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Chapter 9: Problem 102

Methyl isocyanate \(\left(\mathrm{CH}_{3} \mathrm{NCO}\right)\) is used to make certain pesticides. In December \(1984,\) water leaked into a tank containing this substance at a chemical plant, producing a toxic cloud that killed thousands of people in Bhopal, India. Draw Lewis structures for \(\mathrm{CH}_{3} \mathrm{NCO},\) showing formal charges.

Short Answer

Expert verified
The Lewis structures for CH3NCO shows three single bond between N-C, N-C and H-C. There is a double bond between N-O. The oxygen atom has a lone pair of electrons and formal charges on all atoms are zero.

Step by step solution

01

Count Total Electrons

The total number of valence electrons in the molecule can be calculated by adding the number of valence electrons each individual atom contributes. Carbon (C) has 4 valence electrons, Nitrogen (N) has 5, Oxygen (O) has 6 and Hydrogen has 1 valence electron each, summing up to a total of 14 valence electrons.
02

Draw the Skeletal Structure

The atom that has the highest bond making capacity is placed at the center, hence nitrogen will be at the center. Place the remaining atoms around it, and draw single bond between the center atom and the peripheral atoms. The bonds between NC, CO, and CH will consume 8 electrons. Draw 3 C-H bonds, consuming 3 more electrons, totaling 11 used electrons.
03

Distribute the Remaining Electrons

There will be 3 remaining electrons (out of 14) after forming the bonds. These surplus electrons will be placed on the most electronegative atom, in this case, oxygen. Assign these remaining 3 electrons to the oxygen atom as lone pairs
04

Check the Octet Rule

Each atom in the molecule needs to fulfill the octet rule, except Hydrogen which follows the duet rule. We have a violation at Nitrogen, as it only has 6 electrons, it can form an additional bond using the lone pair of oxygen thereby obeying octet rule and forming a double bond between nitrogen and oxygen.
05

Calculate Formal Charge

Calculate the formal charge of each atom. Formal charge = (Valence electrons on atom) - (Non-bonding electrons + 1/2(bonding electrons)). All atoms (C, N, O, 3 H's) have a formal charge of 0, indicating that we have indeed found the correct Lewis structure.

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Most popular questions from this chapter

A student in your class claims that magnesium oxide actually consists of \(\mathrm{Mg}^{+}\) and \(\mathrm{O}^{-}\) ions, not \(\mathrm{Mg}^{2+}\) and \(\mathrm{O}^{2-}\) ions. Suggest some experiments one could do to show that your classmate is wrong.

List the following bonds in order of increasing ionic character: cesium to fluorine, chlorine to chlorine, bromine to chlorine, silicon to carbon.

Draw Lewis structures for the following organic molecules: (a) methanol \(\left(\mathrm{CH}_{3} \mathrm{OH}\right) ;\) (b) ethanol \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\right) ;\) (c) tetraethyllead \(\left[\mathrm{Pb}\left(\mathrm{CH}_{2} \mathrm{CH}_{3}\right)_{4}\right]\) which was used in "leaded gasoline"; (d) methylamine \(\left(\mathrm{CH}_{3} \mathrm{NH}_{2}\right),\) which is used in tanning; (e) mustard gas \(\left(\mathrm{ClCH}_{2} \mathrm{CH}_{2} \mathrm{SCH}_{2} \mathrm{CH}_{2} \mathrm{Cl}\right),\) a poisonous gas used in World War I; (f) urea [(NH \(_{2}\) ) \(_{2}\) CO], a fertilizer; and (g) glycine \(\left(\mathrm{NH}_{2} \mathrm{CH}_{2} \mathrm{COOH}\right)\), an amino acid.

Are the following statements true or false? (a) Formal charges represent actual separation of charges. (b) \(\Delta H_{\mathrm{rxn}}^{\circ}\) can be estimated from the bond enthalpies of reactants and products. (c) All secondperiod elements obey the octet rule in their compounds. (d) The resonance structures of a molecule can be separated from one another.

Use an example to illustrate each of the following terms: lone pairs, Lewis structure, the octet rule, bond length.
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