Draw the resonance structures for the following compounds. Show the electron shift using curved-arrow notation.
(a) \(C_6H_5OH \)
(b) \(C_6H_5NO_2\)
(c) \( CH_3CH=CHCHO\)
(d) \(C_6H_5–CHO \)
(e) \(C_6H_5–C+H_2\)
(f) \(CH_3CH=CH C+H_2\)
(a) \(C_6H_5OH \)
(b) \(C_6H_5NO_2\)
(c) \( CH_3CH=CHCHO\)
(d) \(C_6H_5–CHO \)
(e) \(C_6H_5–C+H_2\)
(f) \(CH_3CH=CH C+H_2\)
Solution and Explanation
(a) The structure of C6H5OH is:
The resonating structures of phenol are represented as:
(b) The structure of C6H5NO2 is:
The resonating structures of nitrobenzene are represented as:
(c) CH3CH = CH - CHO
The resonating structures of the given compound are represented as:
(d) The structure of C6H5CHO is:
The resonating structures of benzaldehyde are represented as:
(e) C6H5-C+H2
The resonating structures of the given compound are:
(f) CH3CH = CHC+H2
The resonating structures of the given compound are:
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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