Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Which of the following is an acceptable resonance structure for the species shown below?
Options
- ACH ₂ CH ₂ O
- BCH ₃ C H - OH
- CCH ₃ CH = O H
- DCH ₂= O - CH ₃
Correct answer
D. CH ₂= O - CH ₃
Step-by-step solution
The given species is a carbocation with the structure H₂C^ - O - CH₃ . In this structure, the positively charged carbon atom has an incomplete octet (6 valence electrons). The adjacent oxygen atom has two lone pairs of electrons. One of these lone pairs can be delocalized to form a bond between the carbon and oxygen atoms, thereby completing the octet of the carbon atom. The movement of electrons can be shown as: H₂C^ - O - CH₃ H₂C = O^ - CH₃ In the resulting resonance structure, CH₂= O -CH₃ , all atoms (except hyd