Ch. 2 - General Chemistry Translated: Finding the Electrons

Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition

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Mullins 1st Edition

Ch. 2 - General Chemistry Translated: Finding the Electrons

Problem 48a

Chapter 1, Problem 48a

Draw the resonance structure that would result from the indicated movement of electrons.
(a)

Verified step by step guidance

Identify the starting structure and locate the electrons that are indicated to move. These could be lone pairs, π-bonds, or negative charges. Ensure you understand the direction of the arrow (from electron source to destination).

Determine the type of resonance movement indicated. Common types include: (1) lone pair to π-bond, (2) π-bond to lone pair, or (3) π-bond to π-bond. This will help you predict the new bonding arrangement.

Redraw the structure, showing the new position of the electrons after the indicated movement. Adjust the formal charges on atoms as necessary to reflect the redistribution of electrons.

Verify that the new structure follows the rules of resonance: (1) the total number of electrons remains the same, (2) the octet rule is satisfied for second-row elements, and (3) the overall charge of the molecule or ion is conserved.

Check for additional resonance structures by repeating the process for other possible electron movements, if applicable. This will help you identify all significant resonance contributors.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Resonance Structures

Resonance structures are different ways of drawing the same molecule that illustrate the delocalization of electrons. They are used to represent molecules where the electron distribution cannot be depicted by a single Lewis structure. Each resonance structure contributes to the overall hybrid structure, which is more stable than any individual form.

Electron Movement

Electron movement in organic chemistry typically refers to the shifting of electron pairs during chemical reactions or when drawing resonance structures. This movement is often depicted using arrows, where a double-headed arrow indicates the movement of a pair of electrons, while a single-headed arrow shows the movement of a single electron. Understanding how electrons can move helps in predicting the stability and reactivity of molecules.

Stability of Resonance Structures

The stability of resonance structures is determined by factors such as the octet rule, charge distribution, and the presence of formal charges. More stable resonance structures have full octets for all atoms, minimal formal charges, and negative charges on more electronegative atoms. Evaluating the stability of these structures is crucial for predicting the behavior of molecules in chemical reactions.

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Drawing Resonance Structures

Related Practice

Textbook Question

i) Which of the following resonance structures represents the 'actual' structure of the molecule shown? (ii) Which contributes more to the resonance hybrid? (iii) Why?

(a)

(b)

(c)

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Textbook Question

Each pair of structures represents two valid resonance structures. Use the arrow-pushing formalism to justify the formation of the one on the left from the one on the right.

(b)

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Textbook Question

To which atom of formaldehyde would you expect H⁺ to add?

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Textbook Question

How might electrons be excited from π to π* based on the molecular orbital diagram shown? [This will be relevant in Chapter 21.]

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Textbook Question

Each pair of structures represents two valid resonance structures. Use the arrow-pushing formalism to justify the formation of the one on the left from the one on the right.

(a)

1244

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Textbook Question

For each of the molecules shown, do the following:

(i) Identify all pushable pairs.

(ii) Identify all places where electrons can be pushed.

(iii) Draw one valid resonance structure.

(a)

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