Read the passage given below and answer the questions based on it.
Amines constitute an important class of organic compounds derived by replacing one or more hydrogen atoms of ammonia molecule by alkyl/aryl group(s). Like ammonia, nitrogen atom of amines is trivalent and carries an unshared pair of electrons. Nitrogen orbitals in amines are therefore sp3 hybridised and the geometry of amines is pyramidal. Amines are classified as primary (1°), secondary (2°) and tertiary (3°) depending upon the number of hydrogen atoms replaced by alkyl or aryl groups in ammonia molecule. Due to the electron releasing nature of alkyl group, it (R) pushes electrons towards nitrogen and thus makes the unshared electron pair more available for sharing with the proton of the acid. Moreover, the substituted ammonium ion formed from the amine gets stabilised due to dispersal of the positive charge by the +I effect of the alkyl group. Hence, alkyl amines are stronger bases than ammonia. Thus, the basic nature of aliphatic amines should increase with increase in the number of alkyl groups. The order of basicity of amines in the gaseous phase follows the expected order: 3° > 2° > 1° > NH3. Adrenaline and ephedrine, both containing a secondary (2°) amino group, are used to increase blood pressure. The well-known antihistaminic drug Benadryl contains a tertiary (3°) amino group.
Among the following, the weakest base is:
Answer & explanation
Correct answer: option 4
The correct answer is Option (4) → \(NH_3\)
In water, the basic strength of alkyl amines is decided by the +I effect of the alkyl groups (which makes the lone pair more available), by solvation of the protonated amine (better with more N–H hydrogens), and by steric hindrance. For ethyl amines the result is:
\( \ce{(C2H5)2NH} \) > \( \ce{(C2H5)3N} \) > \( \ce{C2H5NH2} \) > \( \ce{NH3} \)
Every alkylamine is a stronger base than ammonia, which has no electron-releasing alkyl group, so NH3 is the weakest base here.
NCERT (2026-27 edition):
Chemical Reactions – “… Thus, there is a subtle interplay of the inductive effect, solvation effect and steric hinderance of the alkyl group which decides the basic strength of alkyl amines in the aqueous state. The order of basic strength in case of methyl substituted amines and ethyl substituted amines in aqueous solution is as follows:
\( \ce{(C2H5)2NH > (C2H5)3N > C2H5NH2 > NH3} \)
\( \ce{(CH3)2NH > CH3NH2 > (CH3)3N > NH3} \)”