Draw the Lewis structure (including resonance structures) for nitromethane (CH3NO2). For each resonance structure, assign formal charges to all atoms that have formal charge.

Question

Draw the Lewis structure (including resonance structures) for nitromethane ([latex]CH_{3}NO_{2}[/latex]). For each resonance structure, assign formal charges to all atoms that have formal charge.

Accepted Answer

Begin by writing the skeletal structure. For organic compounds, the condensed structural formula (in this case [latex]CH_{3}NO_{2}[/latex]) indicates how the atoms are connected.
Calculate the total number of electrons for the Lewis structure by summing the number of valence electrons for each atom.	Total number of electrons for Lewis structure = # valence e[latex]^{-}[/latex] in C + 3(# valence e[latex]^{-}[/latex] in H) + # valence e[latex]^{-}[/latex] in N +2(# valence e[latex]^{-}[/latex] in O) = 4 + 3(1) + 5 + 2(6) = 24
Place a dash between each pair of atoms to indicate a bond. Each dash counts for two electrons.	(12 of 24 electrons used)
Distribute the remaining electrons, first to terminal atoms, then to interior atoms.	(24 of 24 electrons used)
If there are not enough electrons to complete the octets on the interior atoms, form double bonds by moving lone pair electrons from terminal atoms into the bonding region with interior atoms.
Draw any necessary resonance structures by moving only electron dots. (In this case, you can form a double bond between the nitrogen atom and the other oxygen atom.)
Assign formal charges (FC) to each atom. FC = # valence e[latex]^{-}[/latex] -(# nonbonding e[latex]^{-}[/latex]+[latex]\frac{1}{2}[/latex] # bonding e[latex]^{-}[/latex])	Carbon, hydrogen, and the doubly bonded oxygen atoms have no formal charge. Nitrogen has a +1 formal charge [5 - [latex]\frac{1}{2}[/latex] (8)], and the singly bonded oxygen atom in each resonance structure has a -1 formal charge [6-(6 +[latex]\frac{1}{2}[/latex] (2)].

Question 9.9: Draw the Lewis structure (including resonance structures) fo...

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