ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Question
Chapter 1, Problem 1.80P
Interpretation Introduction
(a)
Interpretation: The reason for difference in bond lengths of the bond [1] and bond [2] is to be stated.
Concept introduction: With an increase in the
Interpretation Introduction
(b)
Interpretation: The reason for equal bond length of bonds [3] and [4] and shorter bond length than bond [2] is to be stated.
Concept introduction: Resonance plays a significant role in stabililizing the molecule and it is responsible for properties exhibited by the molecule.
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3. (a) Draw a resonance structure for Molecule 1 in Box B, which satisfies the octet for all non-
hydrogen atoms. Hint you may want to use curved arrows to move electrons over the skeleton of
Molecule 3 to help you find the resonance structure.
H
H
H
H
Molecule 1
H
H
3. (b) Fill in the table below for Molecule 1
Box B: Resonance Structure of Molecule 1
VSEPR electron pair
geometry around
atom
Molecular geometry
Approximate bond
or shape around atom angles around atom
N atom
CH3 C atom
CH C atoms
3. (c) Given the information that resonating electrons are delocalized and so are not used to
determine VSEPR geometry, how will the table you filled in for 3.(b) change?
12. Draw 2 resonance structures for each of the following two molecules/ions. Make sure
you include formal charges on all atoms. Indicate which of the 2 resonance structures is
preferred. (a) N2O (b) SCN-
Which of the following Lewis dot structures is a valid Lewis structure?
H
+YF
H
H-P
None of these
: Si=
CI
are
H-
H.
plausible/valid.
H.
:F:
H
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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- Methyl isocyanate, CH3NCO, was made infamous in 1984when an accidental leakage of this compound from a storagetank in Bhopal, India, resulted in the deaths of about3800 people and severe and lasting injury to many thousandsmore. (a) Draw a Lewis structure for methyl isocyanate.(b) Draw a ball-and-stick model of the structure,including estimates of all the bond angles in the compound.(c) Predict all the bond distances in the molecule.(d) Do you predict that the molecule will have a dipolemoment? Explain.arrow_forward(a) Use a polar arrow to indicate the polarity of each bond: N¬H, F¬N, I¬Cl. (b) Rank the following bonds in order of increasing polarity and decreasing percent ionic character: H¬N, H¬O, H¬C.arrow_forward3) The molecule diphosphorus tetraoxide (P,O,) has two central atoms and four different resonance structures that do not violate the octet rule. Draw two of these resonance structures below. 4) The compound acetone is a common solvent. It has a chemical formula of CH,COCH, Acetone has three central atoms. (a) Draw the Lewis Dot structure for acetone. (b) Give the Ideal Bond Angle for all three central atoms. 5) Four covalent molecules are drawn below. :o: H. H-CH H H (1) (2) (3) (4) a) Define each of these molecules as polar or non-polar. (1) (2) (3) b) Describe the type of intermolecular force that each molecule would use: (1) (2) (3) (4)arrow_forward
- 3.) Draw the two possible Lewis structures for acetamide, H₂CCONH2. Calculate the formal charge on each atom in each structure and use formal charge to indicate the more likely structure. Label all bonds as being polar or nonpolar.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
- 5. For the reaction H2(g) + C2H4(g) C2H6(g) (a) Estimate the enthalpy of reaction, using the bond enthalpy values. (b) Calculate the enthalpy of reaction, using standard enthalpies of formation. (AH? for H2, C2H4, and C2H6 are 0 kJ/mol, 52.3 kJ/mol, and -84.7 kJ/mol, respectively.)arrow_forward1arrow_forward1.) What is the Lewis structure for the methylthiolate anion, CH3S-. Carbon is the central atom. Show any nonzero formal charges. 2.) Proteins are large molecules that affect almost every function of the human body. Proteins are composed of smaller building blocks called amino acids. The simplest amino acid is glycine. When dissolved in water, two atoms in a glycine molecule have a formal charge. In the lewis structure of glycine C2H5NO2 all bonds are drawn (image is provided), but the unbonded valence electrons (lone pairs) are missing. Copy the structure and draw the missing valence electrons (lone pairs). Locate the 2 atoms that have a nonzero formal charge. Calculate the charge at these sites.arrow_forward
- The two compounds nitrogen dioxide and dinitrogentetraoxide are introduced in Section 3.13.(a) NO2 is an odd-electron compound. Draw the bestLewis diagrams possible for it, recognizing that oneatom cannot achieve an octet configuration. Use formal charges to decide whether that should be the(central) nitrogen atom or one of the oxygen atoms.(b) Draw resonance forms for N2O4 that obey the octetrule. The two N atoms are bonded in this molecule.arrow_forwardDraw the most stable resonance structure for PO2Cl. Explain your reasoning for why this would be the most stable.arrow_forwardCalculate the enthalpy change for the following reactions using the bond enthalpy given below. (Bond enthalpy/kJ : H−H = 436, C−H = 413, C=O = 799, O=O = 495, O−H = 463) (a) H2(g) + 1⁄2O2(g) → H2O(g) (b) CH4(g) + 2O2(g) → CO2(g) + 2H2O(l)arrow_forward
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