ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 1, Problem 1.56P
Consider the compounds and ions with curved arrows drawn below. When the curved arrows give a second valid resonance structure, draw the resonance structure. When the curved arrows generate an invalid Lewis structure, explain why the structure is unacceptable.
a. 
b. 
c. 
d. 
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Consider the compounds and ions with curved arrows drawn below. When the curved arrows give a second valid resonance structure, draw the resonance structure. When the curved arrows generate an invalid Lewis structure, explain why the structure is unacceptable.
1. Consider the structure shown below and then answer the following questions.
a. Complete the structure by adding the missing formal charges. All atoms and lone pairs
are explicitly shown. (Hint: Consider the number of bonds neutral atoms have.)
:Ö:
H
‚H
H
H
b. Draw two more resonance structures of the molecule from part a by adding the missing î
bonds, lone pairs, and formal charges. All atoms in both structures should possess an
octet. (All atoms and o bonds are drawn for you; remember, only lone pairs and bonds
move in resonance structures.) Additional guidelines are given for each structure.
All atoms in this structure will be neutral (no
formal charges).
One oxygen atom has a +1 formal charge and
one oxygen atom has a -1 formal charge.
H
H
H
H
H
H
H
H
H
Draw a Lewis structure for BF3 that obeys the octet rule if possible and answer the following questions based on your drawing.
1. For the central boron atom:
- The number of lone pairs = ?
- The number of single bonds = ?
- The number of double bonds = ?
2. The central boron atom is
a. obeys the octet rule.
b. has an incomplete octet.
c. has an expanded octet.
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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- 1. Draw the resonance structures of the following molecule, using curved arrows to show electron movement and appropriate arrows to show the relationship between the structures. All lone pairs and charges must be clearly shown.arrow_forwardPart II Resonance 4. Draw all reasonable resonance structures for the following compound. Include only structures where all atoms (except H) have octets. Circle the most important structure that you drew. NH₂arrow_forwardValues if needec Draw (on paper) a Lewis structure for XeOF4 and answer the following questions based on your drawing. 1. For the central xenon atom: The number of lone pairs The number of single bonds = The number of double bonds = 2. The central xenon atom A. obeys the octet rule. B. has an incomplete octet. C. has an expanded octet. Submit Answer 5 question attempts remainingarrow_forward
- Draw three resonance structures, including non-bonding electrons.arrow_forwardEach compound contains both ions and covalent bonds. Draw the Lewis structure for compound. Show with dashes which are covalent bonds and show with charges which are ions. Q.Sodium methoxide, CH3ONaarrow_forwardDraw the resonance structures for the molecule, and rank the structures. (There should be four other structures). Keep in mind the rules for drawing and ranking resonance structures! ***Note, I have only drawn one. It is difficult for me to figure out what the other three are. Thank youarrow_forward
- Which of the following best describes electronegativity trends in the periodic table? I. Electronegativity inreases from right to left across a period. II. Electronegativity inreases from left to right across a period. III. Electronegativity inreases from bottom to top within a group. IV. Electronegativity inreases from top to bottom within a group. Select one: O a. I and IlI b. I and IV c. Il and III d. Il and IV e. None of these.arrow_forwardGive detailed Solution with explanation neededarrow_forwardCreate a second resonance structure. Include lone pairs and charges.arrow_forward
- For the following partial Lewis structure, which of the structures below (a-d) represent a valid resonance structure? *Hint - it may help you to complete the Lewis structure by drawing in all lone pairs. *Hint #2, this compound is neutral. H. a C d. N. H. b and d a d. Z-I Z-I +N-Harrow_forwardShow how these elements combine into octet-rule ionic compounds, as in the first example. First, draw atomic Lewis structures for the atoms and their O.R. ions. Show their charges, and use them to find the unit formula, and the name. Then draw atomic Lewis structures for all atoms in the formula unit together, show with arrows how all e¯s are transferred to make the ions, and draw the Lewis structure of the ionic compound. Atoms O.R. ions Unit formula Lewis Structure Name Transfer e¯s with arrows Mg + Br Magnesium bromide Li + C Lithium carbide Ge + Sarrow_forwardShow how these elements combine into octet-rule ionic compounds, as in the first example. First, draw atomic Lewis structures for the atoms and their O.R. ions. Show their charges, and use them to find the unit formula, and the name. Then draw atomic Lewis structures for all atoms in the formula unit together, show with arrows how all e s are transferred to make the ions, and draw the Lewis structure of the ionic compound. Unit formula Atoms O.R. ions Name Transfer e s with arrows Lewis Structure LizN le 1e 30 Lithium Li. + •N• Li. •N• Li. Li 30 Li Li Li :N: nitride )le Li. Pb and K and Harrow_forward
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