Question:

In HS^-,I^-,R–NH₂, NH₃ order of proton excepting tendency will be :-

Updated On: Apr 21, 2025

I^- > NH₃ > R–NH₂ > HS^-
NH₃ > R-NH₂ > HS_- > I^-
RNH₂ > NH₃ > HS^-> I^-
HS^-> RNH₂ > NH₃ > I^-

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The Correct Option is C

Solution and Explanation

The correct option is (C): RNH₂ > NH₃ > HS^-> I^-
The order of proton-accepting tendencies is as follows: R−NH₂ > NH₃ > HS^- > I^-.
The reduced proton-accepting ability of the iodide ion is attributed to its larger size, which leads to a lower charge density due to the negative charge being distributed over a larger area. Conversely, alkylamines exhibit a greater propensity to accept protons compared to ammonia, owing to the +I (inductive effect) influence of the alkyl group.

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Concepts Used:

Organic Chemistry – Some Basic Principles and Techniques - Reaction Mechanism

SN1 Reaction Mechanism:

S_N¹ reaction mechanism takes place by following three steps –

Formation of carbocation
Attack of nucleophile
Deprotonation

SN2 Reaction Mechanism:

The SN2 reaction mechanism involves the nucleophilic substitution reaction of the leaving group (which generally consists of halide groups or other electron-withdrawing groups) with a nucleophile in a given organic compound.

Electrophilic Aromatic Substitution Reaction Mechanism:

The mechanism of an electrophilic aromatic substitution reaction contains three main components which are:

A new sigma bond from C=C is formed during the reaction in the arene nucleophile.
Due to the breaking of the C-H sigma bond, a proton is removed.
The C=C bond is reformed and it restores the aromaticity of the compound.

Electrophilic Substitution Reaction Mechanism:

The electrophilic substitution reaction mechanism is composed of three steps, which will be discussed more below.

Electrophile Generation
Carbocation Formation
Proton Removal

In HS-,I-,R–NH2, NH3 order of proton excepting tendency will be :-