OChem Chp. 8 - Alkyne and Alkene reactions

Alkane synthesis

an alkene is treated with an electrophile-neutrophile comound that adds atoms across the bonds

Markonikov’s rule

The tendency of a carbon with multiple bonds to engage in reactions, “the rich get richer”

Peroxide Mechanism

breaks an alkene through a reaction where peroxide forms radicals, bonding to hydrogen from bromic acid and leaving behind a bromine radical. Forms a radical intermediate on the compound, which will later form a bond with a hydrogen to form an alkene.

Peroxide reaction

Alkene to Alkanes, reaction of HBr and ROOR, anti-Markovnikov and forms a radical intermediate

Acid hydration mechanism

An alkene attacks hydronium to create water and a carbocation intermediate, and the water will bond to the carbocation. Another water molecule will remove one hydrogen from the water group, forming an alcohol.

Acid Hydration reaction

An alkene to an alkanyl alcohol, forms a carbocation intermediate

Oxymurcuration reaction

Alkene-to-alkanyl alcohol reaction, water on a Markovnikov site. 1. HgoAc and H2O, and 2. NaBH4

Oxymercuration reaction mechanism

HgoAC. The double bond attacks the mercury ion, which creates a cyclopropane. Water attacks the Markovnikov site, and a hydrogen leaves and bonds to the anti-Markovnikov site, causing the HgoAc to leave.

Hydroboronation

Alkene to alkanyl alcohol, syn addition, forms racemates, anti-Markovnikov

Halogen Alkene reactions

Will always be anti addition and ant Markovnikov

Halohydrin formation

Anti-addition of a base and a halogen across an alkene. Halogen with protic solvents, due to solvation, the second halogen is unable to react and instead the conjugate base of the solvent will.

Carbene

Carbon with two bonds and a lone pair, can be any molecule but commonly includes hydrogens and chlorines

Carbenation

addition of a carbene to an alkene, forming a cyclopropane

Simmons smith cyclopropination

A carbene ICH2 is added to an alkene, using Zn(Cu) to remove the I

Osmium tetroxide

Oxidation of alkenes, forming diols in syn addition. 1. OsO4, pyridine, 2. H2O, NASO3

KMnO4 oxidation Hot

KMnO4 at hot temperatures, acidic, will cleave the double bonds and form compounds based on the number of attached hydrogens: Ketones for no hydrogens, Carboxylic acid for 1, and CO2 for 2

Cold KMnO4

Will oxidise an alkene at cold or basic conditions

Ozonolosis

Cleaves the pi bonds and creates compounds based on the number of attached hydrogens. Ketone for 0, aldehyde for 1, and formaldehyde for 2

Ozone peroxide reaction

Will occur the same as a hot KMnO4 reaction

Periodic acid reaction

HIO4 will cleave vicinal dios and oxygen double bonds, replacing splits with alcohols and then grouping them together to form waters, leaving an oxygen double bond on single oxygens

epoxide

functional group involving a three membered ring of C2O, “cyclic ether”

Epoxidation

catalyzed by peroxides occur through syn addition with mCPBA as the reagent, usually forming a cyclic ether on an alkene in a concerted step, retaining the stereochemistry