Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Question
Chapter 1, Problem 1.85P
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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Use the observed bond lengths to answer each question. (a) Why is bond [1] longer than bond [2] (143 pm versus 136 pm)? (b) Why are bonds [3] and [4] equal in length (127 pm), and shorter than bond [2]?
(a) Draw a second resonance structure for A. (b) Why can't a second resonance structure be drawn for B?
Which of the following Lewis dot structures is a valid Lewis structure?
H
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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 - Draw Lewis structures for each molecular formula....Ch. 1 - Prob. 1.9PCh. 1 - Prob. 1.10P
Ch. 1 - Prob. 1.11PCh. 1 - Prob. 1.12PCh. 1 - Draw a second resonance structure for each...Ch. 1 - Prob. 1.14PCh. 1 - Draw a second resonance structure for nitrous...Ch. 1 - Prob. 1.16PCh. 1 - Prob. 1.17PCh. 1 - Prob. 1.18PCh. 1 - Prob. 1.19PCh. 1 - Prob. 1.20PCh. 1 - Simplify each condensed structure by using...Ch. 1 - Prob. 1.22PCh. 1 - Prob. 1.23PCh. 1 - Convert each skeletal structure to a complete...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 - Classify each bond in the following molecules as ...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 - Two radioactive isotopes of iodine used for the...Ch. 1 - Prob. 1.40PCh. 1 - Assign formal charges to each carbon atom in the...Ch. 1 - Assign formal charges to each N and O atom in the...Ch. 1 - Draw one valid Lewis structure for each compound....Ch. 1 - Prob. 1.44PCh. 1 - Prob. 1.45PCh. 1 - Prob. 1.46PCh. 1 - Draw all possible isomers for each molecular...Ch. 1 - 1.45 Draw Lewis structures for the nine isomers...Ch. 1 - Prob. 1.49PCh. 1 - Prob. 1.50PCh. 1 - Prob. 1.51PCh. 1 - Prob. 1.52PCh. 1 - Prob. 1.53PCh. 1 - Prob. 1.54PCh. 1 - Draw all reasonable resonance structures for each...Ch. 1 - Prob. 1.56PCh. 1 - Rank the resonance structures in each group in...Ch. 1 - 1.56 Consider the compounds and ions with curved...Ch. 1 - 1.57 Predict all bond angles in each...Ch. 1 - Predict the geometry around each indicated atom....Ch. 1 - Prob. 1.61PCh. 1 - Prob. 1.62PCh. 1 - Draw in all the carbon and hydrogen atoms in each...Ch. 1 - Prob. 1.64PCh. 1 - Prob. 1.65PCh. 1 - Prob. 1.66PCh. 1 - Prob. 1.67PCh. 1 - Each of the following condensed or skeletal...Ch. 1 - Prob. 1.69PCh. 1 - Prob. 1.70PCh. 1 - Prob. 1.71PCh. 1 - Prob. 1.72PCh. 1 - Prob. 1.73PCh. 1 - Prob. 1.74PCh. 1 - Two useful organic compounds that contain Cl atoms...Ch. 1 - Use the symbols + and to indicate the polarity of...Ch. 1 - Label the polar bonds in each molecule. Indicate...Ch. 1 - Answer the following questions about acetonitrile...Ch. 1 - Prob. 1.79PCh. 1 - The principles of this chapter can be applied to...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. 1.85PCh. 1 - Prob. 1.86PCh. 1 - Prob. 1.87PCh. 1 - Prob. 1.88PCh. 1 - Prob. 1.89PCh. 1 - Prob. 1.90P
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- The cyanate ion is an anion consisting of one oxygen atom, one carbon atom, and onenitrogen atom, [OCN], in that order. a) Write three (3) resonance contributing structures for the cyanate ion. Show formalcharges.b) Based on your contributing structures, predict the O-C-N bond angle.arrow_forward12. 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-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_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_forward5. (i) Draw a complete Lewis dot structure for each of the following compounds. Clearly (ii) indicate all bonds and lone electrons, as well as the formal charge of each atom in the compound. a) NO3 b) NH4* c) CO2arrow_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
- Draw the shapes of the following molecules and ions in 3-dimension. Show clearly any lone pairs of electrons on the central atom, state the number of bond pairs and lone pairs of electrons on the central atom and name the shape of the molecule or ion. (a) SiCI4, silicon tetrachloride (b) PBr3, phosphorus tribromide (c) CI2O, dichlorine oxide Provide everything stated in the instructions for each compound.arrow_forwardDraw Lewis structures and any contributing resonance structures for each structure below. Use the proper type of arrow to indicate that they are resonance structures. In which structure is resonance more important? (a) H2SO3 (b) (HSO3)^1- (c) (SO3)^2-arrow_forward3.) 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_forward
- Which of the following species is a valid resonance structure of A? Usecurved arrows to show how A is converted to any valid resonancestructure. When a compound is not a valid resonance structure of A,explain why not.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_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_forward
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