ORGANIC CHEMISTRY (LOOSELEAF)
6th Edition
ISBN: 9781260475630
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 1, Problem 56P
Consider compounds A-D, which contain both a heteroatom and a double bond. (a) For which compounds are no additional Lewis structures possible? (b) When two or more Lewis structures can be drawn, draw all additional resonance structures.
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Chapter 1 Solutions
ORGANIC CHEMISTRY (LOOSELEAF)
Ch. 1.1 - While the most common isotope of nitrogen has a...Ch. 1.2 - Label each bond in the following compounds as...Ch. 1.3 - Draw a valid Lewis structure for each species. a....Ch. 1.3 - Prob. 9PCh. 1.4 - Draw Lewis structures for each molecular formula....Ch. 1.6 - Classify each pair of compounds as isomers or...Ch. 1.6 - Prob. 12PCh. 1.6 - Prob. 13PCh. 1.6 - Prob. 14PCh. 1.6 - Prob. 16P
Ch. 1.6 - Prob. 17PCh. 1.7 - Prob. 18PCh. 1.7 - Prob. 19PCh. 1.7 - Using the principles of VSEPR theory, you can...Ch. 1.8 - Convert each condensed formula to a Lewis...Ch. 1.8 - Prob. 22PCh. 1.8 - Prob. 23PCh. 1.8 - Convert each skeletal structure to a complete...Ch. 1 - Citric acid is responsible for the tartness of...Ch. 1 - Zingerone gives ginger its pungent taste. a.What...Ch. 1 - Assign formal charges to each and atom in the...Ch. 1 - Prob. 44PCh. 1 - Prob. 46PCh. 1 - Draw all possible isomers for each molecular...Ch. 1 - 1.45 Draw Lewis structures for the nine isomers...Ch. 1 - Prob. 52PCh. 1 - Prob. 53PCh. 1 - Prob. 54PCh. 1 - Consider compounds A-D, which contain both a...Ch. 1 - Draw in all the carbon and hydrogen atoms in each...Ch. 1 - 1.61 Convert each molecule into a skeletal...Ch. 1 - Prob. 65PCh. 1 - Predict the hybridization and geometry around each...Ch. 1 - Prob. 68PCh. 1 - Ketene, , is an unusual organic molecule that has...Ch. 1 - Rank the following bonds in order of increasing...Ch. 1 - Two useful organic compounds that contain Cl atoms...Ch. 1 - Use the symbols + and to indicate the polarity of...Ch. 1 - Prob. 74PCh. 1 - Anacin is an over-the-counter pain reliever that...Ch. 1 - 1.77 Stalevo is the trade name for a medication...Ch. 1 - 1.78 and are two highly reactive carbon...Ch. 1 - 1.79 The N atom in (acetamide) is hybridized,...Ch. 1 - Prob. 83PCh. 1 - Prob. 84PCh. 1 - Prob. 85PCh. 1 - Prob. 86PCh. 1 - Prob. 87PCh. 1 - Prob. 88P
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- Consider compounds A–D, which contain both a heteroatom and a double bond. (a) For which compounds are no additional Lewis structures possible? (b) When two or more Lewis structures can be drawn, draw all additional resonance structures.arrow_forwardA stable triatomic molecule can be formed that containsone atom each of nitrogen, sulfur, and fluorine. Threebonding structures are possible, depending on which is thecentral atom: NSF, SNF, and SFN.(a) Write a Lewis diagram for each of these molecules,indicating the formal charge on each atom.(b) Often, the structure with the least separation of formal charge is the most stable. Is this statement consistent with the observed structure for this molecule—namely, NSF, which has a central sulfur atom?(c) Does consideration of the electronegativities of N, S,and F from Figure 3.18 help rationalize this observedstructure? Explain.arrow_forwardDraw Lewis structures for each of the following compounds. In each case, specify the number of valence electrons surrounding the central atom. (Assign lone pairs and radical electrons where appropriate.) (Assume the central atom does not contain an expanded octet.) (a) bromine dioxide (BrO2) (b) beryllium bromide (BeBr2) (c) phosphorus pentafluoride (PF5)arrow_forward
- Finish the following questions. ((a) Draw all of the possible Lewis structures (including reasonance structures) of the following compounds.(b) Label the formal charge for each atom.(c) Determine which resonance structure(s) is(are) the better/best and briefly explain. ClO2F2+arrow_forwardThe molecular ion S3N, has the cyclic structure 'N All S-N bonds are equivalent. (a) Give six equivalent resonance hybrid Lewis diagrams for this molecular ion. (b) Compute the formal charges on all atoms in the molecular ion in each of the six Lewis diagrams. (c) Determine the charge on each atom in the polyatomic ion, assuming that the true distribution of electrons is the average of the six Lewis diagrams arrived at in parts (a) and (b). (d) An advanced calculation suggests that the actual charge resident on each N atom is –0.375 and on each S atom is +0.041. Show that this result is consis- tent with the overall +1 charge on the molecular ion. Z-Sarrow_forwardThe partial Lewis structure that follows is for a hydrocarbonmolecule. In the full Lewis structure, each carbon atomsatisfies the octet rule, and there are no unshared electronpairs in the molecule. The carbon—carbon bondsare labeled 1, 2, and 3. (a) How many hydrogen atomsare in the molecule? (b) Rank the carbon–carbonbonds in order of increasing bond length. (c) Whichcarbon—carbon bond is the strongest one?arrow_forward
- The partial Lewis structure that follows is for a hydrocarbonmolecule. In the full Lewis structure, each carbon atomsatisfies the octet rule, and there are no unshared electronpairs in the molecule. The carbon—carbon bondsare labeled 1, 2, and 3. (a) How many hydrogen atomsare in the molecule? (b) Rank the carbon–carbonbonds in order of increasing bond length. (c) Whichcarbon—carbon bond is the strongest one? [Sections 8.3and 8.8]arrow_forwardSome chemists believe that satisfaction of the octet rule should be the top criterion for choosing the dominant Lewis structure of a molecule or ion. Other chemists believe that achieving the best formal charges should be the top criterion. Consider the dihydrogen phosphate ion, HaPO, , in which the H atoms are bonded to O atoms. (a) What is the predicted dominant Lewis structure if satisfying the octet rule is the top eriterion? (b) What is the predicted dominant Lewis structure if achieving the best formal charges is the top criterion?arrow_forward(a) Draw a second resonance structure for A. (b) Why can't a second resonance structure be drawn for B?arrow_forward
- The structure at the right is a skeleton of an anion having the overall formula C6H,NO¯. The hydrogen atoms are not shown. (a) Draw a complete Lewis structure in which the -1 formal charge is on N. Include all H atoms and C. valence electrons. (b) Do the same for a Lewis structure with the -1 formal charge on O. (c) Do the same for a Lewis structure with the -1 formal charge on the C atom that is bonded to three other C atoms.arrow_forward(a) Describe the molecule xenon trioxide, XeO3, using four possible Lewis structures, one each with zero, one, two, or three Xe—O double bonds. (b) Do any of these resonance structures satisfy the octet rule for every atom in the molecule? (c) Do any of the four Lewis structures have multiple resonance structures? If so, how many resonance structures do you find? (d) Which of the Lewis structures in (a) yields the most favorable formal charges for the molecule?arrow_forwardThe hypochlorite ion, ClO-, is the active ingredient inbleach. The perchlorate ion, ClO4-, is a main componentof rocket propellants. Draw Lewis structures for both ions. (a) What is the formal charge of Cl in the hypochlorite ion?(b) What is the formal charge of Cl in the perchlorate ion, assumingthe Cl—O bonds are all single bonds? (c) What is theoxidation number of Cl in the hypochlorite ion? (d) Whatis the oxidation number of Cl in the perchlorate ion, assumingthe Cl—O bonds are all single bonds? (e) In a redox reaction,which ion would you expect to be more easily reduced?arrow_forward
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