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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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?
Barium azide has molecular formula Ba(N3)2. Draw three resonance structures for the azide ion. Which structure is most important? Predict the relative bond lengths and bond strengths in the ion
An carbon-to-oxygen single bond (i.e. C-O) has a bond energy of 358 kJ/mol and an carbon-to-oxygen double bond (i.e. C=O) has a bond energy of 749 kJ/mol. Estimate the value of the carbon-to-oxygen bond energy in the carbonate anion, CO32— .
Hint: draw the Lewis structure of CO32— , consider resonance and determine which type of bonds it has. Because of the resonance, the bond between C and O will be somewhere in between the single and double bond.
Group of answer choices
1107 kJ/mol
358 kJ/mol
488 kJ/mol
928 kJ/mol
1465 kJ/mol
618 kJ/mol
749 kJ/mol
554 kJ/mol
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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- Write 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_forwardNitrosyl azide, N4O, is a pale yellow solid first synthesized in 1993. Write the Lewis structure for nitrosyl azide.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
- In which of the following molecules does the sulfur have an expanded octet? For those that do, write the Lewis structure. (a) SO2 (b) SF4 (c) SO2Cl2 (d) SF6arrow_forwardSelenium tetrafluoride, SeF₄, is a colorless liquid that is used as a fluorinating reagent in organic synthesis. Based on your Lewis structure for SeF₄, how many electron domains are on the central atom?arrow_forwardPure HN3 (atom sequence HNNN) is explosive. In aqueous solution, it is a weak acid that yields the azide ion, N3. Draw resonance structures to explain why the nitrogen-nitrogen bond lengths are equal in N3 but unequal in HN3.arrow_forward
- There are two main types of covalent bond breakage. In ho-molytic breakage , each atom in the bond gets one of the shared electrons. In some cases, the electronega-tivity of adjacent atoms affects the bond energy. In heterolytic breakage, one atom gets both electrons and the other gets none;thus, a cation and an anion form. (a) Why is the C−C bond in H₃C−CF₃(423 kJ/mol) strongerthan that in H₃C−CH₃(376 kJ/mol)?(b) Use bond energy and any other data to calculate the heat ofreaction for the heterolytic cleavage of O₂.arrow_forwardConsider peroxynitrite (chemical formula: ONOO−), a structural isomer of the nitrate anion. It is generated in the cell when nitric oxide (NO) reacts with the superoxide radical anion (O2-.). Peroxynitrite is a potent oxidant and nitrating agent and can lead to DNA and protein damage (this is the complete question) Draw the correct Lewis structure for peroxynitrite and indicate approximate bond angles. Tell how many molecular degrees of freedom of motion are present in peroxynitrite and what motions they correspond to.arrow_forwardWrite a Lewis structure for the NO3 - ion. Include resonance structures?arrow_forward
- Sulfur tetrafluoride reacts slowly with oxygen gas to form sulfur tetrafluoride monoxide. Write a balanced chemical equation for the reaction. In the sulfur tetrafluoride monoxide molecule the O atom and the four F atoms are bonded to a central S atom. Write a Lewis structure for this molecule in which the formal charges of all atoms is zero. Use bond energies to estimate the enthalpy of the above reaction. (S-F bond energy = 327 kJ/mole). Is it endothermic or exothermic? Determine the electron geometry of the molecule and predict two possible molecular geometries. Which of the two molecular geometries in part d is more likely to be observed? Explain.arrow_forwardOxygen gas reacts with sulfur tetrafluoride to slowly form sulfur tetrafluoride monoxide gas. Balance the equation for the formation of sulfur tetrafluoride monoxide. chemical reaction: 0,(g) + SF (g) → OSF,(g) Draw the Lewis structure of OSF, where the formal charge is zero on each atom. The sulfur atom is the central atom in the structure, and it is bonded to the oxygen atom and each of the four fluorine atoms. Select Draw Rings More Erase Use the bond energies in the table to estimate the enthalpy of reaction for the formation of sulfur tetrafluoride monoxide. étv Aaarrow_forwardHydrazine, N2H4, burns in oxygen as follows: N2H4 + O2 → N2 + 2H2O [The bond energies in kJ/mol are: N-H = 388; N-N 163; N≡N 944; O-H 463; O=O 496] Draw the chemical structures of the reactants and products and give the formula to calculate enthalpy change in a reaction, ΔH.arrow_forward
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