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Give explanation for each of the follow...

Give explanation for each of the following :
(i) Why are amines less acidic than alcohols of comparable molecular masses ?
(ii). Why do primary amines have higher boiling points han tertiary amines ?
iii. Why are aliphatic amines stroner bases than aromatic amines ?

Text Solution

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(i) Loss of a proton from an amine gives an amide ion while loss of a proton from alcohol gives an alkoxide ion as shown below:
`underset("Amide")(R-NH_(2))tounderset("Amide ion")(R-NH^(-))+H^(+)`
`R-O-H to R-O^(-)+H^(+)`
Since O is more electronegative than N, therefore, `RO^(-)` can accommodate the -ve charge more easily than the `RNH^(-)` can accommodate the negative charge. In other words, `RO^(-)` is more stable than `RNH^(-)`. thus, alcohols are more acidic than amines. conversely, amines are less acidic than alchols.
(ii). Due to the presence of two H-atoms on N-atom of primary amines, they undergo extensive intermolecular H-bonding while tertiary amines due to the absence of a H-atom on the N-atom on the N-atom, do not undergo H-bonding. as a result, primary amines have higher boiling points than tertiary amines of comparable molecular masses. for example, boiling points of n-butylamine (b.p. 351 K) is much higher than that of tert-butylamine (b.p. 319K)
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