Advices For Studying Organic Chemistry

3.12 ORGANIC COMPOUNDS AS BASES

3.12A Organic Bases

1. An organic compound contains an atom with an unshared electron pair is a
   potential base.

1. H 3 C O + O+
   H

H Cl H 3 C +

H

H Cl−

Methanol Methyloxonium ion

(a protonated alcohol)

i) The conjugate acid of the alcohol is called a protonated alcohol (more

formally, alkyloxonium ion).

2)

R O + O+

H

H A R +

H

H A−

Alcohol Strong acid Alkyloxonium ion Weak base

3)

R O + O+

R

H A R +

R

H A−

Alcohol Strong acid Dialkyloxonium ion Weak base

4)

C O O+

R

R

+ H A + A−

Ketone Strong acid Protonated ketone Weak base

C

R

R

H

5) Proton transfer reactions are often the first step in many reactions that

alcohols, ethers, aldehydes, ketones, esters, amides, and carboxylic acids

undergo.