Identify the product A and product B in the following set of reactions. [figure]
- A - CH3CH2CH2-OH B - CH3 OH |CH-CH3
- A - CH3- OH |CH-CH3 B - CH3CH2CH2-OH
- A - CH3CH2CH2-OH B - CH3CH2CH2-OH
- A - CH3CH2CH3 B - CH3CH2CH3
Answer
(2) A - CH3- OH |CH-CH3 B - CH3CH2CH2-OH
Solution
A: hydration with H2O/H+ follows Markovnikov's rule, through the more stable 2° carbocation:
CH3-CH=CH2 H+ CH3- +CH-CH3
[-H+]H2O CH3- OH |CH-CH3, so A is propan-2-ol.
B: hydroboration–oxidation gives the anti-Markovnikov alcohol (B adds to the terminal C and is then replaced by OH):
3CH3-CH=CH2 (BH3)2 (CH3CH2CH2)3B
H2O2, OH 3CH3CH2CH2-OH, so B is propan-1-ol.
Answer: (2)