Which of the two, \(O+2NCH_2CH_2O^- \,or \,CH_3CH_2O^–\)is expected to be more stable and why?
Solution and Explanation
NO2 group is an electron-withdrawing group. Hence, it shows -I effect. By withdrawing the electrons toward it, the NO2 group decreases the negative charge on the compound, thereby stabilizing it. On the other hand, the ethyl group is electron-releasing. Hence, the ethyl group shows the +I effect. This increases the negative charge on the compound, thereby destabilizing it. Hence, O2NCH2CH2O- is expected to be more stable than CH3CH2O-.
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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:
- 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