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What is the final product of the followi...

What is the final product of the following reaction sequence?
`(CH_(3))_(3) C-C-=C-H overset((i)dil.H_(2)SO_(4)//HgSO_(4))underset({:(,(ii) NaBH_(4)//"ethanol"),(,"(iii) dil . acid"):})to`

A

`(CH_(3))_(3)C-overset(OH)overset(|)(CHCH_3)`

B

`(CH_(3))_(3)-CH=CH_2`

C

`(CH_(3))_(2)C=C(CH_3)_(2)`

D

`(CH_(3))_(3)C-CH_(2)-CH_(2)OH`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the final product of the reaction sequence given in the question, we will break down the steps involved in the reaction process. ### Step 1: Identify the Starting Material The starting material is `(CH₃)₃C-C≡CH`, which is 3,3-dimethyl-1-butyne. ### Step 2: Reaction with Dilute H₂SO₄ and HgSO₄ When 3,3-dimethyl-1-butyne reacts with dilute sulfuric acid (H₂SO₄) and mercuric sulfate (HgSO₄), it undergoes hydration. The reaction involves the formation of a carbocation. 1. The triple bond (C≡C) is converted into a double bond (C=C) by the addition of H₂O. 2. The more stable secondary carbocation is formed when the double bond is created: - The reaction proceeds through the formation of a secondary carbocation at the 2-position. - The product at this stage is 3,3-dimethyl-2-buten-1-ol (with an OH group attached to the more substituted carbon). ### Step 3: Tautomerization The product undergoes tautomerization, which involves the rearrangement of the structure to form a ketone: - The alcohol (OH) group can shift to form a carbonyl (C=O) group. - The resulting product after tautomerization is 3,3-dimethyl-2-butanone. ### Step 4: Reduction with NaBH₄ in Ethanol Next, the ketone (3,3-dimethyl-2-butanone) is reduced by sodium borohydride (NaBH₄) in ethanol: - NaBH₄ is a mild reducing agent that selectively reduces ketones to alcohols. - The final product of this reduction is 3,3-dimethyl-2-butanol. ### Final Product The final product of the reaction sequence is **3,3-dimethyl-2-butanol**. ---

To determine the final product of the reaction sequence given in the question, we will break down the steps involved in the reaction process. ### Step 1: Identify the Starting Material The starting material is `(CH₃)₃C-C≡CH`, which is 3,3-dimethyl-1-butyne. ### Step 2: Reaction with Dilute H₂SO₄ and HgSO₄ When 3,3-dimethyl-1-butyne reacts with dilute sulfuric acid (H₂SO₄) and mercuric sulfate (HgSO₄), it undergoes hydration. The reaction involves the formation of a carbocation. ...
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