O Chem 3

markovnikov

X goes on more substituded carbon

H-X

H and X, markovnikov

H3O+/H2O or H2O/H2SO4

markovnikov, OH and H, move double bond toward teritary carbon if there is one

Hg(OAc)2, H2O/NaBH4

markovnikov, OH and H, no stero

antimarkovnikov

X goes on least subsituted carbon

Br2

Br and Br, trans

Br2 and H2O

Br and OH, trans

CHCl3 and KOH

triangle with 2 Cls

mCPBA

triangle O, trans for CH3’s if up and down, cis for both in one direction

BH3 then H2O2, OH-

OH and H, cis

O3 then me2S

double bond O and double bond O

H2 then Pd/C or catalyst

H and H, cis

OsO4/NMO then H2O

OH and OH, cis

1. mCPBA 2.H3O+

OH and OH, trans

1. O3, -78 C 2. Zn, CH3CO2H

2 products, double bond O replaces C in each

Triple bond

NaNH2 then CHCHBr (Br replaces C)

H2, Lindars

triple to double, H on each side

9-BBN then H2O2/NaOH

triple to single, double bond O on side with H

H2SO4, H3SO4, H2O

triple to single, double bond O on a C

2 Na then liquid NH3

triple to double, H on each end

If X is placed on chiral center

show stereochemistry

when weird shape

no stereochemistry

allyl

C-C=C

single bond

ane

double bond

ene

triple bond

yne

2 bouble bonds

dien

3 double bonds

trien

4 double bonds

tetraen

unsaturations

(C-1) - (H+ halogen- N)/2

squares stability

not on ring

rings stability

more substituted

skeletal stability

trans and closer double bonds

alkynes are ___ than alkenes

less stable and more reactive

name of idea that justifies use of cations

Hammond Postulate

equilibrium constant

10^(product-reactant)

pKa of triple bond

25

NH3 pKa

33

OH2 pKa

15.7