Unit 8: Addition Reactions

For Unit 8 quiz and Exam 3

Hydrohalogenation (1)

HX (X = Cl, Br)

Regio: Markovnikov

Stereo: Racemization

Hydrohalogenation (2)

HBr, ROOR (peroxide)

Regio: anti-Markovnikov

Stereo: Racemization

Acid-Catalyzed Hydration

H₃O⁺

Regio: Markovnikov

Stereo: Racemization

Oxymercuration-Demercuration

1. Hg(OAc)₂, H₂O 2. NaBH₄

Regio: Markovnikov

Stereo: ANTI (H/OH)

Hydroboration-Oxidation

1. 9-BBN 2. NaOH, H₂O₂,

Regio: anti-Markovnikov

Stereo: SYN (H/OH)

Hydrogenation

H₂ + metal catalyst (Pd, Pd/C, Pt, Ni)

Regio: N/A

Stereo: SYN (H/H)

Halogenation

X₂ (usually Br₂)

Regio: N/A

Stereo: ANTI (X,X)

Halohydrin Formation

X₂, H₂O

Regio: Markovnikov (OH)

Stereo: ANTI (X, OH)

Anti-Dihydroxylation

1. m-CPBA 2. H₃O⁺

Regio: N/A

Stereo: ANTI (OH/OH)

Syn-Dihydroxylation

1. OsO₄ 2. NaHSO₃, H₂O

Regio: N/A

Stereo: SYN (OH/OH)

Oxidative Cleavage

1. O3 2. Zn, H₃O⁺

Regio: N/A

Stereo: N/A