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(A)(C(8)H(14))underset(Acidic KMnO(4))ov...

(A)`(C_(8)H_(14))underset(Acidic KMnO_(4))overset([O])(rarr)(B)+(C )+(D)`
(A) requires `2 mol` of `H_(2)` for its saturation.
(B) reduces ammoniacal `AgNO_(3)` and gives yellow colour with `NaOH+I_(2)`.
(C ) does not reduce Tollens reagent but gives iodoform test.
(D) on dehydration with conc. `H_(2)SO_(4)` gives a mixture of colourless gases.
The mixture of colourless gases is:

A

a.`CO_(2)`

B

b.`CO`

C

c.`CO_(2)+CO`

D

d.`CO_(2)+CO+H_(2)O`

Text Solution

Verified by Experts

The correct Answer is:
D
`(2Du "in" A)`. It may have either two `(C=C)` or one `(C-=C)` bond. Formation of three compounds on oxidation of (A) shows that it contains two `(C=C)` bonds. (B) reduces ammoniacal `AgNO_(3)` solution and gives iodoform test.
Therefore, (B) is an aldehyde and it is `(CH_(3)-CHO)`(two-C-atom aldehyde).
(C ) is a ketone containing `(CH_(3)-overset(O)overset(||)(C)-)` group (since it gives iodoform test).
(D) is two-C dibasic acid since it gives `CO_(2), CO`, and `H_(2)O` with conc. `H_(2)SO_(4)`. So, (D) may be oxalic acid `(HOOC-COOH)`(two C atoms). Total C atoms in (C ) must be four.
`(A) (C_(8)H_(14))impliesunderset((B))CH_(3)CHO ("two C atoms")+underset(("four C atoms"))((CH_(3)COCH_(2)CH_(3)))+(HOOC-COOH)underset((D))overset((C ))(("two C atoms"))`
Structure of `(A) implies`
Structure of (A) `implies`

Compound (D) `implies`
`HOOC-COOH overset("Conc". H_(2)SO_(4))(rarr) CO_(2)+CO+H_(2)O`
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