An ester (A) with molecular fomula, C₉H₁₀O₂ was treated
with excess of CH₃MgBr and the complex so formed was
treated with H₂SO₄ to give an olefin (B). Ozonolysis of (B)
gave a ketone with molecular formula C₈H₈O which shows
positive iodoform test. The structure of (A) is
(a) C₆H₅COOC₂H₅
(b) C₂H₅COOC₆H₅
(c) H₃COCH₂COC₆H₅
(d) p—H₃CO—C₆H₄ —COCH₃
Answers
The structure of A is C₆H₅COOC₂H₅.
Option (A) is correct.
Explanation:
OH
|
C6 H5 COOC2H 5 + CH3 MgBr ----------> C6 H5 − C − CH3 + H2 SO4 / Δ
|
CH3 CH3 O
| ||
-----> C 6 H 5 − C = CH2 + O 3 -----> HCHO + C 6 H 5 − C −CH3 ↓NaOI
C6H5CONa + CH3I
Thus the structure of A is C₆H₅COOC₂H₅.
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