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The product of the given reaction ,...

The product of the given reaction ,
`CH_3 - underset( OH )underset( |) overset(| ) overset( CH_3 ) overset(|) C-underset(NH_2 ) underset(|) overset(CH_(3) ) overset( |) C -CH_(3) overset( HNO_2 ) to ` Product is :

A

`CH_(3) - underset(OH) underset( |) overset( CH_3)overset(|)C-underset(OH)underset(|) overset(CH_3)overset(|)C-CH_3`

B

`CH_(3) - overset(O) overset(||) C- underset(CH_3) underset(|) overset( CH_3) overset( |) C- CH_3`

C

`CH_(3) - underset( OH) underset( |) overset(CH_3) overset(|)C- underset(CH_3 )underset(|) CH-CH_3`

D

`CH_3 - underset(CH_3) underset(|)C=underset(CH_3 ) underset(|)C-CH_3`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem, we will analyze the reaction of the given compound with HNO2 step by step. ### Step 1: Identify the Reactants The reactant is a compound with both an alcohol (OH) and an amino group (NH2). The structure can be represented as: \[ CH_3 - C(OH)(NH_2) - C(CH_3)(CH_3) \] ### Step 2: Reaction with HNO2 When HNO2 (Nitrous acid) is introduced, it reacts with the amino group (NH2). This reaction is characteristic of primary amines, leading to the formation of a diazonium ion. ### Step 3: Mechanism of Reaction 1. **Formation of Diazonium Ion**: - The NH2 group reacts with HNO2, which can be represented as HONO. - The nitrogen in NH2 acts as a nucleophile and attacks the electrophilic nitrous acid, leading to the formation of a diazonium ion. 2. **Formation of Carbocation**: - The diazonium ion is unstable due to the presence of alkyl groups, which leads to the loss of nitrogen gas (N2) and the formation of a carbocation. ### Step 4: Rearrangement of Carbocation - The carbocation formed is subject to rearrangement to form a more stable carbocation. In this case, a methyl shift occurs, where a methyl group from one carbon moves to the adjacent carbon, stabilizing the positive charge. ### Step 5: Nucleophilic Attack by Water - Water, acting as a nucleophile, attacks the carbocation, leading to the formation of a geminal diol (a compound with two hydroxyl groups on the same carbon). ### Step 6: Dehydration to Form Ketone - The geminal diol is unstable and can lose a molecule of water, resulting in the formation of a ketone. ### Final Product The final product after the reaction with HNO2 and subsequent rearrangements and dehydration is: \[ CH_3 - C(=O) - C(CH_3)(CH_3) \] This is a ketone. ### Conclusion The correct answer for the product of the reaction is a ketone derived from the original compound. ---
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