ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 1, Problem 1.53P
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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ClO2F2+
Chapter 1 Solutions
ORGANIC CHEMISTRY
Ch. 1 - While the most common isotope of nitrogen has a...Ch. 1 - Label each bond in the following compounds as...Ch. 1 - How many covalent bonds are predicted for each...Ch. 1 - Draw a valid Lewis structure for each species. a....Ch. 1 - Draw an acceptable Lewis structure for each...Ch. 1 - Prob. 1.6PCh. 1 - Draw a Lewis structure for each ion. a. CH3Ob....Ch. 1 - Prob. 1.8PCh. 1 - Draw Lewis structures for each molecular formula....Ch. 1 - Classify each pair of compounds as isomers or...
Ch. 1 - Prob. 1.11PCh. 1 - Prob. 1.12PCh. 1 - Prob. 1.13PCh. 1 - Draw a second resonance structure for each species...Ch. 1 - Prob. 1.15PCh. 1 - Prob. 1.16PCh. 1 - Prob. 1.17PCh. 1 - Prob. 1.18PCh. 1 - Using the principles of VSEPR theory, you can...Ch. 1 - Convert each condensed formula to a Lewis...Ch. 1 - Prob. 1.21PCh. 1 - Prob. 1.22PCh. 1 - Convert each skeletal structure to a complete...Ch. 1 - What is the molecular formula of quinine, the...Ch. 1 - Draw in all hydrogens and lone pairs on the...Ch. 1 - Prob. 1.26PCh. 1 - What orbitals are used to form each of the CC, and...Ch. 1 - What orbitals are used to form each bond in the...Ch. 1 - Determine the hybridization around the highlighted...Ch. 1 - The unmistakable odor of a freshly cut cucumber is...Ch. 1 - Prob. 1.31PCh. 1 - Rank the following atoms in order of increasing...Ch. 1 - Prob. 1.33PCh. 1 - Prob. 1.34PCh. 1 - Provide the following information about...Ch. 1 - Use the ball-and-stick model to answer each...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 carbon atom in the...Ch. 1 - Assign formal charges to each and atom in the...Ch. 1 - Prob. 1.41PCh. 1 - Prob. 1.42PCh. 1 - Prob. 1.43PCh. 1 - Draw all possible isomers for each molecular...Ch. 1 - 1.45 Draw Lewis structures for the nine isomers...Ch. 1 - Prob. 1.46PCh. 1 - Prob. 1.47PCh. 1 - Prob. 1.48PCh. 1 - Prob. 1.49PCh. 1 - Prob. 1.50PCh. 1 - Prob. 1.51PCh. 1 - Prob. 1.52PCh. 1 - Consider compounds A-D, which contain both a...Ch. 1 - Prob. 1.54PCh. 1 - Prob. 1.55PCh. 1 - 1.56 Consider the compounds and ions with curved...Ch. 1 - 1.57 Predict all bond angles in each...Ch. 1 - 1.58 Predict the geometry around each highlighted...Ch. 1 - Prob. 1.59PCh. 1 - Draw in all the carbon and hydrogen atoms in each...Ch. 1 - 1.61 Convert each molecule into a skeletal...Ch. 1 - Prob. 1.62PCh. 1 - Prob. 1.63PCh. 1 - Predict the hybridization and geometry around each...Ch. 1 - Prob. 1.65PCh. 1 - Ketene, , is an unusual organic molecule that has...Ch. 1 - Rank the following bonds in order of increasing...Ch. 1 - Prob. 1.68PCh. 1 - Two useful organic compounds that contain Cl atoms...Ch. 1 - Use the symbols + and to indicate the polarity of...Ch. 1 - Prob. 1.71PCh. 1 - Anacin is an over-the-counter pain reliever that...Ch. 1 - Answer the following questions about acetonitrile...Ch. 1 - Prob. 1.74PCh. 1 - 1.75 The principles of this chapter can be...Ch. 1 -
a. What is the hybridization of each N atom in...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. 1.80PCh. 1 - Prob. 1.81PCh. 1 - Prob. 1.82PCh. 1 - Prob. 1.83PCh. 1 - Prob. 1.84PCh. 1 - Prob. 1.85P
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- Draw 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_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_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
- Formic acid has the chemical formula HCOOH. It is a colorlessliquid that has a density of 1.220 g/mL. (a) The carbonatom in formic acid is bound to one H and both O’s. Drawthe Lewis structure for formic acid, showing resonance ifpresent. (b) Formic acid can react with NaOH in aqueoussolution to produce the formate ion, HCOO-. Write thebalanced chemical equation for this reaction. (c) Draw theLewis structure of the formate ion, showing resonance ifpresent. (d) How many milliliters of a 0.100 M solution ofNaOH would it take to completely react with 0.785 mL offormic acid?arrow_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? [Sections 8.3and 8.8]arrow_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
- 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_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_forwardConsider the collection of nonmetallic elements O, P, Te,I, and B. (a) Which two would form the most polar singlebond? (b) Which two would form the longest single bond?(c) Which two would be likely to form a compound of formulaXY2? (d) Which combinations of elements would likelyyield a compound of empirical formula X2Y3?arrow_forward
- Three resonance structures are possible for the thiocyanate ion, SCN-. (a) Draw the three resonance structures. (b) Calculate the formal charge on each atom in each resonance structures. (c) Based on formal charges and electronegativity, predict which resonance structure most closely approximates the bonding in this ion? (d) What are the similarities and differences of bonding in SCN compared to the bonding in OCN- .arrow_forward(a) Determine the formal charge of oxygen in the following structure. If the atom is formally neutral, indicate a charge of zero. (b) Draw an alternative Lewis (resonance) structure for the compound given in part (a). Show the unshared pairs and nonzero formal charges in your structure. Don't use radicals. Formal charge on O 0arrow_forwardAlthough I3- is a known ion, F3- is not. (a) Draw the Lewis structure for I3- (it is linear, not a triangle). (b) One of your classmates says that F3 - does not exist because F is too electronegative to make bonds with another atom. Give an example that proves your classmate is wrong. (c) Another classmate says F3- does not exist because it would violate the octet rule.Is this classmate possibly correct? (d) Yet another classmatesays F3- does not exist because F is too small to make bonds tomore than one atom. Is this classmate possibly correct?arrow_forward
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