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Amines Reason Out

The document discusses various properties and reactions of amines, highlighting differences in boiling points, basicity, and reactivity in electrophilic substitution. It explains why certain amines, like aniline, do not undergo specific reactions and the effects of substituents on their basicity and reactivity. Additionally, it covers the solubility of amines in water and the stability of diazonium salts.

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5 views

Amines Reason Out

The document discusses various properties and reactions of amines, highlighting differences in boiling points, basicity, and reactivity in electrophilic substitution. It explains why certain amines, like aniline, do not undergo specific reactions and the effects of substituents on their basicity and reactivity. Additionally, it covers the solubility of amines in water and the stability of diazonium salts.

Uploaded by

rojabiggboss
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as DOCX, PDF, TXT or read online on Scribd
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Amines:

I.Reason out:

1.Primary amines have higher boiling points than the tertiary amines.

Tertiary amines have no hydrogen atoms bonded to the nitrogen


atom.Thus, tertiary amines cannot form intermolecular hydrogen bonds. As a
result, they have lower boiling points than primary and secondary amines.

2. Aniline does not undergo Friedel-Crafts reaction.


Aniline does not undergo Friedel craft's reactions because the reagent AlCl3
being electron deficient acts as a Lewis acid and attacks on the lone pair of
nitrogen present in aniline to form an insoluble complex which precipitates out
and the reaction does not proceed.

3. (CH3)2NH is more basic than (CH3)3N in an aqueous solution.

(CH3)2NH is more basic than (CH3)3N in an aqueous solution.


(Pg399 refer pic 2) is hydrated to a greater extent than (Refer pic 3 on pg
399). As the number of methyl groups increases, the extent of hydration
decreases due to steric hindrance. Greater is the extent of hydration,
greater is the stability of ion and greater is the basic strength of amine.

4. Acetylation of aniline reduces its activation effect. Why?

Due to resonance the lone pair of electrons on nitrogen of acetanilide gets


delocalised towards carbonyl group.
Hence the electrons are less available for donation to benzene ring by resonance.
Therefore, activation effect of aniline gets reduced after acetylation.

5. CH3NH2 is more basic than C6H5NH2.

In CH3−NH2, +I effect of −CH3 group increases the electron density on


the −N atom making the lone pair more available for donation. On the other
hand, in aniline lone pair of electron on the nitrogen atom is delocalised over the
benzene ring due to resonance and thus making it less available for donation.
That is why CH3−NH2 is more basic than C6H5−NH2

6. Although −NH2 is o/p directing group, yet aniline on nitration gives a significant
amount of m-nitroaniline.

Nitration is carried out in an acidic medium. In an acidic medium, aniline is


protonated to give anilinium ion (which is meta-directing).
7. Aromatic diazonium salts are more stable than aliphatic diazonium salts.
Resonance is observed in aromatic diazonium salts which leads to the
delocalisation of positive charge. No such resonance is observed in aliphatic
diazonium salts. Hence, aromatic diazonium salts are more stable than aliphatic
diazonium salts.

8. Aromatic primary amines cannot be prepared by Gabriel phthalimide synthesis.


(Or ) Gabriel phthalimide synthesis is preferred for synthesizing primary
amines.
Because C-X bond in haloarene (aryl halide) is difficult to be cleaved due to
partial double bond character.So, aromatic primary amines cannot be
prepared by Gabriel phthalimide synthesis

9. Aliphatic amines are stronger bases than ammonia.(or)Aromatic amines are less
basic than aliphatic amines.

In aliphatic amines, the −NH2 group is attached to an alkyl group which is an


electron donating group i.e, they have +I effect. So, the lone pair of electrons on
nitrogen are readily available.
In aromatic amines, the −NH2 group is attached to a −C6H5 group, which is an
electron withdrawing group. So, the availability of a lone pair of electrons on N is
decreased. Therefore aliphatic amines are more basic than aromatic amines.

10. pKb of aniline is more than that of methylamine.

Higher the value of pKb lesser is the basic character .


Aniline has higher pKb than methylamine because methylamine is more basic
than aniline as in methylamine delocalisation of lone pair of electrons belonging
to nitrogen occurs as a result resonance structures are formed which increase the
basic character of methylamine as a result it has lesser pKb value.

11. Ethylamine is soluble in water whereas aniline is not.

1. Ethylamine is soluble in water owing to its potential to form


intermolecular Hydrogen bonds with water. On the other hand, aniline
does not undergo hydrogen bonding because of the presence of the
benzene which is highly hydrophobic. Therefore aniline is insoluble in
water.

12. p-methylaniline is more basic than p-nitroaniline.


(EWG- Decreases the electron density- less basic)-NO2
In the case of p-Nitroaniline, Aniline is substituted with an electron
withdrawing nitro group which decreases the electron density on the
nitrogen atom. This makes the lone pair of electrons on nitrogen less
available for donation, making it less basic. Thus, p-Methylaniline is
more basic than p-Nitroaniline.

13.Before nitration aniline is converted into acetanilide

During direct nitration aniline is converted to anilinium ion which is ring


deactivating and meta directing group. Hence, in order to retain it,ortho/para
directing group is converted into acetanilide.

14.Methylamine in water reacts with ferric chloride to precipitate hydrated


ferric oxide.

Methylamine in water reacts with ferric chloride to precipitate hydrated ferric


oxide.
The +I effect of methyl group makes methyl amine more basic than water.
Methyl amine reacts with water to produce hydroxide ions.
CH3−NH2+H2O→CH3−NH3+ + OH−
Hydroxide ions react with ferric chloride to precipitate hydrated ferric oxide ( Fe2
O3⋅3H2O).
2FeCl3+6OH−→Fe2O3⋅3H2O+6Cl−

15.Amines are les acidic than alcohols of comparable molecular masses.

Amines lose a proton to form amide ion. Alcohols lose a proton to form alkoxide
ion.

O is more electronegative than N, the negative charge is more easily


accomodated in RO− than in R−NH−. Hence, amines are less acidic than
alcohols of comparable molecular masses.
16.Ammonolysis of alkyl halide does not give corresponding amines in pure
state.

This is because the amine formed reacts further with more of alkyl halide to
give 2∘ and 3∘ amines and finally quaternary salt. Thus a mixture of amines
is obtained.
17.If NO2 or COOH groups are attached to a carbon of benzene ring electrophilic
substitution becomes difficult.

Because they are electron withdrawing group,So they decrease the electron density on
the benzene ring.

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