Chemistry
13th Edition
ISBN: 9781259911156
Author: Raymond Chang Dr., Jason Overby Professor
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 9, Problem 9.96QP
Which of the following species are isoelectronic:
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Curved arrows are used to illustrate the flow of electrons. Using the provided
starting and product structures, draw the curved electron-pushing arrows for
the following reaction or mechanistic step(s).
Be sure to account for all bond-breaking and bond-making steps.
+
Drawing Arrows
CH3ONA, CH3OH
heat
: Br:O
Na →
H
H
Br
Na +
H
H
H
H
H
:0:
.H
+
Undo
Reset
Done
Q
CH3
Drag To Pan
+
What is the reaction mechanism for this?
20.19 Predict the structure of the major 1,2-addition product formed by reaction of one mole
of Cl₂ with 3-methylenecyclohexene. Also predict the structure of the 1,4-addition
product formed under these conditions.
20.20 Which of the two molecules shown do you expect to be the major product formed
by 1,2-addition of HCI to cyclopentadiene? Explain.
Cyclopentadiene
+ HC
3-Chlorocyclopentene
(racemic)
or
4-Chlorocyclopentene
(racemic)
Chapter 9 Solutions
Chemistry
Ch. 9.1 - Prob. 1RCFCh. 9.1 - Using only the periodic table, determine the Lewis...Ch. 9.1 - To what group on the periodic table does element X...Ch. 9.2 - Use Lewis dot symbols to represent the formation...Ch. 9.2 - Use Lewis dot symbols to represent the formation...Ch. 9.3 - Which of the following compounds has a larger...Ch. 9.3 - Arrange the compounds NaF, MgO, and AIN in order...Ch. 9.4 - Why is it not possible for hydrogen to form double...Ch. 9.4 - Arrange the bonds NN, NN, and NN in order of...Ch. 9.5 - Which of the following bonds is covalent, which is...
Ch. 9.5 - Rank the bonds BH, CCl, and PP in order of...Ch. 9.5 - Classify the following bonds as covalent, polar...Ch. 9.5 - Identify the electrostatic potential maps shown...Ch. 9.6 - Write the Lewis structure for carbon disulfide...Ch. 9.6 - Write the Lewis structure for formic acid (HCOOH).Ch. 9.6 - Write the Lewis structure for the nitrite ion...Ch. 9.6 - Write the Lewis structure for PCl3.Ch. 9.6 - Write the Lewis structure for CN.Ch. 9.6 - The molecular model shown here represents guanine,...Ch. 9.7 - Write formal charges for the nitrite ion (NO2).Ch. 9.7 - Draw the most reasonable Lewis structure of a...Ch. 9.7 - Write the formal charges on H, C, and N,...Ch. 9.7 - Write the formal charges on O and Cl,...Ch. 9.7 - Consider three possible atomic arrangements for...Ch. 9.8 - Draw three resonance structures for the...Ch. 9.8 - Draw three resonance structures for SO2.Ch. 9.8 - The molecular model shown here represents...Ch. 9.9 - Prob. 9PECh. 9.9 - Prob. 10PECh. 9.9 - Prob. 11PECh. 9.9 - Write the Lewis structure of sulfur tetrafluoride...Ch. 9.9 - Both boron and aluminum tend to form compounds in...Ch. 9.9 - Draw a Lewis structure for IF5.Ch. 9.9 - Prob. 3RCFCh. 9.10 - Calculate the enthalpy of the reaction...Ch. 9.10 - For the reaction H2(g)+C2H4(g)C2H6(g) (a) Estimate...Ch. 9.10 - Why does Hrxn calculated using bond enthalpies not...Ch. 9.10 - Using bond enthalpy values, predict the enthalpy...Ch. 9 - What is a Lewis dot symbol? To what elements does...Ch. 9 - Use the second member of each group from Group 1A...Ch. 9 - Prob. 9.3QPCh. 9 - Write Lewis dot symbols for the following ions:...Ch. 9 - Write Lewis dot symbols for the following atoms...Ch. 9 - Explain what an ionic bond is.Ch. 9 - Prob. 9.7QPCh. 9 - Name five metals and five nonmetals that are very...Ch. 9 - Name one ionic compound that contains only...Ch. 9 - Name one ionic compound that contains a polyatomic...Ch. 9 - Prob. 9.11QPCh. 9 - In which of the following states would NaCl be...Ch. 9 - Prob. 9.14QPCh. 9 - An ionic bond is formed between a cation A+ and an...Ch. 9 - Prob. 9.16QPCh. 9 - Use Lewis dot symbols to show the transfer of...Ch. 9 - Prob. 9.18QPCh. 9 - For each of the following pairs of elements, state...Ch. 9 - Prob. 9.20QPCh. 9 - What is lattice energy and what role does it play...Ch. 9 - Explain how the lattice energy of an ionic...Ch. 9 - Specify which compound in the following pairs of...Ch. 9 - Compare the stability (in the solid state) of the...Ch. 9 - Use the Born-Haber cycle outlined in Section 9.3...Ch. 9 - Calculate the lattice energy of calcium chloride...Ch. 9 - What is Lewiss contribution to our understanding...Ch. 9 - Use an example to illustrate each of the following...Ch. 9 - What is the difference between a Lewis dot symbol...Ch. 9 - How many lone pairs are on the underlined atoms in...Ch. 9 - Compare single, double, and triple bonds in a...Ch. 9 - Compare the properties of ionic compounds and...Ch. 9 - Define electronegativity, and explain the...Ch. 9 - List the following bonds in order of increasing...Ch. 9 - Arrange the following bonds in order of increasing...Ch. 9 - Four atoms are arbitrarily labeled D, E, F, and G....Ch. 9 - List the following bonds in order of increasing...Ch. 9 - Classify the following bonds as ionic, polar...Ch. 9 - Classify the following bonds as ionic, polar...Ch. 9 - Summarize the essential features of the Lewis...Ch. 9 - The octet rule applies mainly to the second-period...Ch. 9 - Write Lewis structures for the following molecules...Ch. 9 - Write Lewis structures for the following molecules...Ch. 9 - Write Lewis structures for the following...Ch. 9 - Write Lewis structures for the following...Ch. 9 - The following Lewis structures for (a) HCN, (b)...Ch. 9 - The skeletal structure of acetic acid shown here...Ch. 9 - Prob. 9.49QPCh. 9 - Do formal charges represent actual separation of...Ch. 9 - Write Lewis structures for the following ions: (a)...Ch. 9 - Write Lewis structures for the following ions: (a)...Ch. 9 - Define bond length, resonance, and resonance...Ch. 9 - Is it possible to trap a resonance structure of a...Ch. 9 - Write Lewis structures for the following species,...Ch. 9 - Draw three resonance structures for the chlorate...Ch. 9 - Write three resonance structures for hydrazoic...Ch. 9 - Draw two resonance structures for diazomethane,...Ch. 9 - Draw three resonance structures for the molecule...Ch. 9 - Draw three reasonable resonance structures for the...Ch. 9 - Why does the octet rule not hold for many...Ch. 9 - Give three examples of compounds that do not...Ch. 9 - Because fluorine has seven valence electrons...Ch. 9 - What is a coordinate covalent bond? Is it...Ch. 9 - Prob. 9.65QPCh. 9 - In the vapor phase, beryllium chloride consists of...Ch. 9 - Of the noble gases, only Kr, Xe, and Rn are known...Ch. 9 - Write a Lewis structure for SbCl5. Does this...Ch. 9 - Prob. 9.69QPCh. 9 - Write Lewis structures for the reaction...Ch. 9 - What is bond enthalpy? Bond enthalpies of...Ch. 9 - Explain why the bond enthalpy of a molecule is...Ch. 9 - From the following data, calculate the average...Ch. 9 - For the reaction O(g)+O2(g)O3(g)H=107.2kJ/mol...Ch. 9 - The bond enthalpy of F2(g) is 156.9 kJ/mol....Ch. 9 - For the reaction 2C2H6(g)+7O2(g)4CO2(g)+6H2O(g)...Ch. 9 - Prob. 9.77QPCh. 9 - Which of the following are ionic compounds? Which...Ch. 9 - Prob. 9.79QPCh. 9 - Use ionization energy (see Table 8.2) and electron...Ch. 9 - Prob. 9.82QPCh. 9 - Prob. 9.83QPCh. 9 - Write three reasonable resonance structures for...Ch. 9 - Prob. 9.85QPCh. 9 - Give an example of an ion or molecule containing...Ch. 9 - Draw four reasonable resonance structures for the...Ch. 9 - Prob. 9.88QPCh. 9 - Draw reasonable resonance structures for the...Ch. 9 - Are the following statements true or false? (a)...Ch. 9 - Prob. 9.91QPCh. 9 - Using the following information and the fact that...Ch. 9 - Prob. 9.93QPCh. 9 - Which of the following molecules has the shortest...Ch. 9 - Most organic acids can be represented as RCOOH,...Ch. 9 - Which of the following species are isoelectronic:...Ch. 9 - The following species have been detected in...Ch. 9 - The amide ion, NH2, is a Brnsted base. Represent...Ch. 9 - Draw Lewis structures for the following organic...Ch. 9 - The triiodide ion (I3) in which the I atoms are...Ch. 9 - Compare the bond enthalpy of F2 with the energy...Ch. 9 - Methyl isocyanate (CH3NCO) is used to make certain...Ch. 9 - Prob. 9.103QPCh. 9 - Prob. 9.104QPCh. 9 - Prob. 9.105QPCh. 9 - Draw Lewis structures for the following...Ch. 9 - Prob. 9.107QPCh. 9 - Prob. 9.108QPCh. 9 - Draw Lewis structures for the following organic...Ch. 9 - Write Lewis structures for the following four...Ch. 9 - Prob. 9.111QPCh. 9 - Prob. 9.112QPCh. 9 - Write three resonance structures for (a) the...Ch. 9 - (a) From the following data calculate the bond...Ch. 9 - Prob. 9.115QPCh. 9 - What are the other two reasons for choosing (b) in...Ch. 9 - Prob. 9.117QPCh. 9 - The NO bond distance in nitric oxide is 115 pm,...Ch. 9 - Prob. 9.119QPCh. 9 - Prob. 9.120QPCh. 9 - Prob. 9.121QPCh. 9 - Prob. 9.122QPCh. 9 - Draw a Lewis structure for nitrogen pentoxide...Ch. 9 - In the gas phase, aluminum chloride exists as a...Ch. 9 - The hydroxyl radical (OH) plays an important role...Ch. 9 - Experiments show that it takes 1656 kJ/mol to...Ch. 9 - Calculate Hrxn at 25C of the reaction between...Ch. 9 - Calculate Hrxn at 25C of the reaction between...Ch. 9 - Draw three resonance structures of sulfur dioxide...Ch. 9 - Vinyl chloride (C2H3Cl) differs from ethylene...Ch. 9 - Prob. 9.131QPCh. 9 - The American chemist Robert S. Mulliken suggested...Ch. 9 - Prob. 9.133QPCh. 9 - A student in your class claims that magnesium...Ch. 9 - Shown here is a skeletal structure of borazine...Ch. 9 - Calculate the wavelength of light needed to carry...Ch. 9 - Prob. 9.137QPCh. 9 - From the lattice energy of KCl in Table 9.1 and...Ch. 9 - The species H3+ is the simplest polyatomic ion....Ch. 9 - The bond enthalpy of the CN bond in the amide...Ch. 9 - In 1999 an unusual cation containing only nitrogen...Ch. 9 - Nitroglycerin, one of the most commonly used...Ch. 9 - Give a brief description of the medical uses of...Ch. 9 - Prob. 9.144QPCh. 9 - The isolated O2 ion is unstable so it is not...Ch. 9 - When irradiated with light of wavelength 471.7 nm,...Ch. 9 - Recall from Chapter 8 that the product of the...Ch. 9 - The reaction between fluorine (F2) with ethane...Ch. 9 - A new allotrope of oxygen, O4, has been reported....Ch. 9 - Because bond formation is exothermic, when two...Ch. 9 - Estimate Hf for sodium astatide (NaAt) according...
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- 20.35 Propose structural formulas for compounds A and B and specify the configuration of compound B. EtO₂C 250°C C14H2004 CO₂Et 1. Oso, then NaHSO3 2. HIO4 C14H2006 A Barrow_forward20.21 Predict the major product formed by 1,4-addition of HCI to cyclopentadiene. 20.22 Draw structural formulas for the two constitutional isomers with the molecular for- mula C₂H,Br, formed by adding one mole of Br, to cyclopentadiene.arrow_forwardAdd substituents to draw the conformer below (sighting down the indicated bond), then rotate the back carbon to provide the conformation that will be capable of an E2 elimination. R/S stereochemistry is graded. + I I H CH3 Ph Досн Br OCH 3 Drawing Q H Atoms, Bonds and Rings Charges Tap a node to see suggestions. H H H H H Undo Reset Remove Done Rotatearrow_forward
- 20.17 Predict the structure of the major product formed by 1,2-addition of HBr to 3-methylenecyclohexene. 3-Methylenecyclohexene 20.18 Predict the major product formed by 1,4-addition of HBr to 3-methylenecyclohexene.arrow_forward+ Draw a vicinal alkyl bromide that would produce the following alkene in an E2 elimination. Use a dash or wedge bond to indicate stereochemistry on asymmetric centers, where applicable. Ignore any inorganic byproducts. Br Drawing Strong Base H Q Atoms, Bonds Charges and Rings Draw or tap a new bond to see suggestions. Remove Done 語 Reset Undo + Drag To Panarrow_forwardDraw a vicinal alkyl bromide that would produce the following alkene in an E2 elimination. Use a dash or wedge bond to indicate stereochemistry on asymmetric centers, where applicable. Ignore any inorganic byproducts. + Drawing Į Strong Base H Br Q Atoms, Bonds and Rings Charges Draw or tap a new bond to see suggestions. Undo Reset 謂 Remove Done Drag To Pan +arrow_forward
- Draw the product of the E2 reaction shown below. Include the correct stereochemistry. Ignore any inorganic byproducts. + Br CH3 Q Strong Base Drawing Atoms, Bonds and Rings Charges Undo Reset H "Br H N Br. Remove Done .N. Drag To Panarrow_forwardCurved arrows are used to illustrate the flow of electrons. Use the reaction conditions provided and follow the curved arrows to draw the product of this elementary step in an elimination mechanism. Include all lone pairs and charges as appropriate. Ignore stereochemistry. Ignore byproducts. + Br: .. 8 0.01 M NaOH heat Drawing Q Atoms, Bonds and Rings Charges and Lone Pairs Draw or tap a new bond to see suggestions. Undo Reset Remove Done + Drag To Panarrow_forward+ Draw the product of the E2 reaction shown below. Include the correct stereochemistry. Ignore any inorganic byproducts. Ph CH2CH3 H H3C H Br DBN [૪] Drawing Atoms, Bonds and Rings H | OH Charges ―00 H. C | Undo Reset Br I Remove Done Drag To Pan +arrow_forward
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