alkene reactants/ reactions

what side of the molecule does the H+ add on to

the least substituted side (less amount of carbons)

hydrohalogenation: HCL, HBr, HI result in what product?

additional if both h and the halogen x; h in less substituted and x in most subst.; markovnikov rule

acid catalyzed hydration: H2SO4, H2SO4/H2O, H3O+

adding H and OH; h added to less substituted side oh added to more substituted mark.

oxymercuration-demercuration: (1) Hg(OAc)2, H2O/ (2) NaBh4

adding an H and OH (mark); H adds to less substituted side

1) HgOAc adds to both carbons (on double bond)

water attacks sp3 carbon (most bonded (3 single bonds)); oxygen attaches

add second water molecule to deprotenate (turn the h2o into oh)

2) NaBH4 just adds a hydrogen in replacement of HgOAc

hydroboration- oxidation: BH3, THF/ H2O2, NaOH

adds an h and oh; ANTI MARK

1) B attaches to LESS substituted side; a hydrogen breaks off the b as well and goes to the other side of bond

= end up with bh2

• transition state: draw potentials (dotted lines) for the double bond and connection of h and bh2

2) after having bh2, create b attached to 3 separate propyl groups (photo attached)

replace them all with oh’s using h2o2, naoh reactants

acid catalyzed alcohol addition: H2SO4/CH3OH

adding an h and an OR group ( or is oxygen and methyl)

same steps as acid catalyzed hydration

end product = OCH3 instead of a plain OH

alkoxymercuration-demercuration: (1) Hg(OAc)2, CH3OH/ (2) NaBH4

adding H and OR; MARK; sane mechanism as oxymercuration

catalytic hydrogenation: H2/Pd

adding 2 h’s

halogenation: X2/CCl4 or CH2Cl2

adding both halogens to both sides if the double bond

halohydrin formation: X2/H2O or ROH

adding halogen and oh molecule; MARK (halogen on LESS substituted side)

epoxidation & antidihydroxylation: (1) mcpba/ (2) H3O

(mcpba photo attached)

epoxide= hexane ring with o attached to 2 carbons

dihyd. = two oh molecules on OPPOSITE SIDES OF EACH OTHER

syn-dihydroxylation: (1) OsO4/ (2) NaHSO3 and KMnO4/NaOH

adding 2 oh molecules on the SAME SIDE