Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 2.1B, Problem 2.2P
The N—F bond is more polar than the N—H bond: but NF3 has a smaller dipole moment than NH3. Explain this curious result
NH3 NF3
μ = 1 5 D μ = 0 2 D
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(a) Use MO diagrams to place N2²+, N2+, N2 in order of decreasing bond energy.
O N, 2+
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O N,2+
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O N2+
>
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O N2
(b) Use MO diagrams to place C2, C2, C2+ in order of decreasing bond length.
C2
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C2
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>
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6. Phosgene, Cl2C = O, has a lower dipole moment than formaldehyde H2C = O. Explain why.
Explain the trends in the bond angles and bond lengths of the following ions.
Bond length (X-O)
Bond Angle (O-X-0)
CIO3
149 pm
107°
165 pm
104°
BrO3
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100°
103
Chapter 2 Solutions
Organic Chemistry (9th Edition)
Ch. 2.1A - Prob. 2.1PCh. 2.1B - The NF bond is more polar than the NH bond: but...Ch. 2.1B - For each of the following compounds 1. Draw the...Ch. 2.1B - Two isomers of 1,2-dichloroethene are known One...Ch. 2.2C - Prob. 2.5PCh. 2.2C - Prob. 2.6PCh. 2.3 - Prob. 2.7PCh. 2.4 - Calculate the pH of the following solutions a....Ch. 2.6A - Ammonia appears in Table 2-2 as both an acid and a...Ch. 2.7 - Write equations for the following acid-base...
Ch. 2.7 - Ethanol, methylamine. and acetic acid are all...Ch. 2.8 - Prob. 2.12PCh. 2.10 - Write equations for the following acid-base...Ch. 2.10 - Rank the following acids in decreasing order of...Ch. 2.11 - Prob. 2.15PCh. 2.11 - Prob. 2.16PCh. 2.11 - Consider each pair of bases and explain which one...Ch. 2.12 - Which is a stronger base ethoxide ion or acetate...Ch. 2.12 - Prob. 2.19PCh. 2.12 - Prob. 2.20PCh. 2.12 - Prob. 2.21PCh. 2.12 - Choose the more basic member of each pair of...Ch. 2.14 - Prob. 2.23PCh. 2.15D - Classify the following hydrocarbons and draw a...Ch. 2.16D - Prob. 2.25PCh. 2.17C - Draw a Lewis structure and classify each of the...Ch. 2.17C - Circle the functional groups in the following...Ch. 2 - The CN triple bond in acetonitrile has a dipole...Ch. 2 - Prob. 2.29SPCh. 2 - Sulfur dioxide has a dipole moment of 1.60 D....Ch. 2 - Which of the following pure compounds can form...Ch. 2 - Predict which member of each pair is more soluble...Ch. 2 - Prob. 2.33SPCh. 2 - Prob. 2.34SPCh. 2 - Predict which compound in each pair has the higher...Ch. 2 - All of the following compounds can react as acids...Ch. 2 - Rank the following species in order of increasing...Ch. 2 - Rank the following species in order of increasing...Ch. 2 - The Ka of phenylacetic acid is 5 2 105, and the...Ch. 2 - The following compound can become protonated on...Ch. 2 - The following compounds are listed in increasing...Ch. 2 - Prob. 2.42SPCh. 2 - Prob. 2.43SPCh. 2 - Compare the relative acidity of 1-molar aqueous...Ch. 2 - The following compounds can all react as acids. a....Ch. 2 - The following compounds can all react as bases. a....Ch. 2 - The following compounds can all react as acids. a....Ch. 2 - Prob. 2.48SPCh. 2 - Methyllithium (CH3Li) is often used as a base in...Ch. 2 - Label the reactants in these acid-base reactions...Ch. 2 - In each reaction, label the reactants as Lewis...Ch. 2 - Prob. 2.52SPCh. 2 - Each of these compounds can react as a nucleophile...Ch. 2 - Prob. 2.54SPCh. 2 - Give a definition and an example for each class of...Ch. 2 - Circle the functional groups in the following...Ch. 2 - Prob. 2.57SP
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- Describe the molecular orbital configurations of C2, C2, and C22. What are the bond orders of these species? Arrange the three species by increasing bond length. Arrange the species by increasing bond enthalpy. Explain these arrangements of bond length and bond enthalpy.arrow_forwardPredict the molecular structure, bond angles, and polarity (has a net dipole moment or has no net dipole moment) for each of the following compounds. a. SeCl4 b. SO2 c. KrF4 d. CBr4 e. IF3 f. ClF3arrow_forwardIn the gas phase, positive and negative ions form ion pairs that are like molecules. An example is KF, which is found to have a dipole moment of 28.7 1030 C m and a distance of separation between the two ions of 217.2 pm. Use this information and the definition of dipole moment to calculate the partial charge on each atom. Compare your result with the expected charge, which is the charge on an electron, 1.602 1019 C. Based on your result, is KF really completely ionic?arrow_forward
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