# Why do alcohols not undergo resonance?

Take for example $\ce{CH3OH}$. The lone pair on the oxygen atom may be donated to form a double bond and giving $\ce{CH3-}$ and $\ce{O+}$ ? Is it because we cant have + charge on $\ce{O}$ atom?

• Octet rule is broken on the carbon. – orthocresol Dec 16 '15 at 3:13
• Please tell me do you the conditions for resonance to take place!! – shaistha Dec 16 '15 at 9:52
• To see a similar substance that can undergo resonance, look at phenol. (Alcohols like vinyl alcohol really overdo it, they isomerize to aldehydes). – AlaskaRon Dec 17 '15 at 4:18

## 1 Answer

It looks like I misread the question which meant the structure $\ce{H_3C- =O^+-H}$ rather than $\ce{H_3C^- O^+}$ which I assumed previously. This structure is not possible because the carbon atom's octet is violated, as it has 10 electrons around itself. Carbon should always have an octet structure (if possible) or lesser number of electrons (like in carbocations) in the resonance contributor structures.

• O would still have 8 el. but C gets 10 and that's the problem – Mithoron Dec 16 '15 at 11:36
• oh sorry I shall edit.I got confused by the CH3- O+ part in the question – Aditya Anand Dec 16 '15 at 11:48
• @Mithoron I have edited my answer. – Aditya Anand Dec 16 '15 at 11:58
• You'd better integrate those parts, You don;t have to use this EDIT convention. – Mithoron Dec 16 '15 at 12:04