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An alcohol [A] with molecules formula (C...

An alcohol [A] with molecules formula `(C_(4)H_(10)O)` o oxidation with aciddified potassium dichromate gives acid [B] `(C_(4)H_(8)O_(2))`. Compound [A] when dehydrated with conc. `H_(2)SO_(4)` at `443 K` gives compound [C]. Treatment of [C] with aqueous `H_(2)SO_(4)` gives compound [D] `(C_(4)H_(10)O)` which is an isomer of [A]. compound [D] is resistant to oxidation but compound [A]can be easily oxidised. Identify [A], [B], [C] and [D]. Name the type of isomerism exhibited by [A] and [D].

Text Solution

Verified by Experts

A : `(CH_(3)_(2) CHCH_(2)OH` B: `CH_(3) CH (CH_(3)) COOH`
C: `(CH_(3))_(2) C = CH_(2)` D: `(CH_(3))_(2) - C - OH`
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A neutral organic compound X of molecualr formula C_(2)H_(6)O on oxidation with acidified potassium dichromate gives an acidic compound Y. Compound X reacts with Y on warming in the presence of conc H_(2)SO_(4) to give a sweet smelling substance Z.What are X,Y and Z?

A compound [A] with molecular formula C_(4)H_(10)O reacts rapidly with metallic sodium but very slowly with Lucas reagent. When [A] treated with hot concentrated H_(2)SO_(4) , it gives a compound [B] C_(4)H_(8) which upon hydration with aqueous H_(2)SO_(4) forms a compound [C] with molecular formula C_(4)H_(10)O . The compound [C] is almost unert to metallic sodium but reacts rapidly with Lucas reagent. What are the compounds [A], [B] and [C] ? Explain the reaction involved.

Knowledge Check

  • An optical active alcohol of formula C_(4)H_(10)O on oxidation given which of the following compound?

    A
    `(CH_(3))_(2)CHCHO`
    B
    `(CH_(3))_(2)C=CH_(2)`
    C
    `CH_(3)COC_(2)H_(5)`
    D
    `CH_(3)CH_(2)CH_(2)CHO`

  • An alcohol (A) C_4H_(10)O on oxidation with acidified K_2Cr_2O_7 gives a carboxylic acid (B) C_4H_8O_2 . (A) on treatment with conc. H_2SO_4 produces (C) C_4H_8 . (C) on treatment with dil. H_2SO_4 gives (D) C_4H_(10)O . The compound (D) is isomeric with compound (A). Compound (D) resist oxidation . What are (A) and (D) respectively ?

    A
    `CH_3CH_2CH_2CH_2OH and (CH_3)_3OH`
    B
    `(CH_3)_3COH and CH_3CH_2CH_2CH_2OH `
    C
    `(CH_3)_2CHCH_2OH and CH_3CHOHC_2H_5`
    D
    `(CH_3)_2CHCH_2OH and (CH_3)_3COH`

  • The compound F(C_(6)H_(12)O) on oxidative ozonolysis yirlds acetic acid and a compound (G) (C_(4)H_(8)O_(3)) . The new compound (G) on heating gives:

    A
    B
    `Me-CH=C=CH-Et`
    C
    D

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