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Hydrocarbon (A) C(6)H(10), on treatment ...

Hydrocarbon (A) `C_(6)H_(10)`, on treatment with `H_(2)//Ni, H_(2)`/ Lindlar's catalylst and Na/liquid `NH_(3)` forms three different reduction products (B), ( C) and (D) respectively. (A) does not form any salt with ammoniacal `AgNO_(3)` solution, but forms a salt (E) on heating with `NaNH_(2)` in an inert solvent. Compound (E) reacts with `CH_(3)I` to give (F). Compound (D) on oxidative ozonolysis gives n-butanoic acid along with other product.
Give structures of (A) to (F) with proper reasoning.

Text Solution

Verified by Experts

The given compound (A) is `CH_3-CH_2-CH_2C-=C-CH_3` which can be confirmed by the following reactions.
(i)
(ii) (A) is non-terminal alkyne as it does not form salt with ammoniacal silver nitrate.
(iii) (A) forms (E) with `NaNH_2` which reacts with `CH_3l` to give (F).
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