Question:

Identify the reagents shown in bold in the following equations as nucleophiles or electrophiles. 
(a) \(CH_3COOH+HO^{–6} \rightarrow CH_3COO^–+H_2O\) 
(b) \(CH_3COCH^{3+} C^–N\rightarrow (CH_3)_2C(CN)(OH)\)
(c) \(C_6H_6 + CH_3C+O^+ \rightarrow C_6H_5COCH_3\)

Updated On: Nov 16, 2023
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Solution and Explanation

Electrophiles are electron-deficient species and can receive an electron pair. On the other hand, nucleophiles are electron-rich species and can donate their electrons.


\((a) \,\,CH_3COOH+HO^-→CH_3COO^-+H_2O\)
Here, HO- acts as a nucleophile as it is an electron-rich species, i.e., it is a nucleus-seeking species.


\((b) \,\,CH_3COCH+CN^-→(CH_3)C(CN)+(OH)\)
Here, -CN acts as a nucleophile as it is an electron-rich species, i.e., it is a nucleus-seeking species.


\((b) \,\,CH_6+CH_3CO→C_6H_3COCH_3\)
Here, \(CH_3C^+O\) acts as an electrophile as it is an electron-deficient species.

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Top Questions on Organic Chemistry- Some Basic Principles and Techniques

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Concepts Used:

Organic Chemistry – Some Basic Principles and Techniques - Reaction Mechanism

SN1 Reaction Mechanism:

SN1 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:

  1. A new sigma bond from C=C is formed during the reaction in the arene nucleophile.
  2. Due to the breaking of the C-H sigma bond, a proton is removed.
  3. 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