EBK CHEMISTRY: THE MOLECULAR NATURE OF
7th Edition
ISBN: 9781119513216
Author: HYSLOP
Publisher: JOHN WILEY+SONS INC.
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Textbook Question
Chapter 8, Problem 22RQ
What factors control the bond length in a covalent bond?
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Kumada Coupling:
1. m-Diisobutylbenzene below could hypothetically be synthesized by Friedel-Crafts reaction. Write out the reaction with a
mechanism and give two reasons why you would NOT get the desired product.
Draw the reaction (NOT a mechanism) for a Kumada coupling to produce the molecule above from m-dichlorobenzene.
Calculate the theoretical yield for the reaction in question 2 using 1.5 g of p-dichlorobenzene and 3.0 mL isobutyl bromide.
What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What
other impurities are present in your product and how do you know?
Wintergreen from Aspirin:
1. In isolating the salicylic acid, why is it important to press out as much of the water as possible?
2. Write the mechanism of the esterification reaction you did.
3.
What characteristic absorption band changes would you expect in the IR spectrum on going from aspirin to salicyclic acid and
then to methyl salicylate as you did in the experiment today? Give approximate wavenumbers associated with each functional
group change.
What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What
other impurities are present in your product and how do you know?
Synthesis of ZybanⓇ:
1. Write a mechanism for the bromination of m-chloropropiophenone.
Br₂
CH2Cl2
Cl
Br
2. Give the expected m/z (to a round number) for the molecular ion from the product above (including isotopic peaks).
3. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What
other impurities are present in your product and how do you know?
Chapter 8 Solutions
EBK CHEMISTRY: THE MOLECULAR NATURE OF
Ch. 8 - Practice Exercise 8.1
Choose the ionic compound...Ch. 8 - Construct an energy diagram similar to the one in...Ch. 8 - What is wrong with the following electron...Ch. 8 - How do the electron configurations change when a...Ch. 8 - Practice Exercise 8.5
How are the electron...Ch. 8 - Practice Exercise 8.6
Draw the Lewis structures...Ch. 8 - Practice Exercise 8.7
Use Lewis symbols to diagram...Ch. 8 - Prob. 8PECh. 8 - Prob. 9PECh. 8 - For each atom that does not have an octet, how...
Ch. 8 - The chlorine end of the chlorine monoxide molecule...Ch. 8 - Although isolated Na+ and Cl- ions are unstable,...Ch. 8 - Bromine and chlorine form a molecular substance...Ch. 8 - Practice Exercise 8.14
For each of the following...Ch. 8 - Prob. 15PECh. 8 - Draw Lewis structures for...Ch. 8 - Practice Exercise 8.17
Using the structures drawn...Ch. 8 - Practice Exercise 8.18
A student drew the...Ch. 8 - Assign formal charges to the atoms in the...Ch. 8 - Practice Exercise 8.20
Draw the preferred Lewis...Ch. 8 - Prob. 21PECh. 8 - Practice Exercise 8.22
Use Lewis structures to...Ch. 8 - Prob. 23PECh. 8 - Practice Exercise 8.24
Draw the resonance...Ch. 8 - Determine the preferred Lewis structure for the...Ch. 8 - Prob. 26PECh. 8 - Practice Exercise 8.27
The following questions...Ch. 8 - What must be true about the change in the total...Ch. 8 - 8.2 Under what conditions could a compound form...Ch. 8 - 8.3 What is an ionic bond?
Ch. 8 - Define the term lattice energy. In what ways does...Ch. 8 - How is the tendency to form ionic bonds related to...Ch. 8 - What influence do ion size and charge have on...Ch. 8 - 8.7 What is the octet rule? What is responsible...Ch. 8 - 8.8 Why doesn’t hydrogen obey the octet rule?
Ch. 8 - 8.9 Magnesium forms compounds containing the ion ...Ch. 8 - Prob. 10RQCh. 8 - Why do many of the transition elements in Period 4...Ch. 8 - Prob. 12RQCh. 8 - Prob. 13RQCh. 8 - Which of these Lewis symbols is incorrect?Ch. 8 - Define bond length and bond energy.Ch. 8 - 8.16 Define bond order. How are bond energy and...Ch. 8 - 8.17 The energy required to break the H—Cl bond to...Ch. 8 - In terms of the potential energy change, why...Ch. 8 - Prob. 19RQCh. 8 - Describe what happens to the electron density...Ch. 8 - Is the formation of a covalent bond endothermic or...Ch. 8 - What factors control the bond length in a covalent...Ch. 8 - How many covalent bonds are normally formed by (a)...Ch. 8 - What is a polar covalent bond?Ch. 8 - Define dipole moment in the form of an equation....Ch. 8 - 8.26 Define electronegativity. On what basis did...Ch. 8 - Which element has the highest electronegativity?...Ch. 8 - Prob. 28RQCh. 8 - If an element has a low electronegativity, is it...Ch. 8 - In what groups in the periodic table are the most...Ch. 8 - How is the electronegativity of a metal related to...Ch. 8 - 8.32 When we say that aluminum is more reactive...Ch. 8 - Arrange the following metals in their approximate...Ch. 8 - 8.34 Complete and balance the following equations....Ch. 8 - Prob. 35RQCh. 8 - Without looking at the text, describe the steps...Ch. 8 - 8.37 Why do we usually place the least...Ch. 8 - Why do Period 2 elements never form more than four...Ch. 8 - Define (a) single bond, (b) double bond, and (c)...Ch. 8 - Prob. 40RQCh. 8 - How many electrons are in the valence shells of...Ch. 8 - What is the minimum number of electrons that would...Ch. 8 - 8.43 Nitrogen and arsenic are in the same group in...Ch. 8 - 8.44 What is the definition of formal charge? How...Ch. 8 - How are formal charges for atoms in a molecule...Ch. 8 - 8.46 How are formal charges used to select the...Ch. 8 - 8.47 What are the formal charges on the atoms in...Ch. 8 - What is a coordinate covalent bond?Ch. 8 - Once formed, how (if at all) does a coordinate...Ch. 8 - BC13 has an incomplete valence shell. Use Lewis...Ch. 8 - Prob. 51RQCh. 8 - 8.52 What is a resonance hybrid? How does it...Ch. 8 - Prob. 53RQCh. 8 - Polystyrene plastic is a hydrocarbon that consists...Ch. 8 - Sketch the structures for (a) methane, (b) ethane,...Ch. 8 - Draw the structure for a hydrocarbon that has a...Ch. 8 - How many different molecules have the formula...Ch. 8 - What is a carbonyl group? In which classes of...Ch. 8 - Prob. 59RQCh. 8 - 8.60 Write a chemical equation for the ionization...Ch. 8 - Match the compounds on the left with the family...Ch. 8 - Prob. 62RQCh. 8 - In each of the following pairs of compounds, which...Ch. 8 - In each of the following pairs of compounds, which...Ch. 8 - Prob. 65RQCh. 8 - *8.66 Use an enthalpy diagram to calculate the...Ch. 8 - Explain what happens to the electron...Ch. 8 - Describe what happens to the electron...Ch. 8 - 8.69 What are the electron configurations of the ...Ch. 8 - 8.70 What are the electron configurations of the ...Ch. 8 - Write the abbreviated electron configuration of...Ch. 8 - Write the abbreviated electron configuration of...Ch. 8 - Prob. 73RQCh. 8 - Prob. 74RQCh. 8 - Prob. 75RQCh. 8 - Prob. 76RQCh. 8 - How much energy, in joules, is required to break...Ch. 8 - How much energy is released in the formation of...Ch. 8 - The reason there is danger in exposure to...Ch. 8 - A mixture of H2andCl2 is stable, but a bright...Ch. 8 - Prob. 81RQCh. 8 - Use Lewis structures to diagram the formation of...Ch. 8 - Chlorine tends to form only one covalent bond...Ch. 8 - Use the octet rule to predict the formula of the...Ch. 8 - Prob. 85RQCh. 8 - What would be the formula for the simplest...Ch. 8 - 8.87 Use the data in Table 8.3 to calculate the...Ch. 8 - The molecule bromine monofluoride has a dipole...Ch. 8 - Prob. 89RQCh. 8 - 8.90 The dipole moment of HF is 1.83 D and the...Ch. 8 - Prob. 91RQCh. 8 - Prob. 92RQCh. 8 - Which of the bonds in Problem 8.91 is the most...Ch. 8 - 8.94 Which of the bonds in the Problem 8.92 is the...Ch. 8 - Draw Lewis structures for...Ch. 8 - Draw Lewis structures for...Ch. 8 - Prob. 97RQCh. 8 - 8.98 Draw Lewis structures for
Ch. 8 - 8.99 Draw Lewis structures for (a) carbon...Ch. 8 - Draw Lewis structures for (a) selenium trioxide,...Ch. 8 - Prob. 101RQCh. 8 - 8.102 Draw Lewis structures for .
Ch. 8 - Draw the Lewis structure for (a) CH2O (the central...Ch. 8 - Draw Lewis structures for (a) the peroxide ion,...Ch. 8 - Assign formal charges to each atom in the...Ch. 8 - 8.106 Assign formal charges to each atom in the...Ch. 8 - Draw the Lewis structure for HCIO4. Assign formal...Ch. 8 - Draw the Lewis structure for SOCl2 (sulfur bonded...Ch. 8 - Prob. 109RQCh. 8 - 8.110 The following are two Lewis structures that...Ch. 8 - 8.111 Use Lewis structures to show that the...Ch. 8 - Use Lewis structures to show that the reaction...Ch. 8 - Draw all of the resonance structures for the N2O4...Ch. 8 - Prob. 114RQCh. 8 - How should the NO bond lengths compare in the NO3...Ch. 8 - Arrange the following in order of increasing CO...Ch. 8 - 8.117 The Lewis structure of was given as
but...Ch. 8 - *8.118 Use formal charges to establish the...Ch. 8 - 8.119 Give the formula and name of four different...Ch. 8 - Use data from the tables of ionization energies...Ch. 8 - 8.121 Changing to gaseous atoms requires a total...Ch. 8 - In many ways, tin(IV) chloride behaves more like a...Ch. 8 - In each pair, choose the one with the more polar...Ch. 8 - How many electrons are in the outer shell of the...Ch. 8 - Prob. 125RQCh. 8 - 8.126 Are the following Lewis structures...Ch. 8 - Assign formal charges to all the atoms in the...Ch. 8 - 8.128 Assign formal charges to all the atoms in...Ch. 8 - The inflation of an air bag when a car experiences...Ch. 8 - 8.130 How should the sulfur-oxygen bond lengths...Ch. 8 - What is the most reasonable Lewis structure for...Ch. 8 - Prob. 132RQCh. 8 - Prob. 133RQCh. 8 - 8.134 Below is a ball-and-stick model of a type of...Ch. 8 - 8.135 Explain why ions of the representative...Ch. 8 - Use Lewis structures to show the ionization of the...Ch. 8 - The compound below, an amine, is a weak base and...Ch. 8 - 8.138 Use Lewis structures to diagram the reaction...Ch. 8 - How many grams of water could have its temperature...Ch. 8 - Prob. 140RQCh. 8 - A 38.40 mg sample of an organic acid composed of...Ch. 8 - What is the average bond energy of a CC covalent...Ch. 8 - One way of estimating the electronegativity of an...Ch. 8 - 8.144 The attractions between molecules of a...Ch. 8 - The positive end of the dipole in a water molecule...Ch. 8 - In describing the structures of molecules, we use...
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