Concept explainers
Interpretation:
The carbon–oxygen bond lengths and the equal negative charge on oxygens of an acetate ion are to be explained by drawing resonance structures.
Concept introduction:
Resonance is the phenomenon of describing delocalized electrons in certain molecular ions through various forms or resonance structures and the forms contributing to the hybrid form.
The positions of electrons are different, without effecting the positions of the nuclei.
The effect of delocalization is caused by resonance, where the negative charge is distributed among the oxygen atoms in a carboxylate ion.
The rules for drawing resonance structures are as follows:
Only nonbonding electron pairs and pi electrons can participate in conjugation in the formation of various resonating structures.
The single bonds present in the molecule do not break or form in the resonance structures.
The placement of atoms present in the molecule remains fixed.
The octet of all atoms is completely filled.
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Organic Chemistry
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- 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_forwardThe 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_forwardFor each pair of compounds, predict which one has the higher molecular dipole moment, and explain your reasoning.(a) ethyl chloride or ethyl iodidearrow_forward
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- For 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_forwardB. Draw all significant resonance structures of each compound below. Include the necessary curved arrows to generate each resonance structure and any formal charges. If no valid resonance structures can be generated, write NONE next to structure. (a). (b).arrow_forwardb) Below draw 2 examples for: (i) Polar protic solvent (ii) Polar aprotic solvent (iii) One example for non-polar solventarrow_forward
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