Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 1, Problem 1.69AP
Draw a Lewis structure for the azide ion, N3−. (The order of atom attachment is N─N─N, and they do not form a ring.) How does the resonance model account for the fact that the lengths of the N─N bonds in this ion are identical?
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Chapter 1 Solutions
Organic Chemistry
Ch. 1.1 - Prob. 1.1PCh. 1.2 - Prob. 1.2PCh. 1.2 - Judging from their relative positions in the...Ch. 1.2 - Classify each bond as nonpolar covalent or polar...Ch. 1.2 - Using the symbols and +, indicate the direction...Ch. 1.2 - Draw Lewis structures showing all valence...Ch. 1.2 - Draw Lewis structures for these ions and show...Ch. 1.3 - Draw Lewis structures and condensed structural...Ch. 1.3 - Prob. 1.9PCh. 1.3 - Prob. 1.10P
Ch. 1.3 - Prob. 1.11PCh. 1.3 - Prob. 1.12PCh. 1.4 - Predict all bond angles for these molecules. (a)...Ch. 1.5 - The geometry of carbon in diamond is tetrahedral,...Ch. 1.5 - Because of their spherical shape, C60 molecules...Ch. 1.5 - What best describes the CCC bond angles in C60? 1....Ch. 1.5 - Prob. 1.14PCh. 1.7 - Describe the bonding in these molecules in terms...Ch. 1.8 - Prob. 1.16PCh. 1.8 - Prob. 1.17PCh. 1.8 - Prob. 1.18PCh. 1.9 - Draw three contributing structures of the...Ch. 1.9 - What is the hybridization state of the circled...Ch. 1.9 - The molecule shown on the right in the example in...Ch. 1.9 - Prob. CQCh. 1.9 - The following structure is called imidazolium....Ch. 1 - Write the ground-state electron configuration for...Ch. 1 - Identify the atom that has each ground-state...Ch. 1 - Define valence shell and valence electron.Ch. 1 - How many electrons are in the valence shell of...Ch. 1 - Prob. 1.24PCh. 1 - Prob. 1.25PCh. 1 - Prob. 1.26PCh. 1 - Write Lewis structures for these compounds. Show...Ch. 1 - Write Lewis structures for these ions. Show all...Ch. 1 - Prob. 1.29PCh. 1 - Some of these structural formulas are incorrect...Ch. 1 - Following the rule that each atom of carbon,...Ch. 1 - Following are several Lewis structures showing all...Ch. 1 - Which statements are true about electronegativity?...Ch. 1 - Why does fluorine, the element in the upper right...Ch. 1 - Arrange the single covalent bonds within each set...Ch. 1 - Using the values of electronegativity given in...Ch. 1 - Prob. 1.37PCh. 1 - Use VSEPR to predict bond angles about each...Ch. 1 - Use VSEPR to predict bond angles about each atom...Ch. 1 - Use VSEPR to predict the geometry of these ions....Ch. 1 - Prob. 1.41PCh. 1 - Prob. 1.42PCh. 1 - What is the meaning of the term tertiary (3) when...Ch. 1 - What is the meaning of the term tertiary (3) when...Ch. 1 - Draw structural formulas for (a) The four primary...Ch. 1 - Draw structural formulas for the three tertiary...Ch. 1 - Prob. 1.47PCh. 1 - Identify the functional groups in each compound.Ch. 1 - Draw a three-dimensional representation for each...Ch. 1 - Tetrafluoroethylene, C2F4, is the starting...Ch. 1 - Which statements are true about resonance...Ch. 1 - Prob. 1.52PCh. 1 - Prob. 1.53PCh. 1 - Prob. 1.54PCh. 1 - Are the structures in each set valid contributing...Ch. 1 - State the orbital hybridization of each...Ch. 1 - Describe each highlighted bond in terms of the...Ch. 1 - Following is a structural formula of the...Ch. 1 - Draw a Lewis structure for methyl isocyanate,...Ch. 1 - What is the hybridization of the highlighted atoms...Ch. 1 - Using cartoon representations, draw a molecular...Ch. 1 - In what kind of orbitals do the lone-pair...Ch. 1 - Draw the delocalized molecular orbitals for the...Ch. 1 - Prob. 1.64APCh. 1 - Each compound contains both ions and covalent...Ch. 1 - Predict whether the carbon-metal bond in these...Ch. 1 - Prob. 1.67APCh. 1 - Phosphorus is immediately under nitrogen in the...Ch. 1 - Draw a Lewis structure for the azide ion, N3. (The...Ch. 1 - Cyanic acid, HOCN, and isocyanic acid, HNCO,...Ch. 1 - In Chapter 6, we study a group of organic cations...Ch. 1 - Many reactions involve a change in hybridization...Ch. 1 - Following is a structural formula of benzene,...Ch. 1 - Following are three contributing structures for...Ch. 1 - (a) Draw a Lewis structure for the ozone molecule,...Ch. 1 - The following two compounds are isomers; that is,...Ch. 1 - In future chapters, we will encounter...Ch. 1 - Prob. 1.78AP
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- Nitrosyl azide, N4O, is a pale yellow solid first synthesized in 1993. Write the Lewis structure for nitrosyl azide.arrow_forwardBond Enthalpy When atoms of the hypothetical element X are placed together, they rapidly undergo reaction to form the X2 molecule: X(g)+X(g)X2(g) a Would you predict that this reaction is exothermic or endothermic? Explain. b Is the bond enthalpy of X2 a positive or a negative quantity? Why? c Suppose H for the reaction is 500 kJ/mol. Estimate the bond enthalpy of the X2 molecule. d Another hypothetical molecular compound, Y2(g), has a bond enthalpy of 750 kJ/mol, and the molecular compound XY(g) has a bond enthalpy of 1500 kJ/mol. Using bond enthalpy information, calculate H for the following reaction. X2(g)+Y2(g)2XY(g) e Given the following information, as well as the information previously presented, predict whether or not the hypothetical ionic compound AX is likely to form. In this compound, A forms the A+ cation, and X forms the X anion. Be sure to justify your answer. Reaction: A(g)+12X2(g)AX(s)The first ionization energy of A(g) is 400 kJ/mol. The electron affinity of X(g) is 525 kJ/mol. The lattice energy of AX(s) is 100 kJ/mol. f If you predicted that no ionic compound would form from the reaction in Part e, what minimum amount of AX(s) lattice energy might lead to compound formation?arrow_forwardWrite all resonance structures of chlorobenzene, C6H5Cl, a molecule with the same cyclic structure as benzene. In all structures, keep the CCl bond as a single bond. Which resonance structures are the most important?arrow_forward
- Draw resonance structures for the SO2 molecule, and determine the formal charges on the S and O atoms. Are the SO bonds polar, and is the molecule as a whole polar? If so, what is the direction of the net dipole in SO2? Is your prediction confirmed by the electrostatic potential surface? Explain briefly.arrow_forwardWhat is the resonance form that describes the distribution of electrons in SeO2 ?arrow_forwardThe oxalate ion C2O42-, as the skeleton structure (a) Complete the Lewis structure of this ion. (b) Draw three possible resonance forms for C2O42-, equivalent to the Lewis structure drawn in (a). (c) Is a resonance form of the oxlate ion?arrow_forward
- Chemical species are said to be isoelectronic if they have the same Lewis structure (regardless of charge). Consider these ions and write a Lewis structure for a neutral molecule that is isoelectronic with them. (a) CN–, (b) NH4+ (c) CO3 2–arrow_forwardAn important observation supporting the concept of resonance in the localized electron model was that there are only three different structures of dichlorobenzene (C6H4C10). How does this fact support the concept of resonance (see Exercise 89)?arrow_forwardBest Lewis Formula and Molecular Geometry A student writes the Lewis electron-dot formula for the carbonate anion, CO32, as a Does this Lewis formula obey the octet rule? Explain. What are the formal charges on the atoms? Try describing the bonding for this formula in valence bond terms. Do you have any difficulty doing this? b Does this Lewis formula give a reasonable description of the electron structure, or is there a better one? If there is a better Lewis formula, write it down and explain why it is better. c The same student writes the following resonance description for CO2: Is there something wrong with this description? (What would you predict as the geometries of these formulas?) d Is one or the other formula a better description? Could a value for the dipole moment help you decide? e Can you write a Lewis formula that gives an even better description of CO2? Explain your answer.arrow_forward
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