TIPS/Formulae :
Both compounds do not contain \[\alpha \text{-}\] hydrogen hence
undergo Crossed Cannizzaro reaction.
Initially \[\text{O}{{\text{H}}^{-}}\] attacks at the carbonyl carbon of \[HCHO\] than that of \[PhCHO\] because carbonyl carbon of \[HCHO\] is
(i) more electrophilic
(ii) less sterically hindered to give hydroxyalkoxide which acts as hydride donor in next step to give sodium formate.
\[{{C}_{6}}{{H}_{5}}CHO+HCHO\xrightarrow[{}]{NaOH}\,HCOONa+{{C}_{6}}{{H}_{5}}C{{H}_{2}}OH\]
62.
\[C{H_3} - C \equiv CH\xrightarrow[{1\% \,HgS{O_4}}]{{40\% \,{H_2}S{O_4}}}A\] \[\xrightarrow{\text{Isomerisation}}C{{H}_{3}}\underset{\begin{smallmatrix}
\parallel \\
O
\end{smallmatrix}}{\mathop{-C-}}\,C{{H}_{3}}\]
Structure of $$'A'$$ and type of isomerism in the above reaction are respectively
63.
Ketones \[(R\overset{\begin{smallmatrix}
O \\
\parallel
\end{smallmatrix}}{\mathop{-C-}}\,R')\] can be obtained in one step by ( where $$R$$ and $$R'$$ are alkyl groups )
Aldehydes and ketones form insoluble crystalline compounds with $$NaHS{O_3}$$ which can be filtered. These on distillation with saturated solution of $$N{a_2}C{O_3}$$ again give the aldehydes and ketones.
65.
In the following sequence of reaction, the final product $$(Z)$$ is \[CH\equiv CH\xrightarrow[{{H}_{2}}S{{O}_{4}}]{H{{g}^{2+}}}X\xrightarrow[{{H}_{2}}O]{C{{H}_{3}}MgX}\] \[Y\xrightarrow{\left[ O \right]}Z\]
Aldehydes which do not have any $$\alpha $$ - hydrogen atom when heated with a concentrated solution of $$NaOH$$ undergo a simultaneous oxidation and reduction (disproportionation) forming a salt of carboxylic acid and alcohol. This reaction is called Cannizaro reaction.
$$2{C_6}{H_5}CHO + NaOH \to $$ $$\mathop {{C_6}{H_5}C{H_2}OH}\limits_{{\text{Benzyl alcohol}}} + \mathop {{C_6}{H_5}CO\mathop O\limits^ - N\mathop a\limits^ + }\limits_{{\text{Sodium benzoate}}} $$
67.
An organic compound of molecular formula $${C_3}{H_6}O$$ did not give a silver mirror with Tollens' reagent but give an oxime with hydroxylamine. It may be
$$ArCOR$$ can be prepared by the combination of $$ArH + RCOCl$$ and not by $$ArCOCl + RMgX$$ because here the $$ArCOR$$ formed will further react with $$RMgX$$ to form \[{{3}^{\circ }}\] alcohol, \[ArC\left( OH \right){{R}_{2}}\] as the final products.
69.
Alkene $$\left( X \right)\left( {{C_5}{H_{10}}} \right)$$ on ozonolysis gives a mixture of two compounds $$(Y)$$ and $$(Z).$$ Compound $$(Y)$$ gives positive Fehling's test and iodoform test. Compound $$(Z)$$ does not give Fehling's test but give iodoform test. Compounds $$(X), (Y)$$ and $$(Z)$$ are