hint: Oxymercuration-Demercuration]

(1) BH3, THF (2) H2O2, NaOH

Adding Water (Making Alcohols) [Hint: Hydroboration-Oxidation]

HBr or HCl

Adding Halogens (Like Br or Cl) [Hint: Hydrohalogenation]

HBr/ROOR (peroxide)

Adding Halogens (Like Br or Cl) [Hint: Anti-Markovnikov Hydrohalogenation]

Br2 or Cl2

Adding Halogens (Like Br or Cl) [Hint: Halogenation]

Br2, H2O

Adding Halogens (Like Br or Cl) [Hint: Halohydrin Formation]

KMnO4, NaOH, cold

Adding Two −OH Groups (Dihydroxylation) [Hint: Syn-Addition]

RCO3H H3O+ OR MCPBA H3O+

Adding Two −OH Groups (Dihydroxylation) [Hint: Anti-Addition]

O3 & DMS or Zn/H2O

The Scissors (Ozonolysis) Pulls the two halves apart, and places a carbonyl oxygen hat (=O) on both of the newly cut ends

(H30+) or (H20, H2SO4)

Acid-Catalyzed Hydration

Hg(OAc)2, H2O, NaBH4

Oxymercuration-Demercuration

(1) BH3, THF (2) H2O2, NaOH

Syn-addition (the added −H and −OH both point in the same direction—both wedges or both dashes)

(1) BH3, THF (2) H2O2, NaOH

Hydroboration-Oxidation

HBr or HCl

Hydrohalogenation

HBr/ROOR (peroxide)

Hydrohalogenation with Peroxides (or Anti-Markovnikov Hydrohalogenation)

Br2 or Cl2

Anti-addition (they point in opposite directions—one wedge, one dash) [Hint: Halogenation]

Br2 or Cl2

Halogenation

Br2, H2O

Anti-addition (the −OH and −Br point in opposite directions—one wedge, one dash) [Hint: Halohydrin]

Br2, H2O

Halohydrin Formation

KMnO4, NaOH, cold

Pointing the Same Way (Syn-Addition)

KMnO4, NaOH, cold

Syn-Dihydroxylation

RCO3H H3O+ OR MCPBA H3O+

Anti-Dihydroxylation

O3 & DMS or Zn/H2O

Ozonolysis

(H30+) or (H20, H2SO4)

Puts −OH on the most crowded carbon (Markovnikov) [Hint: Acid-Catalyzed]

Hg(OAc)2, H2O, NaBH4

Puts −OH on the most crowded carbon (Markovnikov) [Hint: Oxymercuration]

(1) BH3, THF (2) H2O2, NaOH

Puts −OH on the least crowded (roomy) carbon (Anti-Markovnikov)

HBr or HCl

Puts the halogen on the most crowded carbon (Markovnikov)

HBr/ROOR (peroxide)

Puts the halogen on the least crowded carbon (Anti-Markovnikov)

Br2 or Cl2

Puts a halogen on both carbons of the old double bond

Br2, H2O

Adds one −Br and one −OH across the double bond

KMnO4, NaOH, cold

Stamps two −OH groups onto the same side of the molecule (both wedges or both dashes)

RCO3H H3O+ OR MCPBA H3O+

Puts two −OH groups pointing in opposite directions (one wedge, one dash)

Br2, H2O

-OH claims the most crowded carbon (Anti-Markovnikov)

Br2, H2O

Puts the halogen on the least crowded carbon (Anti-Markovnikov)