Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 5, Problem 34CTQ
Interpretation Introduction
Interpretation: The important resonances of below molecules should be drawn.
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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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.
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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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- The C=O double bond is called a “carbonyl bond.” Acetone and othercarbonyl compounds are introduced in some texts along with this structure a. Is this an important resonance structure of acetone? Explain. b. Does this structure convey any useful information about acetone? If so, what?arrow_forwardCould you draw all valid resonance structrues for these two? I understand the rules for drawing resonance structures but I miss a lot of them.arrow_forward3. The following shows all resonance structures for the following molecule. a. Draw in all implied lone pairs. b. Draw in curved arrows that show the flow of electrons, making sure the arrows show the precise starting point and destination of the electrons. Label each arrow as: lp →→→л (p=lone pair) c. d. Rank the resonance structures from most stable to least based on the number of formal charges and atoms that lack an octet of electrons. ol-of-o. B A D d-d-d-o E C F Garrow_forward
- For the given compound, draw all significant resonance forms and rank them from most significant to least significant. Briefly explain the rankings. Part 1 Let's begin by considering which resonance patterns are present. First, add curved arrow(s) to show the resonance using the following pattern: a pi bond between two atoms of differing electronegativity. Modify the second structure given to draw the new resonance structure. Include relevant formal charges in your structure. Use the + and - tools to add/remove charges to an atom, and use the single bond tool to add/remove double bonds. H₂C CH₂ H₂C Edit Drawing CH₂ SUPPORTarrow_forwardT 1C2: Draw multiple, valid resonance structures for line-angle structures using curved arrow notation and rank drawn resonance structures in order of their energy, stability, and contribution to the overall electronic nature of the structure. Fill in the data table with regard to the resonance structures given. Be sure to show all your important work for credit on this problem. Structure- Data Redraw Original Structure and Add Lone Pairs Redraw Original Structure with Lone Pairs and Add Curved Arrows to Neutralize as Many Formal Charges as Possible Draw Resonanc Structure That Follows From Curved Arrows Drawn Above ... Which Resonance Structure is Lower Energy (Original or Yours)? Why? HOO O OO OH CH3 O ✪ OH ⒸOH HOarrow_forwardFollow the curved arrows to draw a second resonance structure for eachspecies.arrow_forward
- 2) (cont.) In the box below each Lewis drawing, PRINT one of the three following ABBREVIATIONS to characterize that Lewis drawing's relevance to the molecule's ACTUAL structure. i) CRS (Contributing Resonance Structure) ii) RS (Resonance Structure but not a CRS) iii) NRS (Not a Resonance Structure)arrow_forwarda) Draw the Lewis structure for the molecule on the left (labeled as Molecule A above). Draw the Lewis structure which has minimum formal charges. b) Draw the correct Lewis structure for the molecule on the right (labeled as Molecule B above). Draw the Lewis structure which has minimum formal charges. c) Select the three TRUE statements from those provided below. The molecule on the right (Molecule B) is planar (all atoms lie within the same plane). The molecule on the left (Molecule A) is planar (all atoms lie within the same plane). The molecule on the right (Molecule B) has polar bonds. The molecule on the left (Molecule A) has polar bonds. We can distinguish between the two molecules (Molecule A and Molecule B) based upon their dipole moment.arrow_forward2. Tetrahydrocannabinolic acid (THCA), the precursor to THC, a psvchoactive: H.. • This molecule is missing eight lone pairs. Add them to the structure above • Check the formal charges of the oxygen atoms above. Do any of them have a non-zero formal charge? If so, add the charges to the appropriate oxygen atoms • THCA is a weak acid. Identify and circle the acidic hydrogen on the above structure • Draw a resonance structure of this molecule belowarrow_forward
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