Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 2, Problem 2.20P
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Problem (#2.)
For each ion below, draw all reasonable resonance structures (linked by resonance arrows “↔”). Include curved arrows that indicate the movement of electrons between each resonance structure. Assign non-zero formal charges to each atom for each resonance structure.
(a.) NO3– (nitrate)
(b.) CH3COO– (acetate)
(c.) N3– (azide)
(d.) NCO– (isocyanate)
Problem (#3.)
For each ion in question 2, draw a resonance hybrid, assigning non-zero formal and/or partial charges (δ+, δ–) as needed.
Problem (#4.)
For each skeletal structure below, satisfy the valences (or octets) of all of the atoms by filling in double and triple bonds as well as unshared electron pairs. Assign non-zero formal charges and show the overall charge if the structure is an ion.
See photo attached for Problem number 4.
Problem (#5.)
For each structure in question 4, draw a resonance hybrid (if it has one) and assign non-zero formal and/or partial charges as needed.
(a) Draw all valid resonance contributors for this iIon. Show how the electrons can be moved using curved arrOWs.
(b) Draw the resonance hybrid.
Please draw the arrow formalism on the 1st structure (top) that accounts for the 2nd resonance structure (bottom).
Chapter 2 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
Ch. 2 - Prob. 2.1PCh. 2 - Prob. 2.2PCh. 2 - Prob. 2.3PCh. 2 - Prob. 2.4PCh. 2 - Prob. 2.5PCh. 2 - Prob. 2.6PCh. 2 - Prob. 2.7PCh. 2 - Prob. 2.8PCh. 2 - Prob. 2.9PCh. 2 - Prob. 2.10P
Ch. 2 - Prob. 2.11PCh. 2 - Prob. 2.12PCh. 2 - Prob. 2.13PCh. 2 - Prob. 2.14PCh. 2 - Prob. 2.15PCh. 2 - Prob. 2.16PCh. 2 - Prob. 2.17PCh. 2 - Prob. 2.18PCh. 2 - Prob. 2.19PCh. 2 - Prob. 2.20PCh. 2 - Prob. 2.21PCh. 2 - Prob. 2.22PCh. 2 - Prob. 2.23PCh. 2 - Prob. 2.24PCh. 2 - Prob. 2.25PCh. 2 - Prob. 2.26PCh. 2 - Prob. 2.27PCh. 2 - Prob. 2.28PCh. 2 - Prob. 2.29PCh. 2 - Prob. 2.30PCh. 2 - Prob. 2.31PCh. 2 - Prob. 2.32PCh. 2 - Prob. 2.33PCh. 2 - Prob. 2.34PCh. 2 - Prob. 2.35PCh. 2 - Prob. 2.36PCh. 2 - Prob. 2.37PCh. 2 - Prob. 2.38PCh. 2 - Prob. 2.39PCh. 2 - Prob. 2.40PCh. 2 - Prob. 2.41PCh. 2 - Prob. 2.42PCh. 2 - Prob. 2.43PCh. 2 - Prob. 2.44PCh. 2 - Prob. 2.45PCh. 2 - Prob. 2.46PCh. 2 - Prob. 2.47PCh. 2 - Prob. 2.48PCh. 2 - Prob. 2.49PCh. 2 - Prob. 2.50PCh. 2 - Prob. 2.51PCh. 2 - Prob. 2.52PCh. 2 - Prob. 2.53PCh. 2 - Prob. 2.54PCh. 2 - Prob. 2.55PCh. 2 - Prob. 2.56PCh. 2 - Prob. 2.57PCh. 2 - Prob. 2.58PCh. 2 - Prob. 2.59PCh. 2 - Prob. 2.60PCh. 2 - Prob. 2.61PCh. 2 - Prob. 2.62PCh. 2 - Prob. 2.63PCh. 2 - Prob. 2.64PCh. 2 - Prob. 2.65PCh. 2 - Prob. 2.66PCh. 2 - Prob. 2.67PCh. 2 - Prob. 2.68PCh. 2 - Prob. 2.69PCh. 2 - Prob. 2.70PCh. 2 - Prob. 2.71PCh. 2 - Prob. 2.72PCh. 2 - Prob. 2.1YTCh. 2 - Prob. 2.2YTCh. 2 - Prob. 2.3YTCh. 2 - Prob. 2.4YTCh. 2 - Prob. 2.5YTCh. 2 - Prob. 2.6YTCh. 2 - Prob. 2.7YTCh. 2 - Prob. 2.8YTCh. 2 - Prob. 2.9YTCh. 2 - Prob. 2.10YTCh. 2 - Prob. 2.11YTCh. 2 - Prob. 2.12YTCh. 2 - Prob. 2.13YTCh. 2 - Prob. 2.14YTCh. 2 - Prob. 2.15YTCh. 2 - Prob. 2.16YTCh. 2 - Prob. 2.17YTCh. 2 - Prob. 2.18YTCh. 2 - Prob. 2.19YTCh. 2 - Prob. 2.20YT
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- Please don't provide handwrittin solution....arrow_forwardDescribe 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_forwardSee image belowarrow_forward
- Curved arrows are used to illustrate the flow of electrons. Using the provided resonance structures, draw the curved electron-pushing arrows to show the interconversion between resonance hybrid contributors. Be sure to account for all bond- breaking and bond-making steps. Drawing Arrows RADA + Unda Reset Done Drag Taarrow_forwardSee image belowarrow_forwardx-xo B Draw molecule A. On that drawing include the lone pairs and the curved arrows that would produce resonance structure B.arrow_forward
- can you answer this again in a more understanding and easy to interpret way. Like an answer key.arrow_forwardA. Determine whether the curved arrow(s) shown below generate a valid or invalid resonance structure. Draw the resonance structure that would result from each properly drawn arrow and identify the arrow pushing pattern (i.e. allylic positive charge, allylic lone pair, pi bond between atoms of a different electronegativity, lone pair adjacent to a positive charge, alternating pi bonds in a ring. (a). (b).arrow_forwardDraw the curved arrows to show the resonance structure for the following molecules. ( there are 3 molecules )arrow_forward
- 4)On the following molecules, draw the curved arrows to convert the left-hand resonance structure form to the right-hand resonance structure formarrow_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_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_forward
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