Given below are two statements : In the light of the above statements, choose the correct answer from the options given below
- Statement I is false but Statement II is true
- Statement I is true but Statement II is false
- Both Statement I and Statement II are true
- Both Statement I and Statement II are false
Answer
(2) Statement I is true but Statement II is false
Solution
Statement I: In vinyl chloride the lone pair of Cl is in resonance with the C=C bond:
CH2=CH- Cl: CH2-CH= Cl
so the C–Cl bond gets partial double bond character. Also the carbon is sp2 hybridised (more s-character, more electronegative) and holds Cl more tightly than the sp3 carbon of CH3-CH2-Cl. Hence the C–Cl bond is shorter and stronger in CH2=CH-Cl, and Statement I is true.
Statement II: The given compound (2-chloro-2-phenylbutane) is a tertiary benzylic halide, so it is hydrolysed by the SN1 mechanism through a planar, resonance-stabilised benzylic carbocation C6H5 C(CH3)C2H5.
Water attacks this planar carbocation equally from both faces, giving equal amounts of the two enantiomers of 2-phenylbutan-2-ol (racemisation). The racemic mixture formed is optically inactive and does not rotate plane polarised light, so Statement II is false.
Answer: (2)