Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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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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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 m = 1.5 D m = 0.2 D
(a) Use MO diagrams to place N2²+, N2+, N2 in order of decreasing bond energy.
O N, 2+
O N,2+
O N,2+
O N2+
O N2*
O N2+
>
O N2
O N2
O N2
(b) Use MO diagrams to place C2, C2, C2+ in order of decreasing bond length.
C2
O C2
C2
C2
C2
O C2
>
O C2+
O C2+
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
181 pm
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_forwardPhosphoserine is a less-common amino acid. (a) Identify the hybridizations of atoms I through 5. (b) What are the approximate values of the bond angles A, B. C, and D? (c) What are the most polar bonds in the molecule?arrow_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
- Explain in terms of bonding theory why all four hydrogen atoms of allene, H2CCCH2, cannot lie in the same plane.arrow_forwardIdentify the orbitals on each of the atoms that form the bonds in H3CCN. How many bonds and bonds form?arrow_forwardFluoromethane (CH3F, u=1.81 D) has a smaller dipole moment than chloromethane (CH3Cl u=1.87 D) even though fluorine is more electronegative than chlorine. Explain.arrow_forward
- 7) Which orbitals overlap to form the sigma and pi bonds in the following structure of carbon dioxide?arrow_forwardSort the following molecules by electron group geometry by dragging and dropping each symbolic representation into the appropriate box. Trigonal bipyramidal CIF3 SF6 PH3 H20 Octahedral Neither trigonal bipyramidal or octahedralarrow_forwardNonearrow_forward
- Consider the following molecules: A - BrCl B - SF4 C - BF3 D - F2 E - CF4 Which one of these molecules has bonds that are most polar? Which have a molecular dipole moment? BrCl SF4 BF3 F2 CF4arrow_forward39.098 40.078 Which one of the following diatomic species has a bond order of 3/2 (one and a half bond)? hydrogen 1 helium 2 H Не vil 1.0079 4.0026 beryllium 4 lithium boron carbon nitrogen охудеn fluorine neon 3 6 7 8 9 10 Li Be F Ne 9.0122 magnesium 12 14.007 phosphorus 15 6.941 10.811 aluminium 12.011 silicon 15.999 18.998 20.180 sodium sulfur chlorine argon 11 13 14 16 17 18 Na Mg AI Si CI Ar 22.990 potassium 19 24.305 calcium 26.982 gallium 31 28.086 germanium 32 30.974 chromium 24 nickel 28 32.065 selenium 35,453 bromine 39,948 kryplon 36 scandium titanium vanadium manganese iron cobalt copper zinc arsenic 20 21 22 23 25 26 27 29 30 33 34 35 K Ca Sc Ti Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br | Kr 44.956 yttrium 39 47.867 zirconium 40 50.942 niobium 51.996 molybdenum technetium 54.938 55.845 ruthenium 44 58.933 rhodium 63.546 silver 65.39 cadmium 48 69.723 Indium 74.922 antimony 51 79.904 lodine 83,80 rubidium 37 strontium 38 palladium 46 tin tellurium xenon 41 42 43 45 47 49 50 52 53…arrow_forward2barrow_forward
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