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 C-N bond. Draw one or more resonance structures that support this observation.

First, let's determine the total number of valence electrons in the N, N-dimethylformamide molecule by examining each element: - Carbon (C) has 4 valence electrons - Nitrogen (N) has 5 valence electrons - Oxygen (O) has 6 valence electrons - Hydrogen (H) has 1 valence electron Now, let's determine the total number of valence electrons within the N, N-dimethylformamide molecule: 1 Carbon atom = 1 * 4 = 4 1 Oxygen atom = 1 * 6 = 6 2 Nitrogen atoms = 2 * 5 = 10 7 Hydrogen atoms = 7 * 1 = 7 Total number of valence electrons: 4 + 6 + 10 + 7 = 27

First, we will draw the skeletal structure of the N, N-dimethylformamide molecule. The skeletal structure is given as: H N - C - O | C / \ H H Next, arrange the remaining valence electrons to satisfy the octet rule for each atom. Start placing lone pairs on atoms from O and N. The initial Lewis structure of N, N-dimethylformamide with all atoms satisfying octet rule looks like this: H N - C = O | C / \ H H There are no remaining valence electrons. All atoms follow the octet rule except for hydrogens, which follow the duet rule.

To show the double bond character in the C-N bond, we can draw a resonance structure of the N, N-dimethylformamide molecule. We can move a lone pair from N to form a double bond between the C and N. The resonance structure of N, N-dimethylformamide with double bond character in the C-N bond looks like this: H N = C - O | C / \ H H Please note the following resonance contributors for the N, N-dimethylformamide molecule: · H N - C = O with a single C-N bond and a double C=O bond · H N = C - O with a double C=N bond and a single C-O bond The actual structure is a hybrid of these two resonance contributors. This explains the observed double bond character in the C-N bond.