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Ch.1 - Structure and Bonding
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728당신이 사용하는 게 아니라요?교과서 변경
1장, 문제 42j,k

Draw the important resonance forms to show the delocalization of charges in the following ions. In each case, indicate the major resonance form(s).
(j)
(k)

검증된 단계별 안내
1
Identify the conjugated system in each ion. For ion j, [CH3CH=CHCH=CHCH2CH2]+, the conjugated system involves the alternating single and double bonds starting from the second carbon. For ion k, [CH2CH=CHOCH=CH2]+, the conjugated system involves the alternating single and double bonds starting from the first carbon.
For ion j, draw the initial structure with the positive charge on the terminal carbon (CH2). Then, move the pi electrons from the double bond between the second and third carbon to form a new double bond between the first and second carbon, shifting the positive charge to the third carbon.
Continue the resonance for ion j by moving the pi electrons from the double bond between the fourth and fifth carbon to form a new double bond between the third and fourth carbon, shifting the positive charge to the fifth carbon. Repeat this process to explore all possible resonance structures.
For ion k, start with the initial structure where the positive charge is on the oxygen atom. Move the pi electrons from the double bond between the first and second carbon to form a new double bond between the oxygen and the second carbon, shifting the positive charge to the first carbon.
Continue the resonance for ion k by moving the pi electrons from the double bond between the fourth and fifth carbon to form a new double bond between the third and fourth carbon, shifting the positive charge to the fifth carbon. Explore all possible resonance structures and identify the major resonance form based on the stability of the structures (e.g., full octets, charge distribution).

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영상 길이:
8m

주요 개념

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Resonance Structures

Resonance structures are different Lewis structures for a molecule that depict the same arrangement of atoms but differ in the distribution of electrons. They are used to represent delocalized electrons within certain molecules or polyatomic ions where the bonding cannot be expressed by a single Lewis structure. The true structure is a hybrid of all possible resonance forms.
추천 영상:
03:04
Drawing Resonance Structures

Delocalization of Charges

Delocalization of charges refers to the distribution of electron density across multiple atoms, which can stabilize ions or molecules. In resonance, this involves the movement of electrons, typically pi electrons or lone pairs, across adjacent atoms, reducing the energy of the system. This concept is crucial for understanding the stability and reactivity of organic ions.
추천 영상:
01:34
Calculating formal and net charge.

Major and Minor Resonance Forms

In resonance, not all structures contribute equally to the resonance hybrid. Major resonance forms are those that are more stable, typically having full octets on atoms, minimal formal charges, and negative charges on more electronegative atoms. Minor forms are less stable and contribute less to the overall hybrid. Identifying these helps predict the most likely structure and properties of the ion.
추천 영상:
03:04
Drawing Resonance Structures