Home
Class 12
CHEMISTRY
Hydrocarbon (X), C(7)H(12), on reaction ...

Hydrocarbon (X), `C_(7)H_(12)`, on reaction with boron hydride followed by treatment with `CH_(3)COOH` yields (A). On reductive ozonolysis (A) yields a mixture of two aldehydes, (B) and (C ). Of these, only (B) can undergo Cannizzaro reaction. (A) exists in two geometrical isomer, `(A-1)` and `(A-2)`, of which `(A-2)` is more stable. Gives structures of (X), (A), (B), (C ), `(A-1)`, and `(A-2)` with proper reasoning.

Text Solution

Verified by Experts

From formula `C_(7)H_(12)`, it seems to be an alkyne, which forms alkene on hydroboration. Since alkene forms two aldehydes B & C on reductive ozonolysis. Out of which B can undergo Cannizzaro.s reactive, it means that aldehyde B has no `alpha`-H atom and the -CHO group is linked to tertiary butyl group. Hence hydrocarbon X has to be
`underset((X))(CH_(3)-overset(CH_(3))overset(|)underset(CH_(3))underset(|)(C)-C-=C-CH_(3))overset((i)B_(2)H_(6))underset((ii)CH_(3)COOH)tounderset((A))(CH_(3)-overset(CH_(3))overset(|)underset(CH_(3))underset(|)(C)-CH=CH-CH_(3))overset("Reductive")underset("ozonolysis")tounderset((B))(CH_(3)-overset(CH_(3))overset(|)underset(CH_(3))underset(|)(C)-CHO)+underset((C))(O=CH-CH_(3))`
Compound B has no `alpha`-H atom hence it undergoes Cannizzaro.s reaction.
The alkene A gives two geometrical isomers, these are cis and trans.
Promotional Banner

Similar Questions

Explore conceptually related problems

Two isomeric compounds, (A) and (B), have the same formula, C_(11)H_(13)OCI . Both are unsaturated, yield the same compound (C) on catalytic hydrogenation, and produce 4-chloro-3-ethoxybenzoic acid on vigorous oxidation. (A) exists in geometrical isomers, (D) and (E), but not (B). Give structures of (A) to (E) with proper reasoning.

C_(11)H_(16) (A) reacts with two equivalent of H_(2) and on reductive ozonolysis gives two equivalent formaldeyde and (B) of the following structure. Identify structure of (A).

(A) overset(O_(3))underset(Zn//AcOH)to(B) +(C ) C_(7)H_(14) Compound (A) exist in geometrical isomers and (B) Cannizaro reaction. (A) will :

An organic compound (A) (C_(6)H_(10)O) on reaction with CH_(3)MgBr followed by acid treatment gives compound (B). The compound (B) on ozonolysis gives compound (C ), which in the presence of a base gives 1-acetyl cyclopentane (D). The compound (B) on reaction with HBr gives compound (E ). Write the structures of (A), (B), (C ), (D), and (E ). Show how (D) is formed from (C ).

An alkene (A) with molecular formula C_(5)H_(10) undergoes ozonolysis to form two aldehydes "(X)" and "(Y)" in which "(X)" contains four carbon atoms.Another "alkene (B) which is an isomer of (A) undergoes ozenolysis to form two aldehyde (C) and (D) in which (C) contain "3" carbon atoms.Identify "(X),(Y),(A)," (B) , (C) and (D).Write the reactions involved

An organic compound (A) (C_(6)H_(10)) on reaction with CH_(3)MgBr followed by acid treatment gives compound (B). The compound (B) on ozonolysis gives compound (C ), which in the presence of a base gives 1-acetylcyclo-pentene (D). The compound (B) on reaction with HBr gives (E ). Write the structures of (A), (B), (C ), and (E). Show how (D) is formed form (C ).