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The main product in the dehydration of :...

The main product in the dehydration of :
`(CH_(3))_(3) C underset(OH)underset(|)(CH)CH_(2)CH_(3)` in the presence of conc. `H_(2)SO_(4)` at `170^(@)C` is :

A

`(CH_(3))_(3) C CH = CHCH_(3)`

B

`(CH_(3))_(2)C = underset(CH_(3))underset(|)(C)CH_(2)CH_(3)`

C

`(CH_(3))_(2)CH underset(CH_(3))underset(|)(C) = CHCH_(3)`

D

`(CH_(3))_(3)C CH_(2)CH = CH_(2)`

Text Solution

Verified by Experts

The correct Answer is:
B
The intermediate carbocation `(CH_(3))_(3)C - underset(oplus)(CH) - CH_(2) - CH_(2)` undergoes rearrangement by methyl shift to form stable tertiary carbocation as :
`CH_(3) - underset(CH_(3))underset(|)overset(CH_(3))overset(|)(C) - underset(oplus)(CH) - CH_(2) - CH_(3) overset("Rearrangement")harr CH_(3) - underset(oplus)overset(CH_(3))overset(|)(C) - underset(CH_(3))underset(|)(CH) - CH_(2) - CH_(3)`
This carbonium ion loses `H^(+)` to form `(CH_(3))_(2) C = underset(CH_(3))underset(|)(C) - CH_(2) - CH_(3)` as the main product.
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Knowledge Check

  • The main product in the reaction of : CH_(3) - CH_(2) - underset(C1)underset(|)(CH) - CH_(3) + underset((alc.))(KOH) is :

    A
    `CH_(3) - CH = CH - CH_(3)`
    B
    `CH_(2) = CH - CH_(2) - CH_(3)`
    C
    `CH_(3) - CH_(2) - underset(C1)underset(|)(CH) - CH_(2)OH`
    D
    `CH_(3) - CH_(2) - underset(OH)underset(|)(CH) - CH_(3)`

  • The IUPAC name for the compound : CH_(3)-underset(O)underset(||)(C)-CH_(2)-CH_(2)OH is

    A
    3-Keto-1-butanol
    B
    1-Hydroxy-3-butanone
    C
    4-Hydroxy-2-butanone
    D
    2-Keto-4-butanol.

  • In the reaction : CH_(3)-underset(CH_(3))underset(|)(CH)-CH_(2)-O-CH_(2)-CH_(3)+HIoverset("Heat")(to)

    A
    `CH_(3)underset(CH_(3))underset(|)(CH)-CH_(2)OH+CH_(3)CH_(3)`
    B
    `CH_(3)underset(CH_(3))underset(|)(CH)-CH_(2)OH+CH_(3)CH_(3)`
    C
    `CH_(3)-underset(CH_(3))underset(|)(CH)-CH_(2)OH+CH_(3)CH_(3)I`
    D
    `CH_(3)-underset(CH_(3))underset(|)(CH)-CH_(2)-I+CH_(3)CH_(2)OH`

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    The end product of the reaction , CH_(3)underset(O)underset(||)(C)CH_(2)CH_(2)CH_(2)COOHunderset(H_(2)O,H^(+))overset(NaBH_(4))to is :

    The IUPAC name of the compound : CH_(3)-CH_(2)-underset(OCH_(3))underset(|)(C)=O is :

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