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(C(6)H(12))overset(HCl)rarr underset((C(...

`(C_(6)H_(12))overset(HCl)rarr underset((C_(6)H_(13)Cl))(B)+(C )`
`(B)overset(Alc.KOH)rarr(D)` [isomer of (A)]
`(D)overset("Ozonolysis")rarr(E )` (It gives negative test with Fehling's solution but responds to iodoform test)
`(A)overset("Ozonolysis)rarr(F)+(G)` (Both give positive Tollens test but do not give iodoform test)
`(F)+(G)overset("Conc.NaOH)rarr HCOONa` + A primary alcohol .
Identify A to G.

Text Solution

Verified by Experts

Both (G) and (G) are aldehydes having no `alpha`-H atom because they undergo cross Cannizzaro reaction and they give positive Tollen' test. One aldehyde is (HCHO), since one product of Cannizzaron reaction is HCOONa
Total carbon atom in (A) are sixand ozonolysis, product, of (A) is HCHO an a fie carbon aldehyde ahving no `alpha` H atom . So, another aldehyde must be `(Me)_(3)` C-CHO
Therfore, the structure of compound (A) is : (Proceed revers)
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OP TANDON-ALDEHYDES AND KETONES -PROBLEMS BASED ON STRUCTURE AND PROPETIES
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  2. A ketone (A) give iodoform on reacting with iodine and sodium hydroxid...

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  3. An organic compound (A) adds Br(2) to give C(5)H(8)Br(2) O. It does no...

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  4. Two organic compounds (A) and (B) with molecular formula, C(3)H(6)O, r...

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  5. A compound has molecular formula C(6)H(12)O. It does not reduce Tollen...

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  6. A organic compound (A) obtained by the hydrolysis of dichlorobutane, g...

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  7. An organic compound having molecular formula C(5)H(10)O exixts in two ...

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  8. An organic compund (A) having molecular formula C(4)H(8), decolourises...

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  9. An organic compound (A) having molecular formula C(5)H(10)O can show v...

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  10. A hydrocarbon (A) of the formula C(7)H(12) on ozonolysis gives a compo...

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  11. An organic compound (A) (C(6)H(10)O) on reaction with CH(3)MgBr follow...

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  12. An alkene, C(6)H(12), after ozonolysis yielded two products. One of th...

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  13. Compound (A), C(5)H(10)O, forms a phenylhdrazone, gives regative Tolle...

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  14. Compound (A), having an empirical fomrula C(7)H(8), is chlorinated in ...

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  15. (C(6)H(12))overset(HCl)rarr underset((C(6)H(13)Cl))(B)+(C ) (B)overs...

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  16. Five isomeric para-disubsituted atomatic compounds (A) to ( E) with mo...

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  17. An aromatic kentone (X) has the molecular formula C(10)H(12)O(2). On v...

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