11. Bonding & Molecular Structure

Resonance Structures

11. Bonding & Molecular Structure

Resonance Structures

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Resonance Structures Example 1

Jules Bruno

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02:19

Resonance Structures Example 2

Jules Bruno

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07:36

Resonance & Bond Order

Eileen Sullivan

05:12

Resonance Structures of N2O (dinitrogen monoxide, nitrous oxide)

chemistNATE

08:58

Resonance | General Chemistry II | 1.6

Professor Derricotte

05:32

Resonance Structures of NO3(-1), nitrate ion

chemistNATE

04:32

CHEMISTRY 101 - Drawing Lewis Structures: Resonance, nitrate

Matthew Gerner

10:31

Resonance Structures, Basic Introduction - How To Draw The Resonance Hybrid, Chemistry

The Organic Chemistry Tutor

04:09

Drawing Lewis Structures: Resonance Structures - Chemistry Tutorial

TheChemistrySolution

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Practice this topic

Open Question

Draw all possible resonance structures for the chlorate ion, ClO₃^–?

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Multiple Choice

Determine the average charge of the oxygen atoms within the chlorite ion, ClO₂^–.

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Multiple Choice

Determine which of the following drawings would be the best structure for the N₂O molecule.

a) a

b) b

c) c

d) All are equally stable

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Multiple Choice

Which of the following phosphate, PO₄^3- Lewis structures is the best, most valid resonance structure?

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Open Question

Draw all the resonance structures for the following ionic compound:RbIO₂

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Multiple Choice

Which of the following substances exhibits resonance?

Multiple Choice

The Lewis structure that is likely to contribute the most to the overall structure of NCS⁻ should have:

Textbook Question

Which of the following pairs represent resonance structures? (LO 7.13) (a)

(b)

(c)

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Textbook Question

The structure for the DNA base cytosine is shown.

Which of the following is not a resonance structure of cytosine? (LO 7.13) (a)

(b)

(c)

(d)

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Textbook Question

Use formal charge to select which resonance structure makes the largest contribution to the resonance hybrid. (LO 7.16) (a) Structure I (b) Structure II (c) Structure III (d) All structures are equivalent and make the same contri-bution to the resonance hybrid. (I)

(II)

(III)

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Textbook Question

Draw Lewis structures for the following: (f) NO3-.

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Textbook Question

For each of the following molecules or ions of sulfur and oxygen, write a single Lewis structure that obeys the octet rule, and calculate the oxidation numbers and formal charges on all the atoms: (c) SO32- Write a single Lewis structure that obeys the octet rule for SO3 2 - and assign the formal charges on all the atoms.

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Textbook Question

Consider the formate ion, HCO2-, which is the anion formed when formic acid loses an H+ ion. The H and the two O atoms are bonded to the central C atom. (b) Are resonance structures needed to describe the structure?

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Textbook Question

Using only the elements P, Br, and Mg, give formulas for the following. (b) A molecular compound with polar covalent bonds that obeys the octet rule and has no formal charges

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Textbook Question

Mothballs are composed of naphthalene, C10H8, a molecule that consists of two six-membered rings of carbon fused along an edge, as shown in this incomplete Lewis structure:

(b) Do you expect the C¬C bond lengths in the molecule to be similar to those of C¬C single bonds, C'C double bonds, or intermediate between C¬C single and C'C double bonds?

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Textbook Question

Mothballs are composed of naphthalene, C10H8, a molecule that consists of two six-membered rings of carbon fused along an edge, as shown in this incomplete Lewis structure:

(a) Draw all of the resonance structures of naphthalene. How many are there?

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Textbook Question

Using only the elements Ca, Cl, and Si, give formulas for the following. (b) A molecular compound with polar covalent bonds that obeys the octet rule and has no formal charges

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Textbook Question

Write a Lewis structure that obeys the octet rule for each molecule or ion. Include resonance structures if necessary and assign formal charges to each atom. a. SeO2

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Textbook Question

Write a Lewis structure that obeys the octet rule for each ion. Include resonance structures if necessary and assign formal charges to each atom. a. ClO3- b. ClO4- c. NO3- d. NH4+

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Textbook Question

In the sulphate ion, SO42-, the sulphur atom is the central atom with the other 4 oxygen atoms attached to it. (d) How many electrons are in the p system of the ion?

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Textbook Question

In the sulphate ion, SO42-, the sulphur atom is the central atom with the other 4 oxygen atoms attached to it. (c) Are there multiple equivalent resonance structures for the ion?

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Textbook Question

(a) Describe the molecule xenon trioxide, XeO3, using four possible Lewis structures, one each with zero, one, two, or three Xe¬O double bonds. (b) Do any of these resonance structures satisfy the octet rule for every atom in the molecule? (c) Do any of the four Lewis structures have multiple resonance structures? If so, how many resonance structures do you find? (d) Which of the Lewis structures in part (a) yields the most favorable formal charges for the molecule?

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Textbook Question

There are many Lewis structures you could draw for sulfuric acid, H2SO4 (each H is bonded to an O). (b) What Lewis structure(s) would you draw to minimize formal charge?

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Textbook Question

How important is the resonance structure shown here to the overall structure of carbon dioxide? Explain.

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Textbook Question

The hypochlorite ion, ClO-, acts as a weak base. (b) When ClO- acts as a base, which atom, Cl or O, acts as the proton acceptor? (c) Can you use formal charges to rationalize your answer to part (b)?

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Textbook Question

Some chemists believe that satisfaction of the octet rule should be the top criterion for choosing the dominant Lewis structure of a molecule or ion. Other chemists believe that achieving the best formal charges should be the top criterion. Consider the dihydrogen phosphate ion, H2PO4-, in which the H atoms are bonded to O atoms. (b) What is the predicted dominant Lewis structure if achieving the best formal charges is the top criterion?

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Textbook Question

Draw the Lewis structure (including resonance structures) for the acetate ion (CH3COO- ). For each resonance structure, assign formal charges to all atoms that have formal charge.

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Textbook Question

Draw the Lewis structure (including resonance structures) for methyl azide (CH3N3). For each resonance structure, assign formal charges to all atoms that have formal charge.

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Textbook Question

Draw as many resonance structures as you can for the following nitrogen-containing compounds. Not all will obey the octet rule. Use curved arrows to depict the conversion of one structure into another. (d) N2O31ONNO22

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Textbook Question

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Textbook Question

Which of the following pairs of structures represent resonance forms, and which do not? (a)

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Textbook Question

Each compound contains both ionic and covalent bonds. Write ionic Lewis structures for each, including the covalent structure for the ion in brackets. Write resonance structures if necessary. c. KNO3

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Textbook Question

Each compound contains both ionic and covalent bonds. Write ionic Lewis structures for each, including the covalent structure for the ion in brackets. Write resonance structures if necessary. a. BaCO3

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Textbook Question

A major challenge in implementing the 'hydrogen economy' is finding a safe, lightweight, and compact way of storing hydrogen for use as a fuel. The hydrides of light metals are attractive for hydrogen storage because they can store a high weight percentage of hydrogen in a small volume. For example, NaAlH4 can release 5.6% of its mass as H2 upon decomposing to NaH1s2, Al1s2, and H21g2. NaAlH4 possesses both covalent bonds, which hold polyatomic anions together, and ionic bonds. (d) What is the formal charge on hydrogen in the polyatomic ion?

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Textbook Question

Carbon ring structures are common in organic chemistry. Draw a Lewis structure for each carbon ring structure, including any necessary resonance structures. d. C6H6

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Textbook Question

Benzene has the following structural formula.

(b) Which statement best describes the carbon–carbon bonds in benzene? (i) Three carbon–carbon bonds are longer and weaker than the other three carbon–carbon bonds. (ii) All six carbon–carbon bonds are identical, and their length and strength are between a double and single bond. (iii) The length of carbon–carbon double bond switches back and forth between the length of a double and a single bond.

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Textbook Question

Draw three resonance structures for sulfur tetroxide, SO4, whose connections are shown below. (This is a neutral mol-ecule; it is not a sulfate ion.) Assign formal charges to the atoms in each structure.

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Textbook Question

The hypochlorite ion, ClO-, is the active ingredient in bleach. The perchlorate ion, ClO4-, is a main component of rocket propellants. Draw Lewis structures for both ions. (b) What is the formal charge of Cl in the perchlorate ion, assuming the Cl—O bonds are all single bonds?

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Textbook Question

The following three Lewis structures can be drawn for N2O:

(b) The N¬N bond length in N2O is 112 pm, slightly longer than a typical N‚N bond; and the N¬O bond length is 119 pm, slightly shorter than a typical N'O bond (see Table 8.4). Based on these data, which resonance structure best represents N2O?

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Textbook Question

Diazomethane is a highly poisonous, explosive compound because it readily evolves N2. Diazomethane has the following composition by mass: 28.57% C; 4.80% H; and 66.64% N. The molar mass of diazomethane is 42.04 g/mol. Find the molecular formula of diazomethane, draw its Lewis structure, and assign formal charges to each atom. Why is diazomethane not very stable? Explain.

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Textbook Question

Four different structures (a), (b), (c), and (d) can be drawn for compounds named dibromobenzene, but only three different compounds actually exist. Explain. (a)

(b)

(c)

(d)

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Textbook Question

1,2-dihydroxybenzene is obtained when two of the adjacent hydrogen atoms in benzene are replaced with an OH group. A skeleton of the molecule is shown here. (b) Are there any resonance structures for the molecule? If so, sketch them.

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Textbook Question

The cyanate ion (OCN- ) and the fulminate ion (CNO- ) share the same three atoms but have vastly different properties. The cyanate ion is stable, while the fulminate ion is unstable and forms explosive compounds. The resonance structures of the cyanate ion are explored in Example 9.8. Draw Lewis structures for the fulminate ion—including possible resonance forms— and use formal charge to explain why the fulminate ion is less stable (and therefore more reactive) than the cyanate ion.

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Textbook Question

Assign formal charges to the atoms in the following structures. Which of the two do you think is the more important contributor to the resonance hybrid? (a)

(b)

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Textbook Question

Sodium azide is a shock-sensitive compound that releases N2 upon physical impact. The compound is used in automobile airbags. The azide ion is N3-. (a) Draw the Lewis structure of the azide ion that minimizes formal charge (it does not form a triangle). Is it linear or bent? Draw the Lewis structure of the azide ion that minimizes formal charge (it does not form a triangle).

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Textbook Question

Draw the resonance structure indicated by the curved arrows. Assign formal charges, and evaluate which of the two structures is a larger contributor to the resonance hybrid.

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Textbook Question

The structure of borazine, B3N3H6, is a six-membered ring of alternating B and N atoms. There is one H atom bonded to each B and to each N atom. The molecule is planar. (a) Write a Lewis structure for borazine in which the formal charge on every atom is zero.

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Textbook Question

The azide ion, N3- , is a symmetrical ion, all of whose contributing resonance structures have formal charges. Draw three important contributing structures for this ion.

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Textbook Question

In the cyanate ion, OCN-, carbon is the central atom. (b) Which resonance structure makes the greatest contribution to the resonance hybrid? Which makes the least contribution? Explain.

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Textbook Question

The dichromate ion, Cr2O72-, has neither Cr¬Cr nor O¬O bonds. (a) Taking both 4s and 3d electrons into account, draw an electron-dot structure that minimizes the formal charges on the atoms.

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Textbook Question

Sulfur tetrafluoride 1SF42 reacts slowly with O2 to form sulfur tetrafluoride monoxide 1OSF42 according to the following unbalanced reaction: SF41g2 + O21g2¡OSF41g2 The O atom and the four F atoms in OSF4 are bonded to a central S atom. (b) Write a Lewis structure of OSF4 in which the formal charges of all atoms are zero.

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Open Question

Which resonance forms of silicon dioxide contribute the most to the actual bonding?

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Open Question

Using formal charges, which of these three resonance forms is likely to be the most important?

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Open Question

Draw the Lewis structures for three resonance forms of the nitrate ion, NO^-3. Include electron lone pairs, and any formal charges.

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