Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 1, Problem 1.58P
Interpretation Introduction
Interpretation:
All resonance structures of the given pair of structurally similar ionic species are to be drawn and the more stable of the two is to be determined.
Concept introduction:
Resonance leads to stabilization of a compound. More the number of resonance structures, higher the stability of the compound.
Lower the number of atoms with formal charges in the resonance structure of a species, the more stable it is.
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The two species shown are structurally very similar. Draw all resonance structures for each species and
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Compare with explanation the acidity of the following pairs of compounds.
(Note: You must draw the appropriate resonance structures to support your
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(c)
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Draw all resonance contributors for each of the following molecules or ions. Be sure to include the curved arrows thatindicate which pairs of electrons are shifted in going from one resonance structure to the next.(a) CH3NO2(b) CH3CO-2(c) CH3CHCHCH-2(the ion has two C-C single bonds)(d) C5H5N (a ring is formed by the C and N atoms, and each H is bonded to C)(e) C4H5N (a ring is formed by the C and N atoms, the N is bonded to one H, and each C is bonded to one H)
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
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- The curved arrow notation introduced in Section 1.6B is a powerful method used by organic chemists to show the movement of electrons not only in resonance structures, but also in chemical reactions.Because each curved arrow shows the movement of two electrons, following the curved arrows illustrates what bonds are broken and formed in a reaction. Consider the following three-step process. (a) Add curved arrows in Step [1] to show the movement of electrons. (b) Use the curved arrows drawn in Step [2] to identify the structure of X. X is converted in Step [3] to phenol and HCl.arrow_forward4. (i) On the structure below, add all missing lone pairs of electrons, assuming that all of the formal charges are correct. (ii) Draw line-angle structures for all resonance forms (including minor, but still significant) using appropriate notation, including double-headed resonance arrows and curved arrows for electrons. (Hint: Draw two more) (iii) Rank the three structures from most =1 to least =3 important.arrow_forwardFor each of the following structures,1. Draw a Lewis structure; fill in any nonbonding electrons.2. Calculate the formal charge on each atom other than hydrogen.(a) CH3NO(nitromethane)(b) (CH3)3NO(trimethylamine oxide)(c) [N3]-(azide ion)(d) [(CH3)3O]+ (e) CH3NC (f) (CH3)4NBrarrow_forward
- The curved arrow notation introduced in Section 1.6B is a powerfulmethod used by organic chemists to show the movement of electronsnot only in resonance structures, but also in chemical reactions.Because each curved arrow shows the movement of two electrons,following the curved arrows illustrates what bonds are broken andformed in a reaction. Consider the following three-step process. (a) Addcurved arrows in Step [1] to show the movement of electrons. (b) Use thecurved arrows drawn in Step [2] to identify the structure of X. X isconverted in Step [3] to phenol and HCl.arrow_forwardDraw a structural formula for a hydrocarbon with the given molecular formula that undergoes hydroboration-oxidation to give the indicated product. (a) (b) • All hydrogen atoms are implied. Apply formal charges where appropriate. • Omit lone pairs and radical electrons from your answer. ● C₂H10 C₂H12 1. (sia) BH 2. H₂O₂, NaOH MAVIL / 1. BHs 2. H₂O₂, NaOH Η OO Sn [F ? ChemDoodle OH Sn [F ? Previous Nextarrow_forward(a) Draw the major resonance forms of each of these ions. Pcaetre gol2 (b) Circle the most stable of the two ions in part a.arrow_forward
- Determine the weakest C-H bond in each of the following compounds. (a) (b) (c) ОНarrow_forwardThe curved arrow notation introduced in Section 1.6 is a powerful method used by organic chemists to show the movement of electrons not only in resonance structures, but also in chemical reactions. Since each curved arrow shows the movement of two electrons, following the curved arrows illustrates what bonds are broken and formed in a reaction. Consider the following three-step process. (a) Add curved arrows in Step [1] to show the movement of electrons. (b) Use the curved arrows drawn in Step [2] to identify the structure of X. X is converted in Step [3] to phenol and HCl.arrow_forwardHydrocarbon A possesses a significant dipole, even though it is composed of only C—C and C—H bonds. Explain why the dipole arises and use resonance structures to illustrate the direction of the dipole. Which ring is more electron rich?arrow_forward
- QUESTION 4. (a) Below are two structural isomers. Interestingly, one of these structures is significantly more acidic than the other. Circle the most acidic proton in each. Determine which structure is more acidic and explain why. Use your knowledge of resonance structures and molecular geometry to support your argument. NO₂ NO₂ OH OHarrow_forwardDraw a structural formula for a hydrocarbon with the given molecular formula that undergoes hydroboration-oxidation to give the indicated product. (a) (b) • All hydrogen atoms are implied. Apply formal charges where appropriate. • Omit lone pairs and radical electrons from your answer. ● C₂H10 C₂H12 1. (sia) BH 2. H₂O₂, NaOH Il 1. BH₂ 2. H₂O2₂, NaOH H Sn [F ? ChemDoodle OHarrow_forward1. Draw Lewis structures for the following compounds. Remember to enclose ions in square brackets. On your answer sheet, state the number of valence electrons in each compound. (a) Na₂S (b) (CH3)₂S (c) KOCI List the most important (etrongnet) inarrow_forward
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