CHAPTER 2: CHEMICAL EFFECTS

The content includes:

2.1. Electronic effects

2.1.1. Inductive effect

2.1.2. Resonance effect

2.1.3. Hyperconjugation effect

2.2. Prediction of the relative strengths of common organic

acids and bases

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 CHAPTER 2: CHEMICAL EFFECTS

2.1.Electronic effects

2.1.1 Inductive effect

Polarization of -bond due to electron-withdrawing or

electron-donating effect of adjacent groups or atoms

Type of inductive effect

- Negative inductive effect (-I)

- Positive inductive effect (+I)

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- Negative inductive effect (-I): electron withdrawing groups

An electronegative atom attach to the molecular

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Electronegativity Values

H C N O F
2.1 2.5 3.0 3.5 4.0
Si P S Cl
1.8 2.1 2.4 3.0
Br
2.8
I
2.5
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+I: electron donating group

An atom of small electronegativity is attach to the molecular

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2.1.2. Resonant effect

The electron withdrawing or donating effect was

attributed to a substituent through delocalization of p or n
electrons

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Type of resonance effect

- Negative resonance effect (-C): groups withdraw

electron by delocalization mechanism

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Positive resonance effect (+C): groups release electrons

to the rest of molecular by delocalization

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2.1.3. Hyperconjugation effect

The delocalization of -electrons into adjacent pi-orbital

is called hyperconjugation

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2.2 Prediction of the relative strengths of common organic

acids and bases
Rank in order of increasing acidity

1)

2)

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3)

4)

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