Chem 331 - Exam 3 Addition Reactions

What reaction is this?

Syn Dihydroxylation

• Does SYN addition

• Uses OsO4, Na2SO3 or NaHSO3, and H2O

What reaction is this?

Anti Dihydroxylation

• Does ANTI addition

• Uses RCO3H (mCBPA) and H3O+

What reaction is this?

Halohydrin

• Uses halogens (Br2) and H2O

• Does ANTI addition

• Add OH group to HIGHER substituted carbon

What reaction is this?

Hydrohalogenation

• Uses H-X (X = halide)

• Favors Markovnikov product (unless ROOR/H2O2 present)

• Product has chiral center = forms racemic mix of R and S configurations

What reaction is this?

Hydration

• Uses H3O+ as a catalyst and H2O

• Tertiary carbons react the fastest

What reaction is this?

Oxymercuration-Demurcuration

• Hydration reaction

• Uses Hg(OAc)2, H2O, and NaBH4

• Forms Markovnikov product

• Can use MeOH or EtOH instead of H2O

What reaction is this?

Hydroboration Oxidation

• Hydration reaction

• Uses BH3 THF, H2O2, and NaOH

• Does SYN addition

• Add OH to lower substituted carbon —> H2O2 present

What reaction is this?

Hydrogenation

• Uses H2 and Pt

• Does SYN addition

What reaction is this?

Halogenation

• Uses 2 halides (not F or I)

• Does ANTI addition

What reaction is this?

Ozonolysis

• Uses O3 and DMS

• Cuts double bond out and caps it with an O