orgo rnx

halohydrogenation

H-X added

X adds markovnikov

No sterochem

halohydrogenation mechanism

H+ transfer rearrange if possible then nu attack of X to most substituted carbon

anti-markovnikov halohydrogenation

H-X

X adds anti markovnikov

No stereochem

anti-markovnikov halohydrogenation mechanism

H+ transfer and H add to more substituted carbon so carbon cation is on less substituted carbon and then nu attack of X- on the less substituted carbon cation

acid catalyzed hydration

H and OH

OH adds markovnikov

No stereochem but rearrangement can occur

H+/H2O or H3O+ or H2SO4 dilute

adds H and OH at more substituted spot with rearrangement

acid catalyzed hydration mechanism (H+/H2O or H3O+ or H2SO4 dilute)

H+ transfer and H2O attacks more substituted carbon cation and then H+ transfer on H2O

oxymercuration/demercuration

H and OH

OH adds markovnikov

No sterochem

Hg(Oac)2 H2O / NaBh4

adds H and OH at markovnikov but no rearrangement

oxymercuration/demercuration mechanism (Hg(Oac)2 H2O / NaBh4)

first double bond nu attacks the Hg at less substituted side and 1 OAc has LG loss and the lone pair on Hg nu attack the carbon cation then H2O nu attacks the carbon cation and LG loss of positive Hg-OAc then H2O H+ transfer then NaBH4 somehow removes Hg-OAc so then just OH on more substituted side

hydroboration/oxidation

H and OH

OH adds anti markovnikov

Stereo Yes adds syn

BH3 / H2O2 NaOH

adds OH on less substituted side and has same wedge/dash as H “syn”

hydroboration/oxidation mechanism (BH3 / H2O2 NaOH)

BH3 on less substituted carbon and then one H attaches to the more substituted carbon and then BH2 on less substituted side interacts with H2O2 and NaOH and OH replaces the BH2

catalytic hydrogenation

H and H

No regio

Stereocehm is syn addition

H2 / Pt

adds Hs with same sterochem '“syn”

catalytic hydrogenation mechanism (H2 / Pt)

the alkene interacts with Pt that have hydrogens on it then it breaks the double bond and uses that to create bonds with two Hs and the gets syn H attachments

halogenation

X and X

No regio

Stero yes Xs add anti

X2

adds X on each side of double bound with trans stereochem

halogenation mechanism (X2)

double bond Nu attack on X at less substituted carbon cation and other X LG loss then lone pair on X attacks carbon cation then the free X- Nu attack more substituted carbon and LG loss of X+ and then creates anti product

halohydrin

X and OH

OH adds markovnikov

Stereochem anti

X2 / H2O

adds OH on more substituted and X on less

halohydrin mechanism (X2 / H2O)

Nu attack on X-X and LG of a X and X is on less substituted carbon and the lone pair of X attack carbon cation and then H2O Nu attack the more substituted carbon then H+ transfer with free X- and leaves OH

anti-dihydroxylation

OH and OH

no regio

Sterochem anti

RCO3H / H3O+ or McPBA / H3O+

OH and OH added trans

anti-dihydroxylation mechanism (RCO3H / H3O+ or McPBA / H3O+)

the RCO3H or McPBA adds O then O H+ transfer H+ from H3O+ then H2O Nu attack at more substituted carbon and LG loss of O+ then H+ transfer to leave OH

syn dihydroxylation

OH and OH

no regio

Stereo adds syn

OsO4 / NaHSO3 H2O

adds OH and OH cis

syn dihydroxylation mechanism (OsO4 / NaHSO3 H2O)

OsO4 adds 2 O on same side then interacts with NaHSO3 H2O removes the OsO2 and adds Hs on Os

ozonolysis (O3 / DMS)

breaks C=C bond and adds 2 Os double bonded to molcules