Orgo Exam 3

HX in Ether
Markovnikov : Adds Nin in most substituted side (follows carbocation stability)
Can't perform: with HF
Has a carbocation intermediate => indicates rearrangement

HBr, ROOR
Anti - Markovnikov
Presumably has a carbocation intermediate => indicates rearrangement
Page 2 reaction

HX in H2SO4, H2O
markovnikov
has a carbocation intermediate, indicates rearrangement

1. BH3, THF
2. H2O2, NaOH
Anti Markovnikov
Syn addition
no carbocation intermediate, no rearrangement

X2 in THF/CCl4
no carbocation intermediate
anti-addition

X2 in H20 or ROH
markovnikov, OH attacks most stable carbocation
no carbocation intermediate
anti-addition

H2, Pd/C
no carbocation intermediate
syn addition

1) Hg(OAc)2, H2O
2) NaBH4
markovnikov
no carbocation intermediate
anti-addition

1) Hg(OAc)2, ROH
2) NaBH4
Similar to oxymercuration-demercuration

RCOOOH
no carbocation intermediate
syn addition

1) RCO3H
2) H3O+
no carbocation intermediate
anti addition
Sn2-like = anti
differs between acidic and basic conditions

differs between oxidizing and reducing conditions
O3 then (CH3)3S or Zn/H2O(reducing)
O3 then H2O2 or KMnO4 or H3O
break every double bond
under oxidizing conditions, replace all H's with OH

OsO4 then H20, or KMnO4 in OH
no carbocation intermediate
syn-addition, both OH groups are added to the same side

CR2(2 R groups attached to a C, the C has no hydrogens attached)
no carbocation intermediate
syn addition, both bonds to carbon on the same side

HX in ether
1st halogen adds to the most substituted carbon (markovnikov)
2nd halogen adds to the 1st halogen's carbon

HX in H2O
markovnikov, initial carbocation goes onto most substituted carbocation
markovnikov's rule is only relevant for terminal alkynes

X2
2 products are formed when only 1 X2
the trans product is the major product

Hg(OAc)2 in H2O, then acid
markovnikov
only relevant for terminal alkynes