Reactions of AlkenesBy: Isman Kurniawan

Monday, July 21, 14

Electrophilic Addition to Alkenes

Mechanism

Monday, July 21, 14

Addition of Hydrogen Halides to Alkenes Markovnikovs rule Mechanism

Monday, July 21, 14

Addition of Hydrogen Halides to Alkenes Markovnikovs rule

Monday, July 21, 14

Addition of Hydrogen Halides to Alkenes

Markovnikovs ruleThe addition of proton acid to double bond of an alkene result in a product with the acid proton bonded to the carbon atom that already hold the greater number of hydrogen atoms.

Monday, July 21, 14

Exercise

Predict the major products of the following reactions.

Monday, July 21, 14

Addition of Hydrogen Halides to Alkenes Free radical addition: Anti-Markovnikov

addition

Mechanism

Monday, July 21, 14

Addition of Hydrogen Halides to Alkenes Mechanism

Monday, July 21, 14

Addition of Hydrogen Halides to Alkenes Free radical addition: Anti-Markovnikov

addition

Monday, July 21, 14

Exercise

Predict the major products of the following reactions, and propose mechanism to support your predictions.

Monday, July 21, 14

Addition of Water: Hydration of Alkenes Mechanism

Monday, July 21, 14

Addition of Water: Hydration of Alkenes Mechanism

Monday, July 21, 14

Addition of Water: Hydration of Alkenes Rearrangement

Monday, July 21, 14

Exercise

Predict the products of the following hydration reactions.

Monday, July 21, 14

Addition of Halogens to Alkenes

Mechanism

Monday, July 21, 14

Formation of Halohydrins

Halohydrin : an alcohol with halogen on the adjacent carbon atom

Mechanism

Monday, July 21, 14

Formation of Halohydrins

Mechanism

Monday, July 21, 14

Exercise

Predict the major product(s) for each reaction. Include stereochemistry where appropriate

Monday, July 21, 14

Catalytic Hydrogenation of Alkenes

Mechanism using heterogeneous catalyst

Monday, July 21, 14

Epoxidation of Alkenes

Epoxide : three-membered cyclic. An alkene is converted to an epoxide by a

peroxyacid

Monday, July 21, 14

Epoxidation of Alkenes

Mechanism

Monday, July 21, 14

Epoxidation of Alkenes

Consequence of concerted reaction

Monday, July 21, 14

Exercise

Predict the products, including stereochemistry where appropriate, for the m-chloroperoxybenzoic acid epoxidations of the following alkenes

Monday, July 21, 14

Acid-Catalyzed Opening of Epoxides

Mechanism

Monday, July 21, 14

Acid-Catalyzed Opening of Epoxides

Mechanism

Monday, July 21, 14

Syn Hydroxylation of Alkenes

Mechanism of Permanganate hydroxylation

Monday, July 21, 14

Exercise

Predict the major products of the following reactions, including stereochemistry.

Monday, July 21, 14

Oxidative Cleavage of Alkenes

Cleavage by permanganate condition: the solution is warm or acidic

or too concentrated

Monday, July 21, 14

Oxidative Cleavage of Alkenes

Ozonolysis

Monday, July 21, 14

Exercise

Give structures of the alkenes that would give the following products upon ozonolysis reduction

Monday, July 21, 14

Oxidative Cleavage of Alkenes

Comparison of permanganate cleavage and ozonolysis

Monday, July 21, 14