Mechanism of Reactions

What is hydro halogenation?

• The Addition of H & Br across an alkene (Also works with HCl, HBr, HI)

• Follows Markovnikov Addition unless in Peroxide

• Racemic Mixture

What is Acid Catalyzed Hydration?

• Components of Water (H & OH) added acros π bond

• Follows Markovnikov Addition

• Racemic Mixture

What other acids are used in Acid Catalyzed Hydration?

• H₃O⁺

• H₂SO₄/H₂O

• H⁺/H₂O

What is Oxymecuration-Demurcuration?

• The use of mercury acetate to prevent rearrangements in addition of H & OH

• Can be Markovnikov Addition & Anti-markovnikov Addition

• No rearrangement-Occurs

• Arranged in Anti-Fashion

What is Hydroboration-Oxidation?

• Utilizing one BH₃ with three equivalent alkenes to add H&OH in a stereoselective fashion

• Follows Antimarkovnikov Addition

• H & OH are added in SYn Fashion, 2 Chiral centers formed

What is Catalytic Hydrogention?

• The use of a metal catalyst to add two H’s (H₂) across an alkene

• Syn addition only

What type of metals are used in a Catalytic Hydrogenation?

• Pb

• Ni

• Rh

• Pd/C

What is the Hydrohalogenation Anti-Markovnikov?

The addition of a H and Halogen in an Anti Markovnikov fashion.

What is Hydrohalogenation Benzene Exception?

• Bronsted acids do not cross a C=C bond in benzene

• The π electrons that would be used to form a new bond to H are too heavily stabilized by delocation

What is an Anti Dihydroxylation?

• Anti addition of OH & Oh across a π bond

• Telltale sign of reaction is peroxyacetic acid or meta-chloroperoxybenzoix acid (MCPBA)

What is an Anti-addition Halogenation?

• Anti addition of teo halogen atoms across a C=C double bond

• only practical with Br₂ and Cl₂

• Stereospecific

What is a Halohydrin Formation?

• Water acts as nucelophile that attacks the brominium ion

• Only occurs in water

• Nucleophile attacks more substituted carbon & opposite brominium ion.

What are other possible nucleophiles in Halohydrin Formation?

• Alcohols

• Amines

• Thiols

What is syn Dihydroxylation?

• Adds OH & OH across π bond in concerted fashion

• Syn addition

• Requires oxidant: NMO or Peroxide

What is Ozonolysis?

Ozone adds across double bond & cleaves alkene to form Carbonyls

What are the products of an Oxidative Ozonolysis Workup?

Peroxide create Ketones and Carboxylic Acid

What are the products of a reductive Ozonolysis Workup?

Anything other than Peroxide creates Ketones and Aldehydes.

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What is the following intermediate come from?

Halogenation or Halohydrin Mechanism

What is the following intermediate come from?

Anti Dihydroxyaltion

What is the following intermediate come from?

Oxymercuration Demercuration

What is the following intermediate come from?

Hydroboration Oxidation

What is the following intermediate come from?

Syn Dihydroxylation

What is the following intermediate come from?

Ozonolysis cyclo-addition Intermediate