Self-condensation of two moles of ethyl acetate in the presence of sodium ethoxide yields:

  • A
    ethyl propionate
  • B
    ethyl butyrate
  • C
    acetoacetic ester
  • D
    methyl acetoacetate

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Columns $1$,$2$,and $3$ contain starting materials,reaction conditions,and type of reactions,respectively.
$Column-1$ $Column-2$ $Column-3$
$(I)$ Toluene $(i)$ $NaOH / Br_2$ $(P)$ Condensation
$(II)$ Acetophenone $(ii)$ $Br_2 / h\nu$ $(Q)$ Carboxylation
$(III)$ Benzaldehyde $(iii)$ $(CH_3CO)_2O / CH_3COOK$ $(R)$ Substitution
$(IV)$ Phenol $(iv)$ $NaOH / CO_2$ $(S)$ Haloform

$(1)$ For the synthesis of benzoic acid,the only $CORRECT$ combination is
$[A] (III) (iv) (R)$ $[B] (IV) (ii) (P)$ $[C] (I) (iv) (Q)$ $[D] (II) (i) (S)$
$(2)$ The only $CORRECT$ combination in which the reaction proceeds through radical mechanism is
$[A] (I) (ii) (R)$ $[B] (II) (iii) (R)$ $[C] (III) (ii) (P)$ $[D] (IV) (i) (Q)$
$(3)$ The only $CORRECT$ combination that gives two different carboxylic acids is
$[A] (IV) (iii) (Q)$ $[B] (III) (iii) (P)$ $[C] (II) (iv) (R)$ $[D] (I) (i) (S)$

An alkene $(A)$ $C_{16}H_{16}$ on ozonolysis gives only one product $(B)$ $C_8H_8O$. $(B)$ can also be obtained by the hydrolysis of the product obtained from the reaction between cyanobenzene and $CH_3MgBr$. $(A)$ shows geometrical isomerism and decolourises $Br_2$ water. $(B)$ on treatment with $SeO_2$ produces $(C)$. Which statement is not correct about $(B)$?

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