Chapter 8

antiaddition

adds from both sides (top and bottom)

synaddition

adds from same side (top or bottom)

markarmikov rule

add H to C with most H’s

addition of HX to alkenes

Markovnikov, double bond is broken, forming a cation on one of the C, the other gets the H. Then, the X attaches to where the + was.

free radical addition of HBR

presence of peroxides (ROOR), anti-markarmikov

hydration of alkenes

markarmikov, addition of water to the double bond forms an alcohol, uses dilute solutions of H2SO4 or H3PO4 to drive equilibrium toward hydration

oxymercuration demercuration reaction

markarmikov, has mercury, intermediate is a three-membered ring (mercurinium ion) not a carbocation. If the nucleophile is an alcohol (ROH), instead of water, an ether is produced

hydroboration of alkenes

anti-Markovnikov, synaddition, has boron

addition of halogens

antiaddition, intermediate is a three-membered ring (halonium ion).

catalytic hydrogenation

only takes place if a catalyst is used (catalyst + Pt, Pd, or Ni), synaddition

epoxidation

An alkene reacts with a peroxyacid (contains an -OOH group) to form an epoxide

hydroxilation of alkenes

uses OsO4 or KMnO4 and H2O2 or cold dilute, synaddition

oxidative cleavage

Uses KMnO4 and warm acidic, disubstituted carbons become ketones and Monosubstituted carbons become carboxylic acids