Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 5, Problem 35CTQ
Interpretation Introduction
Interpretation: Any one structure from top row is enough to describe the molecule in top row but all structure is needed from bottom row to describe the molecule in bottom row should be explained.
Concept introduction: When one single structure is unable to describe all the properties of single molecule, a phenomenon called resonance comes into play. This arises when two or more than two Lewis structures are possible for one molecule. All such structures are called resonating structures and have same placement of atoms in them but these have different locations of bond pairs and lone pairs. The resonating structures are inter-convertible with each other. The resultant of all the resonating or contributing structures is called the resonance hybrid.
Rules to form resonance structure are as follows:
1. Use arrow types 1 and 2 for resonance structure of anions in movement of negative charge.
2. Use only arrow type 3 to move a positive charge for resonance structure of cations.
3. The sigma bond should not be broken. Any atom must not move from its place and total number of electrons must be same in all resonance structures.
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What are fuctional groups, are they only attached to carbon molecules or molecules that don't contain carbon?
A resonance hybrid is a structure that can be depicted by more than one valid Lewis structure.
part1: Draw the major resonance form of fulminic acid, HCNO, with the atoms connected as indicated in the formula. Your structure should have nonzero formal charges minimized, and it should include all nonzero formal charges and all nonbonding electrons.
part2: Draw the second most important resonance form of fulminic acid, HCNO, with the atoms connected as indicated in the formula. Your structure should have nonzero formal charges minimized, and it should include all nonzero formal charges and all nonbonding electrons.
part3: Draw the least important resonance contributor for fulminic acid, HCNO, with the atoms connected as indicated in the formula. Your structure should have nonzero formal charges minimized and should include all nonzero formal charges and all nonbonding electrons.
In the following Lewis structure of [SiF6]², every atom, bond and lone pair is positioned. To complete the structure, drag the formal
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zero, do not drag a tag to it.
When you drag the marker in, place the little crosshairs in the upper left corner of the marker directly over the atom(s) in
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:F:
:F
:
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Chapter 5 Solutions
Organic Chemistry: A Guided Inquiry
Ch. 5 - Which elements on the periodic table (other than...Ch. 5 - You will not find “hydroxide” in the stockroom,...Ch. 5 - Prob. 3CTQCh. 5 - Prob. 4CTQCh. 5 - Prob. 5CTQCh. 5 - Prob. 6CTQCh. 5 - On which do you expect to have a more intense and...Ch. 5 - Prob. 8CTQCh. 5 - Prob. 9CTQCh. 5 - Prob. 10CTQ
Ch. 5 - Prob. 11CTQCh. 5 - Prob. 12CTQCh. 5 - Prob. 13CTQCh. 5 - Prob. 14CTQCh. 5 - Prob. 15CTQCh. 5 - Prob. 16CTQCh. 5 - For each proposed set of resonance structures: a....Ch. 5 - Consider the polarization of the C=O bond in the...Ch. 5 - The C=O double bond is called a “carbonyl bond.”...Ch. 5 - Prob. 20CTQCh. 5 - Prob. 21CTQCh. 5 - Prob. 22CTQCh. 5 - Prob. 23CTQCh. 5 - Prob. 24CTQCh. 5 - Prob. 25CTQCh. 5 - Prob. 26CTQCh. 5 - Prob. 27CTQCh. 5 - Prob. 28CTQCh. 5 - Prob. 29CTQCh. 5 - Prob. 30CTQCh. 5 - Prob. 31CTQCh. 5 - Confirm that there is no legitimate Lewis...Ch. 5 - Draw all resonance structures of the molecule...Ch. 5 - Prob. 34CTQCh. 5 - Prob. 35CTQCh. 5 - Prob. 36CTQCh. 5 - Occasionally, we will see an ionic compound that...Ch. 5 - Prob. 2ECh. 5 - Prob. 3ECh. 5 - Prob. 4ECh. 5 - Is it possible to draw a resonance structure of...Ch. 5 - Prob. 6ECh. 5 - Prob. 7ECh. 5 - Prob. 8ECh. 5 - Phenol (shown below) has a pKa10 . a. Based on pKa...Ch. 5 - Use curved arrows to show the most likely...Ch. 5 - Prob. 12ECh. 5 - Complete each Lewis structure, draw all important...Ch. 5 - Use curved arrows to show the most likely...Ch. 5 - Construct an explanation for why sulfuric acid is...Ch. 5 - Prob. 16ECh. 5 - Prob. 17ECh. 5 - Prob. 18E
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- Consider the compound with the following condensed molecular formula: CH3CHOHCH=CH₂ What is the formal charge on the carbon atoms that only have single bonds? Formal charge: + What is the formal charge on the carbon atoms that have a double bond? Formal charge: + What is the formal charge on the oxygen atom? Formal charge: + What is the formal charge on the hydrogen atoms? Formal charge:arrow_forwardDraw a Lewis structure of your choice that has at least three equally reasonable resonance structures. You must show your work as to how the structure was drawn including showing valence electrons, any structures you draw that don’t work and require you to show a multiple bond, and formal charges on each atom that has a formal charge. For example, Nitrate ion has three structures (but you can’t draw this one). All three structures have formal charges and no one structure is preferred based on formal charge. Carbon dioxide would not be a valid choice. While it does have three structures, the structure that has two double bonds is the preferred structure while the structures with triple bonds are not equivalent to the double bonded version as they have multiple formal charges present.arrow_forwardDraw a complete Lewis structure for histidine in which all atoms have a formal charge of zero.arrow_forward
- Two major resonance structures are possible for the anion shown. One resonance form is given, but it is incomplete. Complete the given structure by adding nonbonding electrons and formal charges. Draw the remaining structure, including nonbonding electrons and formal charges. Omit curved arrows. Structure A: complete the structure by adding nonbonding electrons and formal charges. H H H I Structure B: draw the remaining resonance structure, including nonbonding electrons and formal charges. H- : z: H Harrow_forwardHow do you know when to draw a solid wedge vs a dashed wedge when drawing 3D bond-line structures? I know that solid-wedge means the atom is pointing towards you and dashed wedge means it's in the back, but how do you know which atoms are in the front as opposed to the back? How can you tell what the configuration will look like in space just by looking at the lewis structure or name?arrow_forwardChemistry (a) Write three more resonance structures for each of compounds 1 and 2. (b) In each of compounds 1 and 2, determine which resonance structure contributes the most and explain your answer. (c) Are the 3/4 structures resonance structures or different compounds? Same question for 5/6 structures. Explain your answers.arrow_forward
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- Three major contributing resonance structures are possible for the following cation. One is given below. Draw the remaining structures (in any order), including nonbonding electrons and formal charges. Omit curved arrows. н н CH3З Which contributes most to the hybrid? The structure with the positive charge on sulfur. All contribute equally. O The structures with the positive charge on carbon.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
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