ORGANIC CHEMISTRY
6th Edition
ISBN: 9781260826791
Author: SMITH
Publisher: MCG
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Question
Chapter 1, Problem 83P
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]?
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?
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]?
Chapter 1 Solutions
ORGANIC CHEMISTRY
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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- 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-arrow_forwardThe 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_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_forward
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- 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_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_forward5. 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_forward
- 3. Consider the four compounds BB33, CB14, NB13, and Br,O. Use periodic trends in bond lengths and the electronegativity table in Chang to answer the following questions: (a) Which molecule is expected to have the longest bonds? (b) Which molecule is expected to have the most polar bonds? (c) Which molecule is expected to have the least polar bonds?arrow_forward2. Consider the following molecules or ions: H2O, SF4, IF4", and COF2. Answer the following questions based on the Lewis structures and VSEPR theory prediction of their molecular shapes. (a) Which one has only bond angles of 109.5°? (b) Which one has only bond angles of 120°? (c) Which one has bond angles of 90 and 180°? (d) Which one has bond angles of 90, 120, and 180°?arrow_forwardRank the following bonds in order of increasing bond length.arrow_forward
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