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The correct reactivity order with the nu...

The correct reactivity order with the nucleophile is :

A

`CH_(3)COClgtCH_(3)CONH_(2)gtCH_(3)COOCH_(3)`

B

`CH_(3)COClgtCH_(3)COOCH_(3)gtCH_(3)COONH_(2)`

C

`CH_(3)CONH_(2)gtCH_(3)COOCH_(3)gtCH_(3)COCl`

D

`CH_(3)COOCH_(3)gtCH_(3)COClgtCH_(3)CONH_(2)`

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AI Generated Solution

The correct Answer is:
To determine the correct reactivity order of nucleophiles with carbonyl compounds, we need to analyze the influence of different substituents on the carbonyl carbon. Here’s a step-by-step breakdown of the reasoning: ### Step 1: Identify the Carbonyl Compounds We are considering three carbonyl compounds: 1. CH3C(=O)Cl (Carbonyl chloride) 2. CH3C(=O)NH2 (Amide) 3. CH3C(=O)OCH3 (Ester) ### Step 2: Analyze the Effect of Substituents - **Carbonyl Chloride (CH3C(=O)Cl)**: The chlorine atom is a good leaving group and exhibits a -I (inductive) effect, which increases the positive character of the carbonyl carbon. This makes it more susceptible to nucleophilic attack. - **Amide (CH3C(=O)NH2)**: The amine group (NH2) is a +R (resonance) donor, which means it can donate electron density to the carbonyl carbon, reducing its positive character and making it less reactive compared to carbonyl chloride. - **Ester (CH3C(=O)OCH3)**: The methoxy group (OCH3) also acts as a +R donor, similar to the amine group. However, oxygen is more electronegative than nitrogen, which means it holds onto its electrons more tightly. This results in a greater reduction of the positive character of the carbonyl carbon compared to the amide. ### Step 3: Determine the Reactivity Order Based on the analysis: - **Carbonyl Chloride (CH3C(=O)Cl)** is the most reactive due to the presence of a good leaving group (Cl) and the strong +I effect. - **Amide (CH3C(=O)NH2)** is next, as it has a +R effect but is less reactive than carbonyl chloride. - **Ester (CH3C(=O)OCH3)** is the least reactive due to the strong +R effect from the methoxy group, which stabilizes the carbonyl carbon. Thus, the correct reactivity order with respect to nucleophiles is: **Cl > NH2 > OCH3** ### Final Answer The correct reactivity order with the nucleophile is: **Cl > NH2 > OCH3** (Option A). ---
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ALLEN-ALKENE, ALKANE & ALKYNE -EXCERSISE-1
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