Exam 3

Question 1

What does hydrohalogenation do?

Answer 1

adds a H + X
Halogen is added to Markovnikov side
forms a carbocation intermediate
can form multiple products (racemic)

Question 2

What reagents can cause a hydrohalogenation reaction to occur in a Markovnikov manner?

Answer 2

H-X (X is a halide)- Markovnikov

Question 3

What reagent to use to form the anti-Markovnikov product using hydrohalogenation?

Answer 3

1. H-X
2. ROOR (R-tBu)

Question 4

What are the steps for an anti-Markovnikov product using hydrohalogenation?

Answer 4

1. Initiation- O-O single bond from ROOR is broken, forms two radicals
2. Hydrogen-atom abstraction- one radical and an electron from the H-X bond forms a O-H bond and a radical on the halogen
3. Radical addition- an electron from the alkene and the halide forms a bond
4. Hydrogen-atom abstraction- the remaining radical on the alkene and another H-X electron adds a H to the alkane.

Question 5

Where is the radical in hydrohalogenation?

Answer 5

p-orbital, sp2 hybridized, planar

Question 6

Can radicals undergo rearrangement?

Answer 6

no

Question 7

Can H-atom abstraction in hydrohalogenation occur on top/bottom face?

Answer 7

yes, racemic products occurs

Question 8

What does hydration do?

Answer 8

adds a H-OH bond

Question 9

What are the three types of hydration and which product do they form?

Answer 9

Acid catalyzed hydration- Markovnikov
Oxymercuration-dimercuration- Markovnikov
Hydroboration-oxidation- anti-Markovnikov