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Chapter 8: Problem 152

Draw a Lewis structure for the \(N, N\) -dimethylformamide molecule. The skeletal structure is Various types of evidence lead to the conclusion that there is some double bond character to the \(\mathrm{C}-\mathrm{N}\) bond. Draw one or more resonance structures that support this observation.

Short Answer

Expert verified
The Lewis structure for the N, N-dimethylformamide molecule is: H | H-C=N-C-H || | O H The resonance structures that support the double bond character of the C-N bond are: H | H-C=N-C-H || | O H H | H-C-N=C-H | \\ | O H These resonance structures indicate the delocalization of electrons in the C-N bond, and the actual structure of the molecule lies in between these two resonance structures.

Step by step solution

01

Determine the total number of valence electrons

First, we need to determine the total number of valence electrons in the molecule. The molecule consists of: - 1 Carbon (C) atom - 4 valence electrons - 1 Nitrogen (N) atom - 5 valence electrons - 3 Oxygen (O) atoms - (3x6) = 18 valence electrons - 6 Hydrogen (H) atoms - (6x1) = 6 valence electrons Total valence electrons = 4 + 5 + 18 + 6 = 33
02

Draw the Lewis structure

Based on the given skeletal structure - H | H-C-N-C-H | | O H Now, we will distribute the valence electrons to create a stable structure. We start by giving each atom an octet (except for hydrogen, which only requires two electrons). H | H-C=N-C-H || | O H We have achieved the stable structure with the correct number of valence electrons (33). The central carbon and nitrogen atoms have an octet, and the two terminal carbons have duets.
03

Draw resonance structures

Resonance structures show the delocalization of electrons in the molecule, which explains the double bond character of the C-N bond. We can show this by drawing a second resonance structure where the electrons are rearranged: H | H-C-N=C-H | \\ | O H These resonance structures represent the delocalization of electrons in the C-N bond. The actual structure of the N, N-dimethylformamide lies in between these two resonance structures, indicating that there is some double bond character to the C-N bond.

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Most popular questions from this chapter

Given the following information: Heat of sublimation of \(\operatorname{Li}(s)=166 \mathrm{~kJ} / \mathrm{mol}\) Bond energy of \(\mathrm{HCl}=427 \mathrm{~kJ} / \mathrm{mol}\) Ionization energy of \(\operatorname{Li}(g)=520 . \mathrm{kJ} / \mathrm{mol}\) Electron affinity of \(\mathrm{Cl}(g)=-349 \mathrm{~kJ} / \mathrm{mol}\) Lattice energy of \(\operatorname{LiCl}(s)=-829 \mathrm{~kJ} / \mathrm{mol}\) Bond energy of \(\mathrm{H}_{2}=432 \mathrm{~kJ} / \mathrm{mol}\) Calculate the net change in energy for the following reaction: $$ 2 \mathrm{Li}(s)+2 \mathrm{HCl}(g) \longrightarrow 2 \mathrm{LiCl}(s)+\mathrm{H}_{2}(g) $$

What do each of the following sets of compounds/ions have in common with each other? See your Lewis structures for Exercises 107 through 110 . a. \(\mathrm{XeCl}_{4}, \mathrm{XeCl}_{2}\) b. \(\mathrm{ICl}_{5}, \mathrm{TeF}_{4}, \mathrm{ICl}_{3}, \mathrm{PCl}_{3}, \mathrm{SCl}_{2}, \mathrm{SeO}_{2}\)

Write Lewis structures that obey the octet rule (duet rule for \(\mathrm{H}\) ) for each of the following molecules. a. \(\mathrm{H}_{2} \mathrm{CO}\) b. \(\mathrm{CO}_{2}\) c. HCN Except for \(\mathrm{HCN}\) and \(\mathrm{H}_{2} \mathrm{CO}\), the first atom listed is the central atom. For \(\mathrm{HCN}\) and \(\mathrm{H}_{2} \mathrm{CO}\), carbon is the central atom. Carbon is the central atom in all of these molecules.

Compare and contrast the bonding found in the \(\mathrm{H}_{2}(\mathrm{~g})\) and \(\mathrm{HF}(\mathrm{g})\) molecules with that found in \(\operatorname{NaF}(s)\).

Use the following standard enthalpies of formation to estimate the \(\mathrm{N}-\mathrm{H}\) bond energy in ammonia: \(\mathrm{N}(\mathrm{g}), 472.7 \mathrm{~kJ} / \mathrm{mol} ; \mathrm{H}(\mathrm{g})\), \(216.0 \mathrm{~kJ} / \mathrm{mol} ; \mathrm{NH}_{3}(g),-46.1 \mathrm{~kJ} / \mathrm{mol}\). Compare your value to the one in Table \(8.4\).
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