QuestionJune 27, 2025

Which of the following compounds is the most reactive dienophile in a Diels-Alder reaction with 1,3 -butadiene? (CH_(3))_(2)C=CH_(2) CH_(2)=CHOH CH_(2)=CH_(2) CH_(3)CH=CHCOOH CH_(2)=CHOCH_(3)

Which of the following compounds is the most reactive dienophile in a Diels-Alder reaction with 1,3 -butadiene? (CH_(3))_(2)C=CH_(2) CH_(2)=CHOH CH_(2)=CH_(2) CH_(3)CH=CHCOOH CH_(2)=CHOCH_(3)
Which of the following compounds is the most reactive dienophile in a Diels-Alder reaction with 1,3 -butadiene?
(CH_(3))_(2)C=CH_(2)
CH_(2)=CHOH
CH_(2)=CH_(2)
CH_(3)CH=CHCOOH
CH_(2)=CHOCH_(3)

Solution
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Answer

\( \mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCOOH} \) Explanation 1. Identify Electron-Withdrawing Groups The reactivity of a dienophile in a Diels-Alder reaction increases with the presence of electron-withdrawing groups. Analyze each compound for such groups. 2. Evaluate Each Compound 1. \( (\mathrm{CH}_{3})_{2} \mathrm{C}=\mathrm{CH}_{2} \): No electron-withdrawing groups. 2. \( \mathrm{CH}_{2}=\mathrm{CHOH} \): Hydroxyl group is not strongly electron-withdrawing. 3. \( \mathrm{CH}_{2}=\mathrm{CH}_{2} \): No electron-withdrawing groups. 4. \( \mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCOOH} \): Carboxylic acid group is electron-withdrawing. 5. \( \mathrm{CH}_{2}=\mathrm{CHOCH}_{3} \): Ether group is not strongly electron-withdrawing. 3. Determine Most Reactive Dienophile The compound with the strongest electron-withdrawing group will be the most reactive. Here, \( \mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCOOH} \) has a carboxylic acid group, making it the most reactive.

Explanation

1. Identify Electron-Withdrawing Groups<br /> The reactivity of a dienophile in a Diels-Alder reaction increases with the presence of electron-withdrawing groups. Analyze each compound for such groups.<br /><br />2. Evaluate Each Compound<br /> 1. \( (\mathrm{CH}_{3})_{2} \mathrm{C}=\mathrm{CH}_{2} \): No electron-withdrawing groups.<br /> 2. \( \mathrm{CH}_{2}=\mathrm{CHOH} \): Hydroxyl group is not strongly electron-withdrawing.<br /> 3. \( \mathrm{CH}_{2}=\mathrm{CH}_{2} \): No electron-withdrawing groups.<br /> 4. \( \mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCOOH} \): Carboxylic acid group is electron-withdrawing.<br /> 5. \( \mathrm{CH}_{2}=\mathrm{CHOCH}_{3} \): Ether group is not strongly electron-withdrawing.<br /><br />3. Determine Most Reactive Dienophile<br /> The compound with the strongest electron-withdrawing group will be the most reactive. Here, \( \mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCOOH} \) has a carboxylic acid group, making it the most reactive.
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