When dissolved in `H_(2)SO_(4)`, hexa`-1,4-dien-3-ol` is converted into

Options

A. hexa`-3`, `5-`dien`-2-`ol
B. hexa`-2`, `4-`dien`-1-`ol
C. both `(1) and `(2)`
D. `H_(2)C = C = CH - CH = CHCH_(3)`

Answer

C

Explanation

`underset(Hexa-1,4-dien-3-ol)underset(OH)underset(|)(H_(2)C=CH-CH=CH_(2))overset((i)H^(+))underset((ii)-H_(2)O)(rarr)`

`harr H_(2)overset(+)(C) - CH = underset(a)(CHCH) = CHCH_(3)`
`harrH_(2)C = CH -underset(b)(CH) =CH -overset(+)(CHCH_(3))] overset((i)H_(2)O)underset((ii)-H^(+))rarr`
`underset("Hexa-2,4-diene"-1-ol)(HOoverset(1)(CH_(2))overset(2)(CH)=overset(3)(CH)-overset(4)(CH)=overset(5)(CH)overset(6)(CH_(3)))`
`underset("Hexa-3,5-diene-2-ol")(+H_(2)overset(6)C=overset(5)(CH)-overset(4)CH=overset(3)(CH)overset(2)underset(OH)underset(|)(CH)overset(1)(CH_(3)))`
The initially formd allyl carbocation is stabilized by delocalization over an extended carbon chain having more than one `C^(delta+)` site. the double bond shift to give an allylic conjugated diene. the nucleophile `H_(2)ddot(O: )` attacks at either of two electron deficient sites to yields isomeric products