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Ph -N =C=O overset((i)CH3MgBr)underset(...

`Ph -N =C=O overset((i)CH_3MgBr)underset((ii)H_2O)rarrPoverset(LiAlH_4)rarrQ`

A

P is `PhN=overset(CH_3)overset(|)C-OH` and Q is `PH-NH-CH_3`

B

P is Ph - NH `-CH_3` and Q is `overset("**")NH_3`

C

P is `Ph-NH-underset(O)underset(||)C-CH_3and Q` is `Ph-NH-CH_2-CH_3`

D

P is `Ph-NH-underset(OH)underset(|)(CH)-CH_3and Q` is `Ph-NH-underset(CH_3)underset(|)(CH)-CH_3`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the given reaction sequence, we will identify the products P and Q step by step. ### Step 1: Identify the starting compound The starting compound is phenyl isocyanate, which can be represented as: \[ \text{Ph-N} = \text{C} = \text{O} \] ### Step 2: Reaction with Grignard Reagent The first step involves the reaction of phenyl isocyanate with methylmagnesium bromide (CH₃MgBr). In this reaction, the nucleophilic carbon (C) of the Grignard reagent attacks the electrophilic carbon of the isocyanate group. 1. The nucleophile (CH₃⁻) attacks the carbon atom of the isocyanate (C=O). 2. This results in the formation of a tetrahedral intermediate with a negatively charged oxygen. The reaction can be represented as: \[ \text{Ph-N} = \text{C} = \text{O} + \text{CH}_3\text{MgBr} \rightarrow \text{Ph-N}(\text{C}(\text{CH}_3)O^{-})\text{MgBr}^{+} \] ### Step 3: Hydrolysis Next, we perform hydrolysis on the intermediate formed in the previous step. Hydrolysis will convert the alkoxide into an alcohol. 1. The alkoxide (O⁻) will be protonated by water (H₂O). 2. The Grignard reagent (MgBr) will be eliminated, leading to the formation of an alcohol. The product after hydrolysis (P) will be: \[ \text{Ph-N}(\text{C}(\text{CH}_3)OH) \] ### Step 4: Tautomerism The product P can undergo tautomerism. In this case, the nitrogen can accept a hydrogen atom from the hydroxyl group, leading to a shift of the double bond. The tautomeric form of P will be: \[ \text{Ph-NH-C}(\text{CH}_3)=\text{OH} \] ### Step 5: Reduction with Lithium Aluminium Hydride Now, we treat the product P with lithium aluminium hydride (LiAlH₄), which is a strong reducing agent. 1. The carbonyl group (C=O) in the tautomer will be reduced to a methylene group (C-H). 2. The nitrogen will remain attached to the carbon. The final product Q will be: \[ \text{Ph-NH-CH}_2\text{C}(\text{CH}_3) \] ### Summary of Products - Product P: \[ \text{Ph-NH-C}(\text{CH}_3)=\text{OH} \] - Product Q: \[ \text{Ph-NH-CH}_2\text{C}(\text{CH}_3) \]
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