CHEM1101 Worksheet 6: Lewis Structures
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1 CHEM1101 Worksheet 6: Lewis Structures Model 1: Simple Compounds of C, N, O and F The octet rule tells us that C, N, O and F will form covalent bonds so that they are surrounded by eight electrons. For C, N, and O, this can give rise to compounds with single or multiple bonds. 1. The following table shows some common simple molecules containing C, N, O or F. For the atom in bold, fill in the number of single, double and triple bonds surrounding it, and the number of lone electron pairs. Compound Number of single bonds Number of double bonds Number of triple bonds Number of lone electron pairs 2. Based on your answers in the table above, fill in the following table to show how many lone electron pairs and how many bonds C, N, O and F need to have to satisfy the octet rule. For total number of bonds, count a triple bond as 3 and a double bond as 2 (e.g. 1 triple bond + 1 single bond = 4). Atom Number of lone electron pairs Total number of bonds C N O F
2 Model 2: Formal Charge For some molecules, not every atom can have its preferred number of bonds and lone electron pairs. Formal charge can be a useful concept in determining the most likely Lewis structure for a compound. In general, preferred structures will have minimised formal charges on each atom. In order to calculate the formal charge of an atom in a molecule, three things must be determined: the number of valence electrons of the element the number of electrons that the atom has in lone pairs the number of electrons that the atom shares in bonds Formal charge can be calculated by the following formula: Formal charge = (valence electrons) (lone pair electrons) ½ (shared electrons) A negative formal charge means that an atom has more electrons than it does in atomic form, while a positive formal charge means that it has fewer electrons. 1. For the following Lewis structures, determine the formal charge of each atom. 2. For the species in question 1, determine the sum of the formal charges. How does this relate to the overall charge of the compound? Model 3: Lewis Structures Lewis structures can give us information about the connectivity between atoms in molecules. The steps for drawing Lewis structures are: Step 1. Count the total number of valence electrons on the molecule Step 2. Draw single bonds between the atoms Step 3. Count how many electrons are left and assign them as lone pairs to fill the valence shells Step 4: If there are unfilled valence orbitals, share the lone pairs to fill the valence orbitals Step 5: If there is more than one possible plausible structure, then we consider both (all) to be resonance structures Step 6: Minimise the formal charges on all atoms
3 1. Formic acid has a formula of CH 2 O 2. Two possible Lewis structures are shown below. Calculate the formal charges on all atoms in the two structures, and predict which Lewis structure better reflects the structure of formic acid. 2. Formic acid can lose the H + bound to the oxygen atom to give the conjugate base, formate (CHO 2 - ). Draw the resulting ion, and calculate the formal charges of each atom. 3. There is a second resonance form of formate, in which the other oxygen atom has the negative charge. Draw the other resonance form, based on your answer to question One resonance structure of nitric acid is shown below. Draw the other resonance structure. 5. What are the bond orders of the three N-O bonds in nitric acid, taking into account the resonance forms? 6. The proton of nitric acid can be removed to give the nitrate anion, NO 3 -. Draw the Lewis structures of all the resonance forms of nitrate.
4 Model 4: Lewis Structures for Organic Molecules Organic molecules contain carbon and hydrogen and may also contain other atoms such as O and N. The ability of C, N and O to make single and multiple bonds means that there is a huge number of possible organic molecules. 1. Draw the Lewis structures of the molecules below. Make sure that you use all of the electrons that are available. Lewis Structure (a) C 3 H 8 (b) H 2 CO (c) CH 3 OCH 3
5 2. Complete the Lewis structures of the molecules below by filling in multiple bonds and lone electron pairs. Molecules are not charged, unless otherwise specified. glycine (an amino acid) guanine (nitrogen base in DNA) aspirin acetate phenoxide (hint: for the second resonance form, use a C=O double bond.) 3. Assign the formal charges on the Lewis structure of trinitrotoluene (TNT) below.
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