ORGANIC CHEMISTRY SG/SM PA +SQUARECAP E
2nd Edition
ISBN: 9780393434064
Author: KARTY
Publisher: NORTON
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Question
Chapter 14, Problem 14.4YT
Interpretation Introduction
Interpretation:
The fraction of an average
Concept introduction:
The resonance energy of benzene is
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Which of the following species (B, C,D) is a valid resonance of A?
Use curved arrows to show how A is converted to any valid resonance structure.
3. Which of the following molecules are conjugated? For those which are conjugated, write a resonance
structure.
T
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
HO
Chapter 14 Solutions
ORGANIC CHEMISTRY SG/SM PA +SQUARECAP E
Ch. 14 - Prob. 14.1PCh. 14 - Prob. 14.2PCh. 14 - Prob. 14.3PCh. 14 - Prob. 14.4PCh. 14 - Prob. 14.5PCh. 14 - Prob. 14.6PCh. 14 - Prob. 14.7PCh. 14 - Prob. 14.8PCh. 14 - Prob. 14.9PCh. 14 - Prob. 14.10P
Ch. 14 - Prob. 14.11PCh. 14 - Prob. 14.12PCh. 14 - Prob. 14.13PCh. 14 - Prob. 14.14PCh. 14 - Prob. 14.15PCh. 14 - Prob. 14.16PCh. 14 - Prob. 14.17PCh. 14 - Prob. 14.18PCh. 14 - Prob. 14.19PCh. 14 - Prob. 14.20PCh. 14 - Prob. 14.21PCh. 14 - Prob. 14.22PCh. 14 - Prob. 14.23PCh. 14 - Prob. 14.24PCh. 14 - Prob. 14.25PCh. 14 - Prob. 14.26PCh. 14 - Prob. 14.27PCh. 14 - Prob. 14.28PCh. 14 - Prob. 14.29PCh. 14 - Prob. 14.30PCh. 14 - Prob. 14.31PCh. 14 - Prob. 14.32PCh. 14 - Prob. 14.33PCh. 14 - Prob. 14.34PCh. 14 - Prob. 14.35PCh. 14 - Prob. 14.36PCh. 14 - Prob. 14.37PCh. 14 - Prob. 14.38PCh. 14 - Prob. 14.39PCh. 14 - Prob. 14.40PCh. 14 - Prob. 14.41PCh. 14 - Prob. 14.42PCh. 14 - Prob. 14.43PCh. 14 - Prob. 14.44PCh. 14 - Prob. 14.45PCh. 14 - Prob. 14.46PCh. 14 - Prob. 14.47PCh. 14 - Prob. 14.48PCh. 14 - Prob. 14.49PCh. 14 - Prob. 14.50PCh. 14 - Prob. 14.51PCh. 14 - Prob. 14.52PCh. 14 - Prob. 14.53PCh. 14 - Prob. 14.54PCh. 14 - Prob. 14.55PCh. 14 - Prob. 14.56PCh. 14 - Prob. 14.57PCh. 14 - Prob. 14.58PCh. 14 - Prob. 14.59PCh. 14 - Prob. 14.60PCh. 14 - Prob. 14.61PCh. 14 - Prob. 14.62PCh. 14 - Prob. 14.63PCh. 14 - Prob. 14.64PCh. 14 - Prob. 14.65PCh. 14 - Prob. 14.66PCh. 14 - Prob. 14.1YTCh. 14 - Prob. 14.2YTCh. 14 - Prob. 14.3YTCh. 14 - Prob. 14.4YTCh. 14 - Prob. 14.5YTCh. 14 - Prob. 14.6YTCh. 14 - Prob. 14.7YTCh. 14 - Prob. 14.8YTCh. 14 - Prob. 14.9YTCh. 14 - Prob. 14.10YTCh. 14 - Prob. 14.11YTCh. 14 - Prob. 14.12YTCh. 14 - Prob. 14.13YT
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- Which of the following species is a valid resonance structure of A? Use curved arrows to show how A is converted to any valid resonance structure. When a compound is not a valid resonance structure of A, explain why not.arrow_forwardBelow is the SN2 reaction between iodocyclohexane and cyanide (CN–). Draw the missing curved arrow notation in the first box to reflect electron movements. In both boxes, add lone pairs of electrons and nonzero formal charges.arrow_forwardUne or more valid answers. Explain the answers. The localization or resonance energy: a) Justify the increased stability of molecules that have unlocated electrons b) It is a consequence of the mobility of the electrons that form the “sigma” bonds c) It occurs in compounds with conjugated double bonds, but not in aromatic compounds d) It is shown by the experimental values of the enthalpies of formation.arrow_forward
- In the following Lewis structure of [BrO3]", every atom, bond and lone pair is positioned. To complete the structure, drag the formal charge tags to the appropriate atom(s). Each marker may be used more than once, or not at all. If an atom has a formal charge of 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 question (not above them). Ö: Br: 2+ 2-arrow_forward10. Draw 2 valid resonance structures for each of the following molecule. a) b) c) : ZI H :0: :0: u N: the overall bybarrow_forwardI am having trouble on part c. It wants me to draw the resonance structure, but in mastering chem there’s no arrows available for some reason . Is there a way to draw it without the arrows and still be resonancearrow_forward
- Describe with words how you would draw the curved arrow(s) to get to the more stable resonance form for the left-hand pair. Be sure to include how many curved arrows are needed and what atom (or bond) the electrons are coming from or going to. Do the same for the resonance pair on the right-hand side. more stable more stablearrow_forwardThe resonance structures shown below have all lone pairs drawn in, but are missing formal charges. Hint: the overall charge on the molecule is +1. What is the formal charge on the carbon labelled (A)? What is the formal charge on the nitrogen labelled (B)? What is the formal charge on the carbon labelled (C)? What is the formal charge on the nitrogen labelled (D)? Please state your answer with a "+" or "-" sign followed by a number. For 0, just write "0". HC DH A B H. C-N C=N. H. H. H. Harrow_forwardFor the structure shown in the box below identify two corresponding correct resonance structures.arrow_forward
- O REPRESENTATIONS OF ORGANIC MOLECULES Ranking resonance structures Rank the resonance structures in each row of the table from major to minor. For example, in the first row, select (major) for the major resonance contributor. If two or more structures in the same row contribute equally, rank them equally by selecting the same number. H. H H. H. H. H. H. H. (Rank) (Rank) (Rank) H. H. H. H. H. H. H. (Rank) (Rank) :o: Rank) (Rank) 74°F DELL F5 F6 F7 F8 F9 F10 F11 PrtScr F12 24arrow_forwardDraw a reasonable resonance structure for the following species. Draw out all bonds to the oxygen atom in your answer.arrow_forwardThe 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_forward
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