Chapter 1, Problem 26EQ

The skeleton is benzaldoxime is

The number of valence electrons is as follows: from the phenyl group. ___; from each of two hydrogens, ___; from the carbon atom, ___; from the nitrogen atom, ___; and from the oxygen atom, ___, for a total of ___. Filling in the skeleton with single bonds and adding the appropriate unshared pairs gives

_____________________

The number of electrons in the functional group of this trial structure is ___, which is ___ too many. Removing an unshared pair from carbon and nitrogen and adding a second bond between them gives

_____________________

in which carbon, nitrogen, and oxygen have their customary valences of ___, ___, and respectively. The alternative structure with a double bond between nitrogen and oxygen is

_____________________

This structure is not acceptable because it requires carbon and oxygen to exhibit the unfamiliar valences of ___ and ___.

Derive Lewis structures for the compounds below.