Rf value for 2-methylpropene in a solvent system (Ethyl acetate + ether) is 0.42. 2-methylpropene is treated with dilute H2SO4 to give major organic product (X). Rf value for (X) in the same solvent system under identical condition will be:
- 0.42
- 0.82
- 0.62
- 0.12
Answer
(4) 0.12
Solution
Acid-catalysed hydration follows Markovnikov's rule (via the 3° carbocation):
(CH3)2C=CH2 + H2O H+ (CH3)3C-OH
⇒ X = 2-methylpropan-2-ol (tert-butyl alcohol)
Rf = distance moved by the substance from base linedistance moved by the solvent from base line
X has a polar –OH group (hydrogen bonding) ⇒ it is adsorbed more strongly on the polar stationary phase than the non-polar alkene ⇒ it moves less
⇒ Rf(X) < 0.42; among the options only 0.12 is smaller
Answer: (4)