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Answer and Explanation
The basicity of these compounds depend on the attached group to the Nucleophilic Nitrogen centre. The more any of the attached groups, pulls the electrons towards itself, the less basic the compound is.
a) a) Methylamine (CH3NH2) > Ammonia (NH3) > aniline (C6H5NH2)
An alkyl group is electron releasing and base strenghtening, while an aryl (C6H5) group is electron withdrawing and base weakening.
b) N-methylaniline (C6H5NHCH3) > aniline (C6H5NH2) > Acetanilide (C6H5NH(C=O)CH2)
An acetyl group is an electron-withdrawing and base-weakening substituent, especially when bonded directly to nitrogen. Amides are weaker bases than amines, and thus acetanilide is a weaker base than aniline. Alkyl groups are electron-releasing; N-methyl aniline is a slighly stronger base than aniline.
c) 2,4-dimethylaniline > 2,4-Dichloroaniline > 2,4-dinitroaniline
The chemical structure for (c) and (d) is drawn in the attachment to this question.
Chlorine substituents are slightly electron-withdrawing, and methyl groups are slightly
electron-releasing. 2,4-Dimethylaniline is therefore a stronger base than 2,4-dichloroaniline. Nitro groups are strongly electron-withdrawing. Their base-weakening effect being especially
pronounced when a nitro group is ortho or para to an amino group because the two groups are then directly conjugated.
d) 3,4-Dichloroaniline > 4-chloro-3-nitroaniline > 4-chloro-2-nitroaniline,
Nitro groups are more electron-withdrawing than chlorine, and the base-weakening effect of a nitro substituent is greater when it is ortho or para to an amino group than when it is meta to it.
e) Dimethylamine (CH3(NH)CH3) > N-methylaniline (C6H5(NH)CH3) > diphenylamine (C6H5(NH)C6H5)
According to the principle applied in part (a) (alkyl groups increase basicity, aryl groups decrease it).
QED!
The study of chemicals is called chemistry.
The correct answer is as follows:-
The basicity of these compounds depends on the attached group to the Nucleophilic Nitrogen center.
The more any of the attached groups pull the electrons towards themselves, the less basic the compound is.
The order of the basicity is as follows:-
a) Methylamine [tex](CH_3NH_2)[/tex] > Ammonia [tex](NH_3)[/tex] > aniline [tex](C_6H_5NH_2)[/tex]
An alkyl group is an electron releasing and base strengthening, while an aryl (C6H5) group is electron-withdrawing and base weakening.
The order of the basicity is as follows:-
b) N-methylaniline [tex](C_6H_5NHCH_3)[/tex] > aniline[tex](C_6H_5NH_2)[/tex] > Acetanilide [tex](C_6H_5NH(C=O)CH_2)[/tex]
An acetyl group is an electron-withdrawing and base-weakening substituent, especially when bonded directly to nitrogen.
Amides are weaker bases than amines, and thus acetanilide is a weaker base than aniline. Alkyl groups are electron-releasing; N-methyl aniline is a slightly stronger base than aniline.
The order of the basicity is as follows:-
c) 2,4-dimethylaniline > 2,4-Dichloroaniline > 2,4-dinitroaniline
The order of the basicity is as follows:-
d) 3,4-Dichloroaniline > 4-chloro-3-nitroaniline > 4-chloro-2-nitroaniline,
Nitro groups are more electron-withdrawing than chlorine, and the base-weakening effect of a nitro substituent is greater when it is ortho or para to an amino group than when it is meta to it.
The order of the basicity is as follows:-
e) Dimethylamine [tex](CH_3(NH)CH_3)[/tex] > N-methyl aniline [tex](C_6H_5(NH)CH_3)[/tex] > diphenylamine [tex](C_6H_5(NH)C_6H_5)[/tex]
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