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Predict the nature of P in the following...

Predict the nature of P in the following reaction : `Me_(3)"CCH"_2 NH_2 overset("HONO") (to) P("main product")`

A

`Me_(3)"CCH"_(2) OH`

B

`Me_(2)"CCH" = CH_(2)`

C

`Me_(2) CO(OH)C_(2) H_(5)`

D

`Me_(3)"CCH"_(2) NH(NO)`

Text Solution

AI Generated Solution

The correct Answer is:
To predict the nature of P in the reaction of Me₃CCH₂NH₂ with HONO, we can follow these steps: ### Step 1: Identify the Reactants The reactant is Me₃CCH₂NH₂, which is a tertiary amine. The structure can be drawn as follows: - The central carbon (C) is bonded to three methyl groups (Me) and one CH₂NH₂ group. ### Step 2: Understand the Role of HONO HONO (nitrous acid) can decompose to produce nitrosonium ion (NO⁺), which acts as an electrophile. This electrophile will attack the nitrogen atom in the amine group. ### Step 3: Electrophilic Attack The nitrosonium ion (NO⁺) will attack the nitrogen atom of the amine (NH₂) group. This results in the formation of a positively charged intermediate: - The nitrogen atom will have four bonds (three to hydrogen and one to the nitrosonium ion), resulting in a positive charge on nitrogen. ### Step 4: Formation of Carbocation As the reaction proceeds, the bond between the nitrogen and the carbon (C) will break, leading to the formation of a carbocation: - The carbocation will be formed on the carbon adjacent to the nitrogen, which is a secondary carbocation. ### Step 5: Methyl Shift The secondary carbocation is not very stable, so a 1,2-methyl shift occurs. This means that one of the methyl groups from the carbon adjacent to the carbocation will shift to stabilize the carbocation: - The structure now has a more stable tertiary carbocation. ### Step 6: Nucleophilic Attack by Water Water can then attack the carbocation, leading to the formation of an alcohol: - The final product will have an OH group replacing the NH₂ group. ### Step 7: Final Product Structure The final product P can be represented as: - Me₂C(OH)CH₂CH₃, which is a tertiary alcohol. ### Conclusion The nature of P is a tertiary alcohol resulting from the reaction of Me₃CCH₂NH₂ with HONO. ---

To predict the nature of P in the reaction of Me₃CCH₂NH₂ with HONO, we can follow these steps: ### Step 1: Identify the Reactants The reactant is Me₃CCH₂NH₂, which is a tertiary amine. The structure can be drawn as follows: - The central carbon (C) is bonded to three methyl groups (Me) and one CH₂NH₂ group. ### Step 2: Understand the Role of HONO HONO (nitrous acid) can decompose to produce nitrosonium ion (NO⁺), which acts as an electrophile. This electrophile will attack the nitrogen atom in the amine group. ...
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