Organic Chem CH 8 Reactions

H and X

What is added in a hydrohalogenation?

Hydrohalogenation

What reaction may use the following reagents? Reagents: H and X

Markovnikov

What type of regiochemistry does a hydrohalogenation reaction have?

rearrangement is possible

What is special about a carbocation in a hydrohalogenation reaction?

H and OH

What is added in an acid-catalyzed reaction?

Acid-Catalyzed Hydration

The following reagents would be seen in what type of reaction? Reagents: H3O+, H2SO4 and H2O, H+ and H2O.

Markovnikov

What type of regiochemistry is observed in acid catalyzed hydration reactions?

rearrangement is possible

What is special about carbocations in an acid catalyzed hydration reaction?

H and OH

What is added in an oxymercuration-demercuration reaction?

Oxymercuration-Demercuration Hydration

What reaction may use the following reagents? Reagents: Hg(OAc)2 and H2O or NaBH4

Markovnikov

What type of regiochemistry does an oxymercuration-demercuration reaction have?

Anti addition

What type of stereochemistry does an oxymercuration-demercuration hydration reaction have?

no rearrangement is possible

What is special about a carbocation in an oxymercuration-demercuration hydration reaction?

H and OH

What is added in a hydroboration-oxidation reaction?

Hydroboration-Oxidation Hydration

Which reaction may use the following reagents? Reagents: BH3 and THF or H2O2 and OH-

Non-markovnikov (H opposite)

What type of regiochemistry does a hydroboration-oxidation hydration reaction have?

Syn addition

What type of stereochemistry is shown in a hydroboration-oxidation hydration reaction?

no rearrangement is possible

What is special about carbocations in a hydroboration-oxidation reaction?

H and H

What is added in a Catalytic Hydrogenation reaction?

Catalytic Hydrogenation

Which reaction may use the following reagents? Reagents: H2 and Pt, Pd, or Ni

no regiochemistry

What type of regiochemistry does a catalytic hydrogenation reaction have?

Syn Addition

What type of stereochemistry does a catalytic hydrogenation reaction have?

no rearrangement is possible

What is special about carbocations in a catalytic hydrogenation reaction?

X and X

What is added in a Halogenation reaction?

Halogenation

What reaction may use the following reagents? Reagents: Cl2 or Br2 in solvent

no regiochemistry

What regiochemistry does a halogenation reaction have?

Anti Addition

What type of stereochemistry does a halogenation reaction have?

no rearrangement is possible

What is special about carbocations in a halogenation reaction?

X and OH

What is added in a halohydrin formation reaction?

Halohydrin formation reaction

What reaction may use the following reagents? Reagents: X2 and H2O

Similar to Markovnikov, X acts like H

What type of regiochemistry does a halohydrin formation reaction have?

Anti Addition

What type of stereochemistry does a halohydrin formation reaction have?

no rearrangement is possible

What is special about carbocations in a halohydrin formation reaction?

OH and OH (a diol)

What is added in a Hydroxylation reaction?

Anti Hydroxylation

What reaction may use the following reagents? Reagents: RCO3H, H3O+, MCPBA

Syn Hydroxylation

What reaction may use the following reagents? Reagents: KMnO4 and NaOH, or OsO4 and H2

Anti addition

What type of stereochemistry does an anti-hydroxylation reaction have?

Syn addition

What type of stereochemistry does a syn hydroxylation reaction have?

no rearrangement is possible

What is special about carbocations in both anti and syn hydroxylation reactions?

Weak oxidative cleavage of double bond

What occurs in an oxidation-ozonolysis reaction?

Oxidation-ozonolysis

What reaction may use the following reagents? Reagents: O3 or a reducing agent such as DMS or Zn/H2O