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Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711Non è quello che usi tu?Cambia libro di testo
Tutti i libri di testoBruice 8th EditionCh. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of BenzeneProblema 61g,h,i
Capitolo 8, Problema 61g,h,i

Which of the following has delocalized electrons?
g. Chemical structure showing delocalized electrons with a positive charge on a carbon atom connected to a double bond.
h. Chemical structure of a hydrocarbon with alternating double bonds, indicating potential resonance structures.
i. Chemical structure of a compound with delocalized electrons, labeled with molecular formula CH3CH2NHCH2CH=CHCH3.

Guida verificata passo dopo passo
1
Step 1: Understand the concept of delocalized electrons. Delocalized electrons are electrons that are not confined to a single atom or bond but are spread across multiple atoms, typically in conjugated systems or resonance structures.
Step 2: Analyze structure (a). Structure (a) contains alternating double bonds (a conjugated system) and a positively charged carbon atom. The conjugated system allows for delocalization of π-electrons across the double bonds.
Step 3: Analyze structure (b). Structure (b) has a positively charged carbon atom, but the double bonds are not conjugated (they are separated by a single bond). This lack of conjugation prevents delocalization of electrons.
Step 4: Analyze structure (c). Structure (c) contains a nitrogen atom with a lone pair and a double bond nearby. However, the lone pair on nitrogen is not part of a conjugated system, and the double bond does not interact with the lone pair to create delocalization.
Step 5: Conclude that structure (a) has delocalized electrons due to the conjugated system, while structures (b) and (c) do not exhibit delocalization of electrons.

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Delocalized Electrons

Delocalized electrons are electrons that are not associated with a single atom or a single bond but are spread over several atoms. This phenomenon occurs in molecules with conjugated systems or resonance structures, where electrons can move freely between multiple bonding sites, contributing to the stability and reactivity of the molecule.
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Resonance Structures

Resonance structures are different ways of drawing the same molecule that illustrate the delocalization of electrons. These structures help chemists understand the actual electron distribution in a molecule, which is often a hybrid of the resonance forms. The true structure is a blend of these forms, leading to increased stability.
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Conjugation

Conjugation refers to the overlap of p-orbitals across adjacent double or triple bonds, allowing for the delocalization of electrons. This arrangement stabilizes the molecule and can affect its reactivity and color. Conjugated systems are often found in organic compounds, such as dyes and pigments, where they contribute to unique properties.
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Conjugated states
Pratica correlata
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Refer to the electrostatic potential maps <IMAGE> to answer the following questions:

c. Why is the center of the electrostatic potential map of benzene more red than the center of the electrostatic potential map of pyridine?

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Which of the following compounds could be protonated without destroying its aromaticity?

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a. Draw resonance contributors for the following species, showing all the lone pairs:

b. For each species, indicate the most stable resonance contributor.

3. NO2-

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Draw resonance contributors for the following ions:

a.

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Which of the following has delocalized electrons?

j.

k.

l.

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Which of the following has delocalized electrons?

a.

b.

c.

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