Concept explainers
Interpretation:
The structure that is not a permissible contributing one amongst the given structures is to be determined; the remaining three structures are to be ranked in the order of their contribution to the resonance hybrid; and the electron movement that connects these three resonance contributors is to be shown using curved arrows.
Concept introduction:
According to the resonance concept, Lewis formulas that have different distribution of electrons in their structure can be written for a single molecule. Lewis formulas that confer to a resonance hybrid can be made easier to understand by using curved arrows to represent the delocalized electrons.
Each structure contributing to resonance must have an equal total number of valence electrons and the same value of net charge. Among the various Lewis formulas written for a molecule, the formal charges on individual atoms may vary. Each structure contributing to resonance must have the same number of unshared electrons.
When two or more structures satisfy the octet rule, the major contributor structure is the one with the smallest separation of oppositely charged atoms. The contributor structure with the least number of formal charges is more stable.
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Chapter 1 Solutions
Organic Chemistry - Standalone book
- Consider Lewis formulas A, B, and C:(a) Are A, B, and C constitutional isomers, or are they resonance contributors? (b) Which have a negatively charged carbon? (c) Which have a positively charged carbon? (d) Which have a positively charged nitrogen? (e) Which have a negatively charged nitrogen? (f) What is the net charge on each? (g) Which is a more stable structure, A or B? Why? (h) Which is a more stable structure, B or C? Why? (i) What is the CNN geometry in each according to VSEPR?arrow_forward(a) Draw all resonance contributors of the following ion. In drawing each additional resonance structure, use curved arrows to indicate which pairs of electrons are being shifted. (b) Draw the resonance hybrid. (c) Which c–C bond is the longest?arrow_forwardThe 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_forward
- The 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_forwardidentify which is the most and least basic among the given. refer to the number and stability of their resonance structure.arrow_forwardDraw 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)arrow_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_forward(a) In one of the two boxes below, draw a wedge and dashed wedge structure (picture) of CH3Cl that best illustrates the geometry about the central atom. In the other box, draw another picture of the model from a different angle (viewpoint). (b) In CH3Cl, are the three hydrogen atoms equivalent (i.e., do they have identical environments with respect to the other atoms adjacent to themselves)? Briefly explain the evidence for your answerarrow_forwardTrue or False: In resonance energy transfer, the excited electron decays down to an orbital in the same molecule. (a). True (b).Falsearrow_forward
- (a) Draw all valid resonance contributors for this iIon. Show how the electrons can be moved using curved arrOWs. (b) Draw the resonance hybrid.arrow_forwardAnother reagent that can be used to convert carboxylic acids into acid chlorides is phosphorus trichloride (PCI3), as shown in the scheme below. :0: :0: :ö: PCI2 + -PCI2 H. H :O: + НОРCI2 The mechanism, for the reaction, is shown above but the curved arrows and the formal charges, on the respective atoms, have been omitted. (a) Draw the missing curved arrows for each step (b) Supply any missing formal chargesarrow_forwardExplain with the help of resonance structures which of the two nitrogen atoms is more basic in the following molecule.arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning