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R-NH2 is the main product of reactio...

`R-NH_2 ` is the main product of reaction of` RCONH_2 ` and `[Br_2+ KOH ].` In this reaction intermediates are :
`(a ) RCONHBr (b ) RNHBr `
`(c ) R-N=C=O " " (d ) RCONBr_2`
Correct answer is :

A

a,b

B

a,c

C

c,d

D

b,c,d

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem regarding the reaction of RCONH2 with Br2 and KOH, we will analyze the mechanism of the Hofmann Bromamide reaction step by step. ### Step 1: Understanding the Reactants The reactant in this case is an amide, RCONH2. When it reacts with bromine (Br2) in the presence of a strong base like KOH, we need to identify the intermediates that form during this reaction. **Hint:** Identify the functional groups present in the reactants and their reactivity. ### Step 2: Base Abstraction In the first step of the reaction, the strong base (KOH) abstracts one of the acidic hydrogens from the amide. This results in the formation of a negatively charged nitrogen species, which can be represented as R-C(=O)-NH-. **Hint:** Look for the acidic hydrogen in the amide that can be removed by the base. ### Step 3: Formation of Bromamide The negatively charged nitrogen acts as a nucleophile and attacks the bromine molecule (Br2). This leads to the formation of an intermediate bromamide, R-C(=O)-NH-Br. **Hint:** Consider how nucleophiles interact with electrophiles in organic reactions. ### Step 4: Further Base Abstraction Another molecule of the base (KOH) abstracts the remaining acidic hydrogen from the bromamide intermediate. This results in the formation of R-C(=O)-Br, with the bromine now being part of the carbonyl compound. **Hint:** Identify the role of the base in facilitating the removal of protons in the reaction. ### Step 5: Formation of Isocyanate The bromine atom is released, leading to the formation of a nitrene intermediate. This nitrene can rearrange to form an isocyanate, R-N=C=O. **Hint:** Understand the rearrangement processes that can occur with intermediates in organic reactions. ### Step 6: Hydrolysis of Isocyanate The isocyanate (R-N=C=O) undergoes hydrolysis in the presence of water, resulting in the formation of the final product, which is an amine (RNH2) and carbon dioxide (CO2). **Hint:** Consider the role of water in converting isocyanate into a more stable product. ### Conclusion: Identifying the Intermediates From the steps outlined, we can identify the intermediates formed during the reaction: 1. R-C(=O)-NH-Br (bromamide) 2. R-N=C=O (isocyanate) Thus, the correct intermediates from the options provided are: - (a) RCONHBr - (c) R-N=C=O ### Final Answer: The correct intermediates are (a) RCONHBr and (c) R-N=C=O.
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