ORGANIC COMPOUND CONTAINING NITROGEN - …einsteinclasses.com/JEE Main Website/Chemistry/Or_Co_C_Nit.pdf · ORGANIC COMPOUND CONTAINING NITROGEN ... Aliphatic amines are named by

Einstein Classes, Unit No. 102, 103, Vardhman Ring Road Plaza, Vikas Puri Extn., Outer Ring Road

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ORGANIC COMPOUNDCONTAINING NITROGEN

Sy l labus :

General methods of preparation, properties,reaction and uses.

Amines : Nomenclature, classification, structure,basic character and identification of primary,secondary and tertiary amines and their basiccharacter.

Diazonium Salts : Importance in synthetic organicchemistry.


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CONCEPTS

C1A Structure : of the organic compounds that show appreciable basicity (e.g. those strong enough to

turn litmus blue), by for the most important are the amines. An amine has the general formulaeRNH

2, R

2NH or R

3N where R is an alkyl or aryl group. For e.g.

Nomenclature : Aliphatic amines are named by naming the alkyl group or groups attached tonitrogen and following these by the word-amine e.g.

Salts of amine are generally named by replacing amine by ammonium (or aniline by anilinium), andadding the name of the anion (chloride, nitrate, sulfate etc.) e.g.

C6H

5NH

3+Cl– (C

2H

5NH

3+)

2SO

42–

Anilininum EthylammoniumChloride Sulfate

C1B Physical Properties of amines : Like ammonia, amines are polar compounds and except for tertiaryamines, can form intermolecular hydrogen bonds. Amines have higher boiling points thannon-polar compounds of same molecular weight, but lower boiling points that alcohols or carboxylicacids.


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Amines of all three classes are capable of forming hydrogen bonds with water. As a result smalleramines are quite soluble in water, with borderline solubility is reached with six carbon atoms.

Amines are soluble in less polar solvents like ether, alcohol, benzene etc.

C1C Stereochemistry of Nitrogen : Consider quaternary ammonium salts, compounds in which fouralkyl groups are attached to nitrogen. Here all four sp3 orbitals are used to form bonds and quatenarynitrogen is tetrahedral. Thus quaternary ammonium salts in which nitrogen holds four differentgroups have been found to exist as configurational enantiomers, capable of showing optical activity.

C2 Methods of Preparation :

1. Reduction of Nitro Compounds :

2. Reaction of halides with ammonia or amines :

XRNRNRHNRNHRNH

)4(salts

ammoniumQuaternary

|R

|

RX

Amine3

|R

R|

RX

Amine2

|R

XR

Amine12

RX3

0

R

0

00

RX must be alkyl or aryl with electron withdrawing substituents.

The presence of large excess of ammonia lessens the importance of these last reactions and increasesthe yield of primary amine.

3. Reductive Amination :

C = O + NH3

CNNaBHor

Ni,H

3

2 CH – NH2

10 Amine

C = O + RNH2

CNNaBH

Ni,H

3

2 CH – NHR 20 Amine

C = O + R2NH

CNNaBH

Ni,H

3

2 CH – NR2

30 Amine

4. Reduction of nitriles (Higher carbon number is obtained)

22Catalyst,H2

NHCHRNCR 2


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)(1diamineeneHexamethyl

224222Ni,H

leAdiponitri42

NaCN2222

0

2 NHCH)(CHNCHHCN)CH(NCClCHCHCHClCH

5. Hoffman degradation of amides :

ePentylaminn2423

KOBr

e)(HexanamidCapromide

2423

2322

OBr22

NH)(CHCHCONH)(CHCH

COArNHorNHRArCONHorRCONH

Discussion : From the above reaction it is clear that in this reaction, the rearrangement occurs, sincethe group joined to carbonyl carbon in the amide is found joined to nitrogen in the product.

The reaction is believed to proceed by the following steps :

1.

2.

5. 232

OHCORNHOH2OCNR 2

Steps (3) and (4) are generally takes place simultaneously. The attachment of R to nitrogen helps topushout halide ion.

(3,4)

Step (5) is the hydrolysis of an isocyanate (R – N = C = O) to form amine and carbonate ion.

If the Hoffman degradation is carried in absence of water an isocyanate is actually isolated.


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* When the migrating group is aryl the rate of degradation is increased by the presence of electronreleasing substituents in the aromatic ring. Thus substituted benzamide show the following order ofreactivity :

G : –OCH3 > –CH

3 > –H > –Cl > – NO

2

6. Gabriel Phthalimide Synthesis :

Practice Problems :

1. Boiling of C2H

5NCO + NaOH leads to the formation of

(a) C2H

5COOH + NH

3(b) C

2H

5NH

2 + Na

2CO

3

(c) CH3NH

2 + CH

3COONa (d) None

2. Intermediates of this reaction are except :

(a) R – N = C = O (b)

(c) (d) a, c

3. Which of the following would you predict as incorrect

(a) can be hydrolysed to C2H

5COOH

(b) (CN)2 can be hydrolysed to


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(c) can be hydrolysed to C2H

5NH

2 and NO

3—

(d) can be hydrolysed to C2H

5NH

2 and CH

3COOH

4. Which of the following reactions does not yield an amine

(a) ......OHNCR H2

(b) ......NHXR 3

(c) ......]H[NOHCHRNa

OHHC 52 (d) ......]H[4RCONH 4LiAlH

2

[Answers : (1) b (2) b (3) c (4) a]

C3 Chemical properties of Amines : The tendency of nitrogen to share the unpaired electronsunderlines the entire chemical behaviour of amines : their basicity, their action as nucleophiles - inboth aliphatic and acyl substitution - and the usually high reactivity of aromatic rings bearing aminoor substituted amino groups.

1. Basicity of Amines : Salt formation :

R – NH2 + H+ R+NH

3

R2NH + H+ R

2NH

2+

R3N + H+ R

3NH+

Example :

Structure and Basicity :

Let us see how basicities are related to the structure.

We shall compare the stabilities of amines with the stabilities of their ions; the more stable the ionrelative to the amine from which it is formed, the more basic the amine.

First of all, amines are more basic than alcohols, ethers, esters etc. for the same reason thatammonia is more basic than water, Nitrogen is less electronegative than oxygen and can betteraccomodate the positive charge of the ion.

An aliphatic amine is more basic than ammonia : because the electron-releasing alkyl groups tend todisperse the positive charge of the substituted ammonium ion;


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How can be account for the fact that aromatic amines are weaker bases than ammonia ?

Let us compare the structure of aniline with anilinium ion with the structures of ammonia and theammonium ion.

Aniline i.e. Aromatic amines are less basic due to the fact that amine is stablized by resonance to thegreater extent than its ion.

From another point of view we can say that its electron pair is partly shared by ring and is lessavailable for sharing with a hydrogen ion.

Effect of substituents on basicity of aromatic amines :

Electron releasing substituents like CH3, increases the basicity of aniline, and electron withdrawing

substituents like –X, –NO2 decreases the basicity.

The electron releasing substituents tends to disperse the positive charge of the anilinium ion, andthus stablizes the ion relative to amine. The electron withdrawing tends to intensify the positivecharge of the anilinium ion, and thus destablizes the ion relative to the amine.

We notice that base strengthening substituents are the ones that activate an aromatic ring towardselectrophilic substitution; the base-weakining substituents are the ones that deactivate an aromaticring towards electrophilic substitution.

2. Alkylation :

XArNRArNRArNHRArNH

XNRNRNHRRNH

3RX

2RXRX

2

4RX

3RX

2RX

2


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Example :

)4(iodideammonium

propylnTrimethyl3373

ICH3

|CH

73ICH

3

|H

73ICH

273

0

3

3

33 I)CH(NHCnCHNHCnCHNHCnNHHCn

3. Hoffmann elimination from quatenary Ammonium Salts :

Example :

This reaction is called Hoffmann elimination, is quite analogous to the dehydrohalogenation of analkyl halide. Most commonly reaction is E

2 :

Hydroxide ion abstracts a proton from carbon; a molecule of tertiary amine is expelled.

4. The Cope Elimination :

Tertiary amine oxide are prepared easily by treating tertiary amines with H2O

2.

5. Reactions of Amines with Nitrous acid :

Nitrous acid is a weak acid & is unstable also. It is prepared by treating sodium nitrite (NaNO2) with

an aqueous solution of a strong acid :

HCl (aq) + NaNO2(aq) HONO(aq) + NaCl(aq)

H2SO

4(aq) + NaNO

2(aq) HONO(aq) + Na

2SO

4(aq)


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Nitrous acid reacts with all kinds of amines. The products that we obtain from these reactionsdepends on whether the amine is primary, secondary or tertiary and whether the amine is aliphaticor aromatic.

Reactions of primary aliphatic amines with nitrous acid :

Primary aliphatic amines react with nitrous acid through diazotisation reaction giving high yield ofunstable diazonium salts.

Even at low temperature they decompose to form nitrogen (N2) and carbocation (R+)

R+ reacts with H2O to form ROH, or alkene or R – X. It means mixture of products produced.

Reactions of Primary Arylamines with Nitrous acid :

Primary arylamine react with HONO acid to give arenediazonium salts. These salts are althoughunstable but are more stable than the diazonium salt of aliphatic primary amine.

X:NNArArNH

C50Temp.

OHHONO,

arylaminePrimary2 0

2

Reaction of Secondary amine with Nitrous acid :

Secondary amines both aliphatic and aromic react with nitrous acid to yeild N-nitroamines usuallyseparate from reaction mixture as oily yellow liquid. Specific Examples :

oil)yellow(aamineethylNitrosodimN

23OH

HONO2

..

23 NON)(CHNaNOHClHN)(CH2

Reaction of Tertiary amine with nitrous acid :

When tertiary aliphatic amine is mixed with nitrous acid an equilibrium is established among thetertiary amine, its salt and an N-nitrosoammonium ion compound

23 NaNOHX:NR

OXNNRHXNR..

3saltAmine

3

Tertiary aryl amine react with nitrous acid to form p-nitroso aromatic compound.

Nitrosation exclusivery takes place at para position.


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Replacement Reactions of Arene Diazonium Salts :

[H3PO

2 is known as hypophosphorous acid]

6. Ring Substitution in Aromatic Amines :

Example :

(a)

(b)

(c)


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Nitric acid not only nitrates but also oxidizes the highly reactive ring as well.

In the strongly acidic condition aniline is converted into anilinium ion (–NH3+) because of its positive

charge it directs substitution to the meta position.

To overcome this difficulty, we protect the amino group : we acetylate the amine, then carry out thesubstitution and finally hydrolyze the amide to the desired substituted amine

For Example :

(a)

(b)

7. Sulfonation of Aromatic Amines :

Sulphanilamide. The Sulfa drug :


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8. Analysis of Amines : Hinsberg Test :

reactionNoClSOHCNR

.rxnnoRNSOHCClSOHCNHR

NHRSOHCKNRSOHCNHRSOHCClSOHCNHR

25633

KOH

solutionKOHinInsoluble

|R

2562562

2

256H

SolutionClear256

KOH256256

12

0

0

0

9. Carbyl amine test : It is given by 10 alkyl amine and aryl amine.

OHKCl3RNCKOH3CHClRNH 232

unpleasent smell of alkyl isocyanide is obtained. 20 amine and 30 amine does not give this test.

Practice Problems :

1. Which compound is obtained at the end of the following reaction,

)C()B()A(Ethylamine 352 NHPClHNO

(a) ethyl cyanide (b) ethyl amine (c) methyl amine (d) acetamide

2. When ethyl amine is heated with chloroform and alcoholic KOH, a bad odour compound is formed.The compound is

(a) a secondary amine (b) an acid

(c) a cyanide (d) an isocyanide

3. CH3NH

2 + CHCl

3 + 3KOH X + Y + 3H

2O; compounds X and Y are

(a) CH3CN + 3KCl (b) CH

3NC + 2KCl

(c) CH3CONH

2 + 3KCl (d) CH

3NC + K

2CO

3

4. In the following series of reaction, A is

OHHC)B()A( 52HNOductionRe 2

(a) CH3CN (b) CH

3NC (c) C

2H

5CN (d) CH

3NO

2

5. Which one of the following is least basic

(a) C2H

5NH

2(b) NH

3(c) (C

2H

5)

2NH (d) C

6H

5NH

2

6. Which of the following is least basic

(a) aniline (b) p-methylaniline

(c) diphenylamine (d) triphenylamine

7. A positive carbylamine test is given by

(a) N, N-dimethyl aniline (b) 2, 4-dimethyl aniline

(c) N-methyl-o-methylaniline (d) p-methyl benzylamine

8. A nitrogenous substance X is treated with HNO2 and the product so formed is further treated with

NaOH solution, which produces blue colouration. X can be

(a) CH3CH

2NH

2(b) CH

3CH

2NO

2

(c) CH3CH

2ONO (d) (CH

3)

2CHNO

2


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9.

X is :

(a) (b) (CH3)

3N + CH

3 – CH = CH

2 + H

2O

(c) (CH3)

3N + CH

3CH

2CH

2OH (d)

10. OHCHNONHC 1042)x(114 (30 alcohol) hence X will give :

(a) carbyl amine reaction

(b) Hofmann mustard oil reaction

(c) diazonium salt (as the intermediate) with HNO2

(d) all are correct

11. In the following compounds,

the order of basicity is

(a) IV > I > III > II (b) III > I > IV > II

(c) II > I > III > IV (d) I > III > II > IV

12. NH2 A

OH

MgBrCH2POCl

3

33

(a) (b)

(c) (d)

[Answers : (1) b (2) d (3) b (4) a (5) d (6) d (7) b (8) d (9) b (10) d (11) d (12) a]


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INITIAL STEP EXERCISE

1. The product (D) in the following sequence ofreaction is

)B()A(COOHCH heatNH3

3

)D()C( OHHCNaOP 5252

(a) ester (b) amine

(c) acid (d) alcohol

2. Ethyl amine on oxidation with acidified KMnO4

gives

(a) an acid

(b) an alcohol

(c) an aldehyde

(d) a nitro compound

3. The correct increasing order of basic strength in,

CH3CH

2CN, CH

3CH

2NH

2, CH

3N = CHCH

3 is

(a) CH3N = CHCH

3, CH

3CH

2NH

2,

CH3CH

2CN

(b) CH3CH

2NH

2, CH

3N = CHCH

3,

CH3CH

2CN

(c) CH3CH

2CN, CH

3N = CHCH

3,

CH3CH

2NH

2

(d) CH3CH

2CN, CH

3CH

2NH

2, CH

3N =

CHCH3

4. Chlorobenzene can be prepared by reacting anilinewith

(a) HCl

(b) Cu2Cl

2

(c) Chlorine in presence of anhydrous AlCl3

(d) nitrous acid followed by heating withCu

2Cl

2

5. Nitrobenzene on reduction with Zn and NH4Cl

forms

(a) aniline

(b) nitrobenzene

(c) hydrazobenzene

(d) phenyl hydroxylamine

6. In the reaction,

)B()A(NHHCKCN

CuCN

C50

HClNaNO256 0

2

)C(OH/H 2

the product (C) is

(a) C6H

5CH

2NH

2(b) C

6H

5COOH

(c) C6H

5OH (d) none of these

7. An organic compound X having molecular formulaC

6H

7O

2N has 6 carbon atoms in a ring system, two

double bonds and also a nitro group as substitu-tion, X is

(a) homocyclic but not aromatic

(b) aromatic but not homocyclic

(c) homocyclic and aromatic

(d) heterocyclic

8. By the action of bromine and alkali on benzamideit gives

(a) benzene (b) aniline

(c) bromo benzene (d) acetanilide

9. Nitroso amines (R2N – N = O) are water

soluble. On heating with conc. HCl, they givesecondary amines. The reaction is called

(a) Perkin reaction

(b) Fries reaction

(c) Liebermann nitroso reaction

(d) Etard reaction

10. Which nitro compound will show tautomerism

(a) C6H

5NO

2(b) (CH

3)

3CNO

2

(c) CH3CH

2NO

2(d) o-nitrotoluene

11. HCONHR 3POCl

Pyridine ? is

(a) RCN (b) RNC

(c) RCNO (d) RNCO

12. Identify X in the series,

42

3

SOH

HNO intermediate

OH2 X

(a) (b)

(c) (d)


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FINAL STEP EXERCISE

1. A compound A when reacted with PCl5 and then

with ammonia gave B, B when treated withbromine and cuastic potash produced C. C ontreatment with NaNO

2 and HCl at 00C and then

boiling produced orthocresol. Compound A is(a) o-toluic acid(b) o-chlorotoluene(c) o-bromotoluene(d) m-toluic acid

2. An aromatic amine (A) was treated with alcoholicpotash and another compound (Y) when a foulsmelling gas was formed with formula C

6H

5NC. (Y)

was formed by reacting a compound (Z) with Cl2

in presence of slaked lime. Compound (Z) is(a) C

6H

5NH

2(b) CH

3OH

(c) CH3COCH

3(d) CHCl

3

3. Deamination of n-BuNH2 with NaNO

3/HCl gives

two butanols, two butenes and two butyl chlorides.The possible explanation of these products is

(a) Intermediate formed is RN2+ which is

very stable(b) As intermediate is carbocation(c) Both (a) and (b)(d) None

4. What products would you expect to get by theapplication of the Hofmann exhaustive methylationto Me

2CHCH

2CH

2NH

2

(a) Me2C = CH

2

(b) Me2HCCH = CH

2

(c) CH2 = CH

2

(d) All5. An organic compound (A) on reduction gave a

compound (B). Upon treatment with HNO2, (B)

gave ethyl alcohol and on warming with CHCl3 and

alcoholic KOH, (A) gave offensive smell. Thecompound (A) is(a) CH

3CN (b) C

2H

5CN

(c) CH3NH

2(d) CH

3NC

13. The reactions,

RI

2OH2 RNH2

illustrate :

(a) Gabriel’s phthalimide reaction

(b) A good method to prepare pure secondary amine

(c) A reaction which can be extended topreparation of -amino acid

(d) None

14. Hinsberg reagent is.................and reactswith....................amine to form a product soluble inalkali :

(a) — SO2Cl, 10

(b) —SO2NH

2, 20

(c) HO— —CH3, 30

(d) —SO2Cl, 20

15.

Which is correct alternate ?

(a)

(b)

(c)

(d) none is correct


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6. Examine the following two structures for theanilinium ion and choose the correct statementfrom the ones give below :

(a) II is not an acceptable canonicalstructure because carbonium ions are lessstable than ammonium ions

(b) II is not an accepted canonical structurebecause it is non-aromatic

(c) II is not an acceptable canonicalstructure because the nitrogen has 10valence electrons

(d) II is an acceptable canonical structure7. What major products would you expect to get by

the application of the Hofmann exhaustivemethylation respectivelyMe

2CHCH

2NHCH

2CH

2Me; EtNHCH

2CH

2Cl

(A) (B)(a) Me

2C = CH

2, CH

2 = CH

2

(b) MeCH = CH2, CH

2 = CH

2

(c) MeCH = CH2, CH

2 = CHCl

(d) Me2C = CH

2, CH

2 = CHCl

8. A compound X has the molecular formula C7H

7NO.

On treatment with Br2 and KOH, X gives an amine

Y. The latter gives carbylamine test. Y upondiazotisation and coupling with phenol gives an azodye. Thus X is(a) C

6H

5CONH

2(b) C

6H

5NO

2

(c) C6H

5COONH

4(d) None

9. Methyl ethyl propylamine formsnon-super-imposable mirror images but it does notshow optical activity because(a) Of rapid flipping(b) Amines are basic in nature(c) Nitrogen has a lone pair of electrons(d) Of absence of asymmetric nitrogen

10. Which is maximum basic in nature ?

(a)

(b)

(c)

(d)

11. End product of following sequence of reaction :

— Br CBA BaOOH/ONH 233

(a) = O

(b) —OH

(c) = O

(d)

ANSWERS (INITIAL STEPEXERCISE)

9. c

10. c

11. b

12. b

13. a

14. a

15. a

1. b

2. c

3. c

4. d

5. d

6. b

7. a

8. b

ANSWERS (FINAL STEP EXERCISE)

1. a

2. c

3. b

4. b

5. a

6. c

7. c

8. a

9. a

10. b

11. c


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AIEEE ANALYSIS [2004/2005]

AIEEE ANALYSIS [2003]

2. Ethyl isocyanide on hydrolysis in acidic mediumgenerates

(a) methylamine salt and ethanoic acid

(b) ethylamine salt and methanol acid

(c) propanoic acid and ammonium salt

(d) ethanoic acid and ammonium salt

4. The ammonia evolved from the treatment of 0.30of an organic compound for the estimation ofnitrogen was passed in 100 mL of 0.1 M sulphuricacid. The excess of acid required 20 mL of 0.5 Msodium hydroxide solution for completeneutralization. The organic compound is

(a) acetamide (b) benzamide

(c) urea (d) thiourea

[2004]

5. Which of the following is the strongest base ?

(a)

(b)

(c)

(d)

[2004]

6. Which one of the following methods is neithermeant for the synthesis nor for separation of amines?

(a) Hinsberg method

(b) Hofmann method

(c) Wurtz reaction

(d) Curtius reaction

[2005]

7. An organic compound having molecular mass 60 isfound to contain C = 20%, H = 6.67% andN = 46.67% while rest is oxygen. On heating it givesNH

3 alongwith a solid residue. The solid residue give

violet colour with alkaline copper sulphate solution,the compound is

(a) CH3NCO

(b) CH3CONH

2

(c) (NH2)

2CO

(d) CH3CH

2CONH

2

[2005]


1. When primary amine reacts with chloroform inethanoic KOH then the product is

(a) an alcohol (b) a cyanide

(c) an aldehyde (d) an isocyanide

3. The reaction of chloroform with a alcoholic KOHand p-toluidine forms

(a)

(b)

(c)

(d)

ANSWERS AIEEE ANALYSIS

1. d 2. a 3. a 4. c 5. d 6. c 7. c


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1. Regular use of which of the following fertilizersincreases the acidity of soil ?(a) Superphosphate of lime(b) Ammonium sulphate(c) Potassium nitrate(d) Urea[Ans. : b]

2. Which one of the following is the strongest base inaqueous solution ?(a) Dimethylamine(b) Methylamine(c) Trimethylamine(d) Aniline[Ans. : a]

3. In the chemical reaction,CH

3CH

2NH

2 + CHCl

3 + 3KOH (A) + (B) + 3H

2O,

the compound (A) and (B) are respectively :(a) C

2H

5NC and K

2CO

3

(b) C2H

5NC and 2KCl

(c) C2H

5CN and 3KCl

(d) CH3CH

2CONH

2 and 3KCl

[Ans. : b]

TEST YOURSELF

1. Reaction NaOBr

23CONHCH gives

(a) CH3Br (b) CH

4

(c) CH3OBr (d) CH

3NH

3

2. Hoffmann bromamide reaction is used to prepare.Which degree of amine from amides(a) 10 (b) 20

(c) 30 (d) all3. Primary amines give

(a) Iodoform test(b) Victor mayer test(c) Lucas test(d) Carbylamine test

4. is a

(a) primary amine(b) secondary amine(c) tertiary amine(d) quaternary salt

5. A positive carbylamine test is given by(a) N, N dimethylaniline(b) 2, 4-dimethylaniline(c) N-methyl-o-methylaniline(d) P-methylbenzylamine

6. How many primary amines are possible for theformula C

4H

11N

(a) 1 (b) 2(c) 3 (d) 4

7. Resonance hybrid of nitrate ion is

(a)

(b)

(c)

(d)

8. An organic compound having molecular mass 60 isfound to contain C = 20%, H = 6.67 % andN = 46.67 % while rest is oxygen. On heating it givesNH

3 alongwith a solid residue. The solid residue

gives violet colour with alkaline copper sulphatesolution. The compound is(a) CH

3NCO

(b) CH3CONH

2

(c) (NH2)

2CO

(d) CH3CH

2CONH

2

9. The correct order of basicities of the followingcompounds is

(a) 2 > 1 > 3 > 4 (b) 1 > 3 > 2 > 4(c) 3 > 1 > 2 > 4 (d) 1 > 2 > 3 > 4

10. Which of the following carbocations is expected tobe most stable ?

(a) (b)

(c) (d)

ANSWERS

1. d

2. a 6. d

3. d

4. a

5. d 7. c

8. c

9. b

10. d

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ORGANIC COMPOUND CONTAINING NITROGEN - …einsteinclasses.com/JEE Main Website/Chemistry/Or_Co_C_Nit.pdf · ORGANIC COMPOUND CONTAINING NITROGEN ... Aliphatic amines are named by