Recitation notes:

Cyclic alkene w/N & CH3;Br displaces the N;H2O displaces the CH3

3 hydrations:

1. acid water
2. oxymercuration
3. ??

xx??

1. Add H+ (in Mark. Sense)
2. What kind of C+? 3deg = no rearrangement
3. can you make more stable C+ by moving H or C from adjacent C

You can have a 1,2 alkele shift

You don't want to end up with a primary carbon cation (end C is +)

"onium" compounds use 1 nonbonded e- pair to make an additional bond

• eg NH3+ +H+ -> NH4+
• eg H2O + H+ -> H3O+
• eg CH4 + H+ -> CH5+
• a carbonium ion:
  • H3CBr -> H3C+ + Br-

Book does not talk about alcohol -> alkene reaction, but we are responsible for it.

In water (OH-) = 0.000001Molar; [H2O] = 55 Molar

transition metals are the biggest advance in the last 10-20 years in organic chemistry

2 Step alkene reactions

1. Mercuric acetate in water
2. Sodium in water
3. Hycroxylation

HgOAr3,H2O

NaBHy

OsO4

NaHSO3…KMnO4 Hydroxillation

1. O3
2. Zn/H3O+

"Fullerene" (Bucky Balls)

• C60, with double bond; + OsO4 yields a Osmonium 'side ring' on the Bucky Ball

2-hexene will give a mixture of products; CCOHCCCC & CCCOHCCC

Which alkene would you use to make CCOHCCCC and which reactions?

1. 1-hexene
2. any of the Markonikov reactions (H3O+), (mercury oxidation)

want to make cis-2-methyl cyclohexane

1. BH3
2. H2O2

• Can we do it?
• What are the reactions?
• What do we start with?
  • requires hydroboration hydration

Sterio chemistry