4) Using your resonance structures from the previous question, classify each substituent as $\pi$ electron-donating or $\pi$-electron-withdrawing with respect to the aromatic ring. Using your knowledge (or a table) of electronegativities, predict whether each group is $\sigma$-electrondonating or $\sigma$-electron-withdrawing with respect to the aromatic ring. Complete the table below. ( 6 pts)
\begin{tabular}{ccc}
Molecule & $\sigma$-electron effect & $\pi$-electron effect \
\hline Aniline & & \
Styrene & &
\end{tabular}

Benzoic Acid
10

Question

4) Using your resonance structures from the previous question, classify each substituent as $\pi$ electron-donating or $\pi$-electron-withdrawing with respect to the aromatic ring. Using your knowledge (or a table) of electronegativities, predict whether each group is $\sigma$-electrondonating or $\sigma$-electron-withdrawing with respect to the aromatic ring. Complete the table below. ( 6 pts)
\begin{tabular}{ccc} 
Molecule & $\sigma$-electron effect & $\pi$-electron effect \
\hline Aniline & & \
Styrene & &
\end{tabular}

Benzoic Acid
10

Accepted Answer

∻Solution∻ ‖ 1 ⋮ **Identify the substituents**: The molecules listed are Aniline, Styrene, and Benzoic Acid. We need to classify each substituent as $\pi$ electron-donating or $\pi$-electron-withdrawing and $\sigma$-electron-donating or $\sigma$-electron-withdrawing. ‖ ‖ 2 ⋮ **Analyze Aniline**: Aniline has an amino group ($-NH_2$) attached to the benzene ring. The amino group is an electron-donating group due to its lone pair of electrons, which can participate in resonance with the aromatic ring. Therefore, it is $\pi$ electron-donating. The amino group is also $\sigma$-electron-donating because nitrogen is less electronegative than carbon, and it donates electron density through the sigma bond. ‖ ‖ 3 ⋮ **Analyze Styrene**: Styrene has a vinyl group ($-CH=CH_2$) attached to the benzene ring. The vinyl group is $\pi$ electron-donating because the double bond can participate in resonance with the aromatic ring. However, it is $\sigma$-electron-withdrawing because the sp2 hybridized carbon of the vinyl group is more electronegative than the sp3 hybridized carbon of the benzene ring. ‖ ‖ 4 ⋮ **Analyze Benzoic Acid**: Benzoic Acid has a carboxyl group ($-COOH$) attached to the benzene ring. The carboxyl group is $\pi$-electron-withdrawing because the carbonyl group ($C=O$) pulls electron density away from the aromatic ring through resonance. It is also $\sigma$-electron-withdrawing because the carbonyl carbon is more electronegative than the benzene carbon, pulling electron density through the sigma bond. ‖ ∻Answer∻ ⚹ - Aniline: $\sigma$-electron donating, $\pi$-electron donating - Styrene: $\sigma$-electron withdrawing, $\pi$-electron donating - Benzoic Acid: $\sigma$-electron withdrawing, $\pi$-electron withdrawing ⚹ ∻Key Concept∻ ⚹ The electron-donating or withdrawing nature of substituents affects the electron density of the aromatic ring through resonance ($\pi$) and inductive ($\sigma$) effects. ⚹ ∻Explanation∻ ⚹ Substituents can either donate or withdraw electron density from the aromatic ring, influencing its reactivity and stability. The $\pi$-electron effect involves resonance, while the $\sigma$-electron effect involves the inductive effect based on electronegativity. ⚹◊What are the key factors that determine whether a substituent is $\pi$-electron-donating or $\pi$-electron-withdrawing with respect to an aromatic ring in organic chemistry⍭ Generate me a similar question◊

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