Concept explainers
Interpretation:
For each of the given compounds, the contributing resonance structures and resonance hybrid are to be written by adding missing unshared electron pairs and curved arrows.
Concept introduction:
Resonating structures are structures that have more than one equivalent Lewis structure for the same molecule or ion.
According to the convention, these structures are connected by double-headed arrows (
Movement of electrons (whether bonding or lone pair) is indicated by curved arrows.
The rules for writing the resonance structures are:
Resonance structures have existence in paper only, they are not real structures.
While writing the resonance structures, movement of either double bonded electrons or lone pair of electrons are shown.
All structures should be correct Lewis structures.
The energy of any contributing structure is higher than the energy of the resonance hybrid.
For equivalent resonating structures, the resonance stabilization is large.
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ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
- Problem 1.41 Write the condensed structure of a compound that contains only carbon and hydrogen atoms and that has Part A two sp³ hybridized carbons. Express your answer as a condensed structural formula. α Submit ΑΣΦ В Part B Y V CH₂CH₂ H A chemical reaction does not occur for this question. X Previous Answers Request Answer X Incorrect; Try Again; 4 attempts remaining ΑΣΦ ? one sp³ hybridized carbon and two sp² hybridized carbons. Express your answer as a condensed structural formula. Submit Request Answer ? A chemical reaction does not occur for this question.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_forwardProblem Draw Lewis structures for the following:(a) Ethylene (C2H4), the most important reactant in the manufacture of polymers(b) Nitrogen (N2), the most abundant atmospheric gasPlan We show the structure resulting from steps 1 to 4: placing the atoms, counting the total valence electrons, making single bonds, and distributing the remaining valence electrons in pairs to attain octets. Then we continue with step 5, if needed.arrow_forward
- Practice problem 1: Show a full octet resonance contributor for thymine, using curved arrows to show its contributor. Add all formal charges, if necessary.arrow_forwardFor the following structure a) draw curved arrows and generate two (2) more valid resonance structures in addition to the initial structure given Be sure to include to show lone pairs and formal charges on your resonance structures. b) Rank the resonance structures in order of decreasing importance: 1 is most important, 2 is second most important, 3 is the least important :0arrow_forward*2.16 For each of the species below, circle the most reactive lone pair or bond and indicate the type of frontier orbital that it represents (n, π, or σ). A B с H₂C CH₂ D NEC +OEN H NH2arrow_forward
- Compute the formal charge (FC) on each atom in the following structures.(a) Methane (CH4)arrow_forwardIdentify all functional groups that are present in strychnine, a highly toxic alkaloid used as a pesticide to kill rodents, whose line structure is shown here. What compound class is characteristic of each of those functional groups? Strychninearrow_forwardConvert the skeletal structure to a complete Lewis structure with all carbon and hydrogen atoms drawn in. Include lone pairs where applicable. 4arrow_forward
- A 1.88/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 HCI. H [1] + H-i: + :ÖH HO [2] + H-i: [3] phenolarrow_forwardT 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 HOarrow_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_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning