Chemistry
13th Edition
ISBN: 9781259911156
Author: Raymond Chang Dr., Jason Overby Professor
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 9.6, Problem 1RCF
Write the Lewis structure for PCl3.
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Predict the organic products that form in the reaction below:
H.
H+
+
OH
H+
Y
Note: You may assume you have an excess of either reactant if the reaction requires more than one of those molecules to form the
products.
In the drawing area below, draw the skeletal ("line") structures of the missing organic products X and Y. You may draw the
structures in any arrangement that you like, so long as they aren't touching.
Explanation
Check
Click and drag to start drawing a
structure.
G
X
C
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+
111
Carbonyl Chem
Choosing reagants for a Wittig reaction
What would be the best choices for the missing reagents 1 and 3 in this synthesis?
1. PPh3
3
1
2
2. n-BuLi
• Draw the missing reagents in the drawing area below. You can draw them in any arrangement you like.
Do not draw the missing reagent 2. If you draw 1 correctly, we'll know what it is.
• Note: if one of your reagents needs to contain a halogen, use bromine.
Explanation
Check
Click and drag to start drawing a structure.
×
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A student proposes the transformation below in one step of an organic synthesis. There may be one or more reactants missing from the left-hand side, but there
are no products missing from the right-hand side. There may also be catalysts, small inorganic reagents, and other important reaction conditions missing from
the arrow.
• Is the student's transformation possible? If not, check the box under the drawing area.
. If the student's transformation is possible, then complete the reaction by adding any missing reactants to the left-hand side, and adding required catalysts,
inorganic reagents, or other important reaction conditions above and below the arrow.
• You do not need to balance the reaction, but be sure every important organic reactant or product is shown.
+
T
X
O
O
лет-ле
HO
OH
HO
OH
This transformation can't be done in one step.
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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- Determine the structures of the missing organic molecules in the following reaction: X+H₂O H* H+ Y OH OH Note: Molecules that share the same letter have the exact same structure. In the drawing area below, draw the skeletal ("line") structures of the missing organic molecules X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Click and drag to start drawing a structure. X Sarrow_forwardPredict the major products of this organic reaction. If there aren't any products, because nothing will happen, check the box under the drawing area instead. No reaction. HO. O :☐ + G Na O.H Click and drag to start drawing a structure. XS xs H₂Oarrow_forwardWhat are the angles a and b in the actual molecule of which this is a Lewis structure? H H C H- a -H b H Note for advanced students: give the ideal angles, and don't worry about small differences from the ideal groups may have slightly different sizes. a = b = 0 °arrow_forward
- What are the angles a and b in the actual molecule of which this is a Lewis structure? :0: HCOH a Note for advanced students: give the ideal angles, and don't worry about small differences from the ideal that might be caused by the fact that different electron groups may have slightly different sizes. a = 0 b=0° Sarrow_forwardDetermine the structures of the missing organic molecules in the following reaction: + H₂O +H OH O OH +H OH X Note: Molecules that share the same letter have the exact same structure. In the drawing area below, draw the skeletal ("line") structure of the missing organic molecule X. Click and drag to start drawing a structure.arrow_forwardIdentify the missing organic reactant in the following reaction: x + x O OH H* + ☑- X H+ O O Х Note: This chemical equation only focuses on the important organic molecules in the reaction. Additional inorganic or small-molecule reactants or products (like H₂O) are not shown. In the drawing area below, draw the skeletal ("line") structure of the missing organic reactant X. Click and drag to start drawing a structure. Carrow_forward
- CH3O OH OH O hemiacetal O acetal O neither O 0 O hemiacetal acetal neither OH hemiacetal O acetal O neither CH2 O-CH2-CH3 CH3-C-OH O hemiacetal O acetal CH3-CH2-CH2-0-c-O-CH2-CH2-CH3 O neither HO-CH2 ? 000 Ar Barrow_forwardWhat would be the best choices for the missing reagents 1 and 3 in this synthesis? 1. PPh3 2 2. n-BuLi 3 Draw the missing reagents in the drawing area below. You can draw them in any arrangement you like. • Do not draw the missing reagent 2. If you draw 1 correctly, we'll know what it is. • Note: if one of your reagents needs to contain a halogen, use bromine. Explanation Check Click and drag to start drawing a structure.arrow_forwardPredict the products of this organic reaction: NaBH3CN + NH2 ? H+ Click and drag to start drawing a structure. ×arrow_forward
- Predict the organic products that form in the reaction below: + OH +H H+ ➤ ☑ X - Y Note: You may assume you have an excess of either reactant if the reaction requires more than one of those molecules to form the products. In the drawing area below, draw the skeletal ("line") structures of the missing organic products X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Click and drag to start drawing a structure. Garrow_forwardPredict the organic products that form in the reaction below: OH H+ H+ + ☑ Y Note: You may assume you have an excess of either reactant if the reaction requires more than one of those molecules to form the products. In the drawing area below, draw the skeletal ("line") structures of the missing organic products X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Click and drag to start drawing a structure. ✓ marrow_forwardDetermine the structures of the missing organic molecules in the following reaction: + H₂O +H H+ Y Z ☑ ☑ Note: Molecules that share the same letter have the exact same structure. In the drawing area below, draw the skeletal ("line") structures of the missing organic molecules X, Y, and Z. You may draw the structures in any arrangement that you like, so long as they aren't touching. Molecule X shows up in multiple steps, but you only have to draw its structure once. Click and drag to start drawing a structure. AP +arrow_forward
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