question_answer

Which of the following statements is correct regarding the following reaction? \[C{{H}_{3}}-C\equiv C-H\xrightarrow{Si{{a}_{2}}BH}A\xrightarrow{{{H}_{2}}{{O}_{2}}/O{{H}^{-}}}B\]

A)  Product will show tautomerism and metamerism

B)  Product will show geometrical isomerism only

C)  Product will show metamerism only

D)  None of the above

Correct Answer: A

Solution :

 Idea This problem includes a conceptual mixing of hydroboration oxidation and isomerism. Skill required to solve the problem includes command over electrophilic addition along in depth knowledge of isomerism. Hydroboration oxidation Alkene on reaction with borane produces alkyl borane which on oxidation produces alcohol. In the given reaction product B is obtained as follows \[C{{H}_{3}}-C\equiv C-H\xrightarrow{Si{{a}_{2}}BH}C{{H}_{3}}-\underset{\begin{smallmatrix}  | \\  \text{H} \end{smallmatrix}}{\mathop{C}}\,=\underset{\begin{smallmatrix}  | \\  \text{H(Sia}{{\text{)}}_{2}} \end{smallmatrix}}{\mathop{C}}\,-H\xrightarrow{{{H}_{2}}{{O}_{2}}/O{{H}^{\odot -}}}\] Tautomerism and metamerism Tautomerism is shown by a compound B. B interconverts to keto form as follows Ketone also show metamerism due to difference in nature of alkyl group present on both sides of > C= O group possible metamers of B are \[C{{H}_{3}}-\overset{\begin{smallmatrix}  O \\  || \end{smallmatrix}}{\mathop{C}}\,-C{{H}_{3}}\],\[C{{H}_{3}}-C{{H}_{2}}-\overset{\begin{smallmatrix}  O \\  || \end{smallmatrix}}{\mathop{C}}\,-H\] Structure of\[Si{{a}_{2}}BH\]is Name of\[Si{{a}_{2}}BH\]is disiamyl borane. TEST Edge Students are advised to study information relating to oxymercuration demercuration and electrophilic addition of boron hydrides with cleavage of resultant product by peroxide, coupling reagent (\[AgN{{O}_{3}}/NaOH\]) and protic agent. Hydroboration oxidation is the reaction of atmost importance as we can produce various hydrocarbons, alcohols and carboxyl compound from the reaction.