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Ch.1 - Structure and Bonding
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh.1 - Structure and BondingProblem 26b,c
Chapter 1, Problem 26b,c

b. Draw the resonance forms for ozone (bonded O–O–O)
c. Sulfur dioxide has one more resonance form than ozone. Explain why this structure is not possible for ozone.

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1
To draw the resonance forms for ozone (O₃), start by considering the Lewis structure. Ozone consists of three oxygen atoms in a bent shape. The central oxygen atom is bonded to the other two oxygen atoms.
In the first resonance form, draw a double bond between the central oxygen and one of the terminal oxygens, and a single bond between the central oxygen and the other terminal oxygen. Assign formal charges: the oxygen with the double bond has a formal charge of 0, the central oxygen has a formal charge of +1, and the oxygen with the single bond has a formal charge of -1.
In the second resonance form, move the double bond to the other terminal oxygen. This means the double bond is now between the central oxygen and the other terminal oxygen. Reassign the formal charges: the oxygen with the double bond has a formal charge of 0, the central oxygen has a formal charge of +1, and the other terminal oxygen has a formal charge of -1.
For sulfur dioxide (SO₂), it has one more resonance form than ozone because sulfur can expand its octet, allowing for additional resonance structures. In SO₂, sulfur can form a double bond with each oxygen atom, resulting in three resonance forms: one with a double bond to one oxygen, one with a double bond to the other oxygen, and one with double bonds to both oxygens.
Ozone cannot have a resonance form with double bonds to both terminal oxygens because oxygen cannot expand its octet like sulfur can. Oxygen is limited to an octet configuration, which restricts the number of resonance forms compared to sulfur dioxide.

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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 Lewis structures for a molecule that depict the same arrangement of atoms but differ in the placement of electrons. They help illustrate the delocalization of electrons within a molecule, which can stabilize the molecule. Understanding resonance is crucial for predicting molecular behavior and properties.
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Ozone Molecular Structure

Ozone (O3) consists of three oxygen atoms bonded in a linear arrangement. The molecule exhibits resonance, with electrons delocalized across the O-O-O bonds. This delocalization results in partial charges and bond lengths that differ from those predicted by a single Lewis structure, making resonance forms essential for accurate representation.
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Sulfur Dioxide Resonance

Sulfur dioxide (SO2) has a bent molecular geometry and exhibits resonance with more possible structures than ozone due to the presence of sulfur, which can expand its octet. This allows for additional resonance forms, contributing to the molecule's stability. The difference in resonance forms between SO2 and O3 is due to sulfur's ability to accommodate more electrons than oxygen.
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Related Practice
Textbook Question

Give the relationship between the following pairs of structures. The possible relationships are:

same compound

constitutional isomers (structural isomers)

cis-trans isomers

not isomers (different molecular formula)


(g) CH3–CH2–CH2–CH3 and CH3–CH=CH–CH3

(h) CH2=CH–CH2CH2CH3 and CH3–CH=CH–CH2CH3

(i) CH2=CHCH2CH2CH3 and CH3CH2CH2CH=CH2

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Textbook Question

a. Draw the resonance forms for SO2 (bonded O–S–O).

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Textbook Question

There is a small portion of the periodic table that you must know to do organic chemistry. Construct this part from ­memory, using the following steps.

a. From memory, make a list of the elements in the first two rows of the periodic table, together with their numbers of valence electrons

b. Use this list to construct the first two rows of the periodic table.

c. Organic compounds often contain sulfur, phosphorus, chlorine, bromine, and iodine. Add these elements to your ­periodic table.

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Textbook Question

Name the element that corresponds to each electronic configuration.

a. 1s2 2s2 2p2

b. 1s2 2s2 2p4

c. 1s2 2s2 2p6 3s2 3p3

d. 1s2 2s2 2p6 3s2 3p5

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Textbook Question

For each compound, state whether its bonding is covalent, ionic, or a mixture of covalent and ionic.

a. NaCl

b. NaOH

c. CH3Li

d. CH2Cl2

e. NaOCH3

f. HCO2Na

g. CF4

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Textbook Question

Give the relationship between the following pairs of structures. The possible relationships are:

same compound

constitutional isomers (structural isomers)

cis-trans isomers

not isomers (different molecular formula)


(j)

(k)

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