An ester (A) with molecular formula 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

Question

An ester (A) with molecular formula 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)  C6H5COOC6H5  (C)  C6H5COOCH3  (D)  p - H3CO - C6H4 -COCH3

Tardigrade Admin · Accepted Answer

undersetAC6H5COOC2H5 xrightarrowCH3MgBr

C6H5 - underset overset||OC - CH3 xrightarrow[NaOH]I2 underset textiodoformCHI3 + C6H5COONa

$C_{6} H_{5} COO C_{2} H_{5}$

$C_{6} H_{5} COO C_{6} H_{5}$

$C_{6} H_{5} COOC H_{3}$

$p$ - $H_{3} CO - C_{6} H_{4} - COC H_{3}$

$A C_{6} H_{5} COO C_{2} H_{5} C H_{3} M g B r$

$C_{6} H_{5} - O ∣∣ C - C H_{3} I_{2} N a O H$
$iodoform C H I_{3} + C_{6} H_{5} COON a$

Q. An ester (A) with molecular formula C9​H10​O2​ was treated with excess of CH3​MgBr and the complex so formed was treated with H2​SO4​ to give an olefin (B) . Ozonolysis of (B) gave a ketone with molecular formula C8​H8​O which shows positive iodoform test. The structure of (A) is

C6​H5​COOC2​H5​

C6​H5​COOC6​H5​

C6​H5​COOCH3​

p - H3​CO−C6​H4​−COCH3​

AC6​H5​COOC2​H5​​CH3​MgBr​ C6​H5​−O∣∣C​−CH3​I2​NaOH​ iodoformCHI3​​+C6​H5​COONa

$C_{6} H_{5} COO C_{2} H_{5}$

$C_{6} H_{5} COO C_{6} H_{5}$

$C_{6} H_{5} COOC H_{3}$

$p$ - $H_{3} CO - C_{6} H_{4} - COC H_{3}$

$A C_{6} H_{5} COO C_{2} H_{5} C H_{3} M g B r$

$C_{6} H_{5} - O ∣∣ C - C H_{3} I_{2} N a O H$
$iodoform C H I_{3} + C_{6} H_{5} COON a$