Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 1, Problem 1.12YT
Interpretation Introduction
Interpretation:
To supply necessary curved arrow(s) to convert the resonance structure on the left into the one on the right.
Concept introduction:
In the two species, the bonds are delocalized. This delocalization of bonds in species can be explained using the resonance concept. Resonance exists in species for which there are two or more valid Lewis structures. For such species, each valid Lewis structure is called a resonance structure or a resonance contributor. The delocalization is shown using curved arrows.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Draw a resonance structure of the compound shown below, called 2-heptanone, which is found in some kinds of cheese.
en
Draw curved arrow(s) on the initial structure to show the expected resonance. Modify the second structure given to draw a new
resonance structure, including any relevant formal charges. Use the + and - tools to add/remove charges to an atom, and use the single
bond tool to add/remove double bonds.
H3C
CH3
Edit Drawing
H3C
CH3
Follow the curved arrows and draw a Lewis structure for the resulting resonance contributor of azide ion, adding charges and lone electron pairs to the appropriate atoms.
=N=N:
+
Explicitly draw all H atoms.
• Include all valence lone pairs in your answer.
opy
aste
Shown below is the major resonance structure for a molecule. Draw the second best resonance structure of the molecule. Include all non-zero formal
charges.
H-N-C =C-H
Click and drag to
start drawing a
structure.
1
Chapter 1 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
Ch. 1 - Prob. 1.1PCh. 1 - Prob. 1.2PCh. 1 - Prob. 1.3PCh. 1 - Prob. 1.4PCh. 1 - Prob. 1.5PCh. 1 - Prob. 1.6PCh. 1 - Prob. 1.7PCh. 1 - Prob. 1.8PCh. 1 - Prob. 1.9PCh. 1 - Prob. 1.10P
Ch. 1 - Prob. 1.11PCh. 1 - Prob. 1.12PCh. 1 - Prob. 1.13PCh. 1 - Prob. 1.14PCh. 1 - Prob. 1.15PCh. 1 - Prob. 1.16PCh. 1 - Prob. 1.17PCh. 1 - Prob. 1.18PCh. 1 - Prob. 1.19PCh. 1 - Prob. 1.20PCh. 1 - Prob. 1.21PCh. 1 - Prob. 1.22PCh. 1 - Prob. 1.23PCh. 1 - Prob. 1.24PCh. 1 - Prob. 1.25PCh. 1 - Prob. 1.26PCh. 1 - Prob. 1.27PCh. 1 - Prob. 1.28PCh. 1 - Prob. 1.29PCh. 1 - Prob. 1.30PCh. 1 - Prob. 1.31PCh. 1 - Prob. 1.32PCh. 1 - Prob. 1.33PCh. 1 - Prob. 1.34PCh. 1 - Prob. 1.35PCh. 1 - Prob. 1.36PCh. 1 - Prob. 1.37PCh. 1 - Prob. 1.38PCh. 1 - Prob. 1.39PCh. 1 - Prob. 1.40PCh. 1 - Prob. 1.41PCh. 1 - Prob. 1.42PCh. 1 - Prob. 1.43PCh. 1 - Prob. 1.44PCh. 1 - Prob. 1.45PCh. 1 - Prob. 1.46PCh. 1 - Prob. 1.47PCh. 1 - Prob. 1.48PCh. 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 - Prob. 1.55PCh. 1 - Prob. 1.56PCh. 1 - Prob. 1.57PCh. 1 - Prob. 1.58PCh. 1 - Prob. 1.59PCh. 1 - Prob. 1.60PCh. 1 - Prob. 1.61PCh. 1 - Prob. 1.62PCh. 1 - Prob. 1.63PCh. 1 - Prob. 1.64PCh. 1 - Prob. 1.65PCh. 1 - Prob. 1.66PCh. 1 - Prob. 1.67PCh. 1 - Prob. 1.68PCh. 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 - Prob. 1.75PCh. 1 - Prob. 1.76PCh. 1 - Prob. 1.77PCh. 1 - Prob. 1.78PCh. 1 - Prob. 1.79PCh. 1 - Prob. 1.80PCh. 1 - Prob. 1.81PCh. 1 - Prob. 1.82PCh. 1 - Prob. 1.1YTCh. 1 - Prob. 1.2YTCh. 1 - Prob. 1.3YTCh. 1 - Prob. 1.4YTCh. 1 - Prob. 1.5YTCh. 1 - Prob. 1.6YTCh. 1 - Prob. 1.7YTCh. 1 - Prob. 1.8YTCh. 1 - Prob. 1.9YTCh. 1 - Prob. 1.10YTCh. 1 - Prob. 1.11YTCh. 1 - Prob. 1.12YTCh. 1 - Prob. 1.13YTCh. 1 - Prob. 1.14YTCh. 1 - Prob. 1.15YTCh. 1 - Prob. 1.16YTCh. 1 - Prob. 1.17YT
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Follow the curved arrows and draw a Lewis structure for the resulting resonance contributor of 1,3-butadiene, adding charges and lone electron pairs to the appropriate atoms. CH2arrow_forwardA. в. с. Figure 4-8 D. СН3 0: сн. H cle 2 СН3 СН3 - н CH2 ва Бе СН3 fo: H Le :CH₂ CH 3 того CH Снзarrow_forwardComplete the Lewis structure for each of the following molecules using the information proVided in lable 1-4. You may assume that all formal charges are zero. All H atoms are shown; add only bonding pairs and lone pairs of electrons. (a) (b) нн H (c) N- H-C-Ć-C-N-0 н н H. N.arrow_forward
- Diazomethane has the formula H2CN2. Draw all valid resonance contributors for diazomethane and, using Table 1-3, propose which one contributes more to the resonance hybrid. Hint: There are no structures that avoid charged atoms.arrow_forwardThree resonance structures are possible for the structure shown. One resonance form is given. Draw the remaining resonance structures, in any order, including nonbonding electrons. Omit curved arrows. H H H Harrow_forwardUsing π electrons and/or lone pairs in the following conjugated system, create a resonance form by moving electrons as far as possible. Be sure to include all lone pairs and charges. Part: 0 / 2 Part 1 of 2 Add curved arrow notation to show how electrons will move to form a different resonance form. + -NEN: X :0 O m FE 21 5 Uarrow_forward
- Which of the highlighted chemical bonds in the molecules below is longest? Shortest? In between? Which highlighted bond requires the highest energy to break? Lowest? In between? Answer these questions by completing the second and third columns in the table. compound H H | | H-C=C -0- - H H-C=C-O-H H H | | H-C-C-0-H I I H H length of highlighted bond choose one - choose one - v choose one energy of highlighted bond choose one - choose one choose onearrow_forward3-31 Why does electronegativity generally increase going from left to right across a row of the Periodic Table?arrow_forwardThe following model is a representation of citric acid, the key substance in the so-called citric acid cycle, by which food molecules are metabolized in the body. Only the connections between atoms are shown; multiple bonds are not indicated. Complete the structure by indicating the positions of multiple bonds and lone-pair electrons (gray = C, red = O, ivory = H).arrow_forward
- Which of the highlighted chemical bonds in the molecules below is longest? Shortest? In between? Which highlighted bond requires the highest energy to break? Lowest? In between? Answer these questions by completing the second and third columns in the table. compound HI H -Si-H | H H | H-Ge-H | H HICIH Η HIC-H Η length of highlighted bond choose one choose one choose one - V - V energy of highlighted bond choose one - choose one - choose one - ✓ X Śarrow_forwardFollow the curved arrows and draw a Lewis structure for the resulting resonance contributor of azide ion, adding charges and lone electron pairs to the appropriate atoms. :N=N=N: ? • Explicitly draw all H atoms. • Include all valence lone pairs in your answer.arrow_forwardWhich of the highlighted chemical bonds in the molecules below is longest? Shortest? In between? Which highlighted bond requires the highest energy to break? Lowest? In between? Answer these questions by completing the second and third columns in the table. compound H HICIO | H :C=0: :0: || H-C-H H length of highlighted bond choose one choose one - V choose one - ✓ energy of highlighted bond choose one choose one choose one X Śarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning