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[A] underset(250^(@)C)overset(Al(2)O(3))...

`[A] underset(250^(@)C)overset(Al_(2)O_(3))(rarr) [B] underset((ii) AgOH)overset((i) HI)(rarr) [C] underset(250^(@)C)overset(Al_(2)O_(3))(rarr) [B] underset((ii) H_(2)O_(2)//OH^(-))overset((i) B_(2)H_(6))(rarr) [A]`
In the above reaction scheme [A] and [C] are isomers. [B] has a formula `C_(5)H_(10)` which can also be obtained from the product of the reaction of `CH_(3)CH_(2)MgBr` and `(CH_(3))_(2)CO`. Give the structures of [A], [B] and [C].

Text Solution

Verified by Experts

(i) The compound [B] with the formula `C_(5)H_(10)` can be prepared from `CH_(3)CH_(2)MgBr` and `(CH_(3))_(2)CO` as follows :
`underset("Propanone Ethyl mag. bromide")(CH_(3)-underset(CH_(3))underset(|)overset(O)overset(||)(C)+CH_(3)CH_(2)MgBr) rarr underset("Addition compound")([CH_(3)-underset(CH_(3))underset(|)overset(OMgBr)overset(|)(C)-CH_(2)CH_(3)])overset(H_(2)O //H^(+))(rarr)underset([C])(CH_(3)-underset(CH_(3))underset(|)overset(OH)overset(|)(C)-CH_(2)-CH_(3)) underset("2-Methylbut-2-ene [B]")(overset(-H_(2)O)(rarr)CH_(3)-underset([C_(5)H_(10)])underset(CH_(3))underset(|)(C)=CH-CH_(3))`
(ii) Since [B] has been formed by the dehydration of [C] with `Al_(2)O_(3)`, the compound [C] is a tertiary alcohol and is isomeric with secondary alcohol [A]. Both [A] and [C] cab be represented as :
`underset([C])underset("2-Methylbutan-2-ol")(CH_(3)-underset(CH_(3))underset(|)overset(OH)overset(|)(C)-CH_(2)-CH_(3))" "underset([A])underset("3-Methylbutan-2-ol")(CH_(3)-underset(CH_(3))underset(|)(CH)-underset(OH)underset(|)(CH)-CH_(3))`
(iii) Starting from [A], the sequence of reactions may be shown as follows :
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(A) underset(523K)overset(Al_(2)O_(3))(rarr)(B)underset((i)AgOH)overset((ii)HI)(rarr)(C ) underset(423K)overset(Al_(2)O_(3))(rarr)(B)underset((ii)H_(2)O_(2),OH^(-))overset((i)B_(2)H_(6))(rarr)(A) In the above reactions scheme (A) and (C ) are isomers. (B) has a fomula of C_(5)H_(10) , which can also be obtained from the product of the reactions of CH_(3)CH_(2)MgBrCO . GIve structures of (A),(B) and (C ) . So, underset((A))(CH_(3)-overset(CH_(3))overset(|)(C)H-underset(OH)underset(|)(C)H-CH_(3))underset(523K)overset(Al_(2)O_(3))(rarr)underset((B)C_(5)H_(10))(CH_(3)-overset(CH_(3))overset(|)(C)=CH-CH_(3))underset((ii)AgOH)overset((i)HI)(rarr)underset((C))(CH_(3)-underset(OH)underset(|)overset(CH_(3))overset(|)(C)-CH_(2)CH_(3))underset(423K,(-H_(2)O))overset(Al_(2)O_(3))(rarr)underset((B))(CH_(3)-overset(CH_(3))overset(|)(C)=CHCH_(3))underset((ii)H_(2)O_(2),OH^(-))overset((i)B_(2)H_(6))(rarr) CH_(3)-overset(CH_(3))overset(|)(C)H-underset(OH)underset(|)(C)H-CH_(3)

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Knowledge Check

  • (A)underset(250^@C)overset(Al_2O_3)to(B)underset((ii)AgOH)overset(HI)to( C)underset(150^@C)overset(Al_2O_3)to(B)underset((ii)H_2O_2, OH^(-))overset((i)B_2H_6)to(A) In the above reaction sequence (A) and ( C) are isomers.Molecular formula of B is C_5H_10 .which can also be obtained form the product of the reaction with CH_3CH_2MgBr and (CH_3)_2CO are followed by acidification. Identify the structure of B

    A
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    C
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