Chapter-13 Amines

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  • Chapter-13 Amines Assignments 1

    A colourless substance ‘A’ (C6H7N) is sparingly soluble in water and gives a
    water soluble compound ‘B’ on treating with mineral acid. On reacting with
    CHCl3 and alcoholic potash ‘A’ produces an obnoxious smell due to the
    formation of compound ‘C’. Reaction of ‘A’ with benzenesulphonyl chloride
    gives compound ‘D’ which is soluble in alkali. With NaNO2 and HCl, ‘A’ forms
    compound ‘E’ which reacts with phenol in alkaline medium to give an orange
    dye ‘F’. Identify compounds ‘A’ to ‘F’.

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  • Chapter-13 Amines Assignments 2

    A hydrocarbon ‘A’, (C4H8) on reaction with HCl gives a compound ‘B’, (C4H9Cl),
    which on reaction with 1 mol of NH3 gives compound ‘C’, (C4H11N). On reacting
    with NaNO2 and HCl followed by treatment with water, compound ‘C’ yields
    an optically active alcohol, ‘D’. Ozonolysis of ‘A’ gives 2 mols of acetaldehyde.
    Identify compounds ‘A’ to ‘D’. Explain the reactions involved.

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  • Chapter-13 Amines Assignments 3

    A solution contains 1 g mol. each of p-toluene diazonium chloride and pnitrophenyl
    diazonium chloride. To this 1 g mol. of alkaline solution of phenol
    is added. Predict the major product. Explain your answer.

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  • Chapter-13 Amines Assignments 4

    Write following conversions:
    (i) nitrobenzene ⎯→ acetanilide (ii) acetanilide ⎯→ p-nitroaniline

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  • Chapter-13 Amines Assignments 5

    How will you carry out the following conversions?
    (i) toluene ⎯⎯⎯→ p-toluidine
    (ii) p-toluidine diazonium chloride ⎯⎯⎯→ p-toluic acid

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  • Chapter-13 Amines Assignments 6

    Why is aniline soluble in aqueous HCl?

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  • Chapter-13 Amines Assignments 7

    What is the structure and IUPAC name of the compound, allyl amine?

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  • Chapter-13 Amines Assignments 8

    Predict the product of reaction of aniline with bromine in non-polar solvent
    such as CS2.

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  • Chapter-13 Amines Assignments 9

    Under what reaction conditions (acidic/basic), the coupling reaction of
    aryldiazonium chloride with aniline is carried out?

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  • Chapter-13 Amines Assignments 10

    What is the role of pyridine in the acylation reaction of amines?

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  • Chapter-13 Amines Assignments 11

    Explain why MeNH2 is stronger base than MeOH?

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  • Chapter-13 Amines Assignments 12

    Why does acetylation of —NH2 group of aniline reduce its activating effect?

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  • Chapter-13 Amines Assignments 13

    Why is benzene diazonium chloride not stored and is used immediately after
    its preparation?

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  • Chapter-13 Amines Assignments 14

    What is Hinsberg reagent?

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  • Chapter-13 Amines Assignments 15

    What is the best reagent to convert nitrile to primary amine?

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  • Chapter-13 Amines Assignments 16

    What is the product when C6H5CH2NH2 reacts with HNO2?

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  • Chapter-13 Amines Assignments 17

    Why is NH2 group of aniline acetylated before carrying out nitration?

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  • Chapter-13 Amines Assignments 18

    What is the role of HNO3 in the nitrating mixture used for nitration of benzene?

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  • Chapter-13 Amines Assignments 19

    Account for the following:

     

    (i) pKb of aniline is more than that of methylamine.

    (ii) Ethylamine is soluble in water whereas aniline is not.

    (iii) Methylamine in water reacts with ferric chloride to precipitate hydrated ferric oxide. (iv) Although amino group is o– and p– directing in aromatic electrophilic

    substitution reactions, aniline on nitration gives a substantial amount of m-nitroaniline.

    (v) Aniline does not undergo Friedel-Crafts reaction.

    (vi) Diazonium salts of aromatic amines are more stable than those of aliphatic amines.

    (vii) Gabriel phthalimide synthesis is preferred for synthesising primary amines.

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  • Chapter-13 Amines Assignments 20

    Why cannot aromatic primary amines be prepared by Gabriel phthalimide

     

    synthesis?

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  • Chapter-13 Amines Assignments 21

    Give plausible 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 point than tertiary amines?

    (iii) Why are aliphatic amines stronger bases than aromatic amines?

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  • Chapter-13 Amines Assignments 22

    Give the IUPAC name of the compound and classify into primary, secondary or

    tertiary amines.

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  • Chapter-13 Amines Assignments 23

    Give the IUPAC name of the compound and classify into primary, secondary or tertiary amines.

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  • Chapter-13 Amines Assignments 24

    Give the IUPAC name of the compound and classify into primary, secondary or tertiary amines.

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  • Chapter-13 Amines Assignments 25

    Write short notes on diazotization

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  • Chapter-13 Amines Assignments 26

    Write short notes on ammonolysis

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  • Chapter-13 Amines Assignments 27

    Write short notes on acetylation.

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  • Chapter-13 Amines Assignments 28

    Why are amines basic in character?

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  • Chapter-13 Amines Assignments 29

    Write chemical equations for the following reactions

    (i) Reaction of ethanolic NH3  with C2H5Cl.

    (ii) Ammonolysis of benzyl chloride and reaction of amine so formed with two moles of CH3Cl

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  • Chapter-13 Amines Assignments 30

    Write chemical equations for the following conversions:

    (i) CH3  –CH2  –Cl into CH3 –CH2  –CH2  –NH2

    (ii) C6H5–CH5 –Cl into C6H5  –CH2  –CH2  –NH2

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  • Chapter-13 Amines Assignments 31

    Write structures and IUPAC names of

     

    (i) the amide which gives propanamine by Hoffmann bromamide reaction.

    (ii) the amine produced by the Hoffmann degradation of benzamide.

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  • Chapter-13 Amines Assignments 32

    How will you convert 4-nitrotoluene to 2-bromobenzoic acid?

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  • Chapter-13 Amines Assignments 33

    Write the reactions of (i) aromatic and (ii) aliphatic primary amines with nitrous acid.

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  • Chapter-13 Amines Assignments 34

    How will you convert:

     

    (i) Ethanoic acid into methanamine

    (ii) Hexanenitrile into 1-aminopentane

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  • Chapter-13 Amines Assignments 35

    How will you convert:

     

    (i) Methanol to ethanoic acid

    (ii) Ethanamine into methanamine

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  • Chapter-13 Amines Assignments 36

    How will you convert

     

    (i ) Ethanoic acid into propanoic acid

    (ii) Methanamine into ethanamine

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  • Chapter-13 Amines Assignments 37

    How will you convert

     

    (i) Nitromethane into dimethylamine

     

    (ii) Propanoic acid into ethanoic acid?

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  • Chapter-13 Amines Assignments 38

    An  aromatic  compound ‗A‘  on  treatment with  aqueous  ammonia and  heating  forms compound ‗B‘ which on heating with Br2  and KOH forms a compound ‗C‘ of molecular formula C6H7N. Write the structures and IUPAC names of compounds A, B and C.

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  • Chapter-13 Amines Assignments 39

    Arrange the following:

     

    (i)         In decreasing order of the pKb values:

    C2H5  NH2, C6H5NHCH3, (C2H5)2  NH and C6H5NH2

     

    (ii) In increasing order of basic strength:

     

    C6H5NH2, C6H5N(CH3)2  , (C2H5)2  NH and CH3NH2

     

    (iii) In increasing order of basic strength: Aniline, p-nitroaniline and p-toluidine

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  • Chapter-13 Amines Assignments 40

    Arrange the following

    (i) In decreasing order of basic strength in gas phase: C2H5NH2, (C2H5)2NH, (C2H5)3N and NH3

    (ii) In increasing order of boiling point:

    C2H5OH, (CH3)2NH, C2H5NH2

    (iii) In increasing order of solubility in water: C6H5NH2, (C2H5)2NH, C2H5NH2.

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  • Chapter-13 Amines Assignments 41

    Accomplish the following conversions: (i) Nitrobenzene to benzoic acid

    (ii) Benzene to m-bromophenol

    (iii) Benzoic acid to aniline

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  • Chapter-13 Amines Assignments 42

    Accomplish the following conversions:

    (i) Aniline to 2,4,6-tribromofluorobenzene

    (ii) Benzyl chloride to 2-phenylethanamine

    (iii) Chlorobenzene to p-chloroaniline

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  • Chapter-13 Amines Assignments 43

    Accomplish the following conversions: (i) Aniline to p-bromoaniline

    (ii) Benzamide to toluene

    (iii) Aniline to benzyl alcohol. 

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  • Chapter-13 Amines Assignments 44

    Write the reactions of (i) aromatic and (ii) aliphatic primary amines with nitrous acid.

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  • Chapter-13 Amines Assignments 45

    Why cannot aromatic primary amines be prepared by Gabriel phthalimide synthesis?

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  • Chapter-13 Amines Assignments 46

    Complete the following reactions:

    (i) 

    (ii) 

    (iii) 

    (iv) 

    (v) 

    (vi) 

    (vii) 

     

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  • Chapter-13 Amines Assignments 47

    An aromatic compound 'A' on treatment with aqueous ammonia and heating

    forms compound 'B' which on heating with Br2 and KOH forms a compound 'C'

    of molecular formula C6H7N. Write the structures and IUPAC names of compounds A, B and C.

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  • Chapter-13 Amines Assignments 48

    Give the structures of A, B and C in the following reactions:

    (i) 

    (ii) 

    (iii) 

    (iv) 

    (v) 

    (vi) 

     

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  • Chapter-13 Amines Assignments 49

    Accomplish the following conversions:

    (i) Nitrobenzene to benzoic acid

    (ii) Benzene to m-bromophenol

    (iii) Benzoic acid to aniline

    (iv) Aniline to 2,4,6-tribromofluorobenzene

    (v) Benzyl chloride to 2-phenylethanamine

    (vi) Chlorobenzene to p-chloroaniline

    (vii) Aniline to p-bromoaniline

    (viii) Benzamide to toluene

    (ix) Aniline to benzyl alcohol.

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  • Chapter-13 Amines Assignments 50

    Write short notes on the following:

    (i) Carbylamine reaction (ii) Diazotisation

    (iii) Hofmann's bromamide reaction (iv) Coupling reaction

    (v) Ammonolysis (vi) Acetylation

    (vii) Gabriel phthalimide synthesis.

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  • Chapter-13 Amines Assignments 51

    Describe a method for the identification of primary, secondary and tertiary amines. Also write chemical equations of the reactions involved.

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  • Chapter-13 Amines Assignments 52

    How will you convert:

    (i) Ethanoic acid into methanamine

    (ii) Hexanenitrile into 1-aminopentane

    (iii) Methanol to ethanoic acid

    (iv) Ethanamine into methanamine

    (v) Ethanoic acid into propanoic acid

    (vi) Methanamine into ethanamine

    (vii) Nitromethane into dimethylamine

    (viii) Propanoic acid into ethanoic acid

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  • Chapter-13 Amines Assignments 53

    Arrange the following:

    (i) In decreasing order of the pKbvalues:

    C2H5NH2, C6H5NHCH3, (C2H5)2NH and C6H5NH2

    (ii) In increasing order of basic strength:

    C6H5NH2, C6H5N(CH3)2, (C2H5)2NH and CH3NH2

    (iii) In increasing order of basic strength:

    (a) Aniline, p-nitroaniline and p-toluidine

    (b) C6H5NH2, C6H5NHCH3, C6H5CH2NH2.

    (iv) In decreasing order of basic strength in gas phase:

    C2H5NH2, (C2H5)2NH, (C2H5)3N and NH3

    (v) In increasing order of boiling point:

    C2H5OH, (CH3)2NH, C2H5NH2

    (vi) In increasing order of solubility in water:

    C6H5NH2, (C2H5)2NH, C2H5NH2.

     

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  • Chapter-13 Amines Assignments 54

    Account for the following:

    (i) pKb of aniline is more than that of methylamine.

    (ii) Ethylamine is soluble in water whereas aniline is not.

    (iii) Methylamine in water reacts with ferric chloride to precipitate hydrated ferric oxide.

    (iv) Although amino group is o, p- directing in aromatic electrophilic substitution reactions, aniline on nitration gives a substantial amount of m-nitroaniline.

    (v) Aniline does not undergo Friedel-Crafts reaction.

    (vi) Diazonium salts of aromatic amines are more stable than those of aliphatic amines.

    (vii) Gabriel phthalimide synthesis is preferred for synthesising primary amines.

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  • Chapter-13 Amines Assignments 55

    Write IUPAC names of the following compounds and classify them into primary,

    secondary and tertiary amines.

    (i) (CH3)2 CHNH2 (ii) CH3(CH2)2NH2

    (iii) CH3NHCH(CH3)2 (iv) (CH3)3CNH2

    (v) C6H5NHCH3 (vi) (CH3CH2)2NCH3

    (vii) m-BrC6H4NH2

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  • Chapter-13 Amines Assignments 56

    Convert

    (i) 3-Methylaniline into 3-nitrotoluene.

    (ii) Aniline into 1,3,5-tribromobenzene.

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  • Chapter-13 Amines Assignments 57

    Write structures of different isomers corresponding to the molecular formula,

    C3H9N. Write IUPAC names of the isomers which will liberate nitrogen gas on

    treatment with nitrous acid.

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  • Chapter-13 Amines Assignments 58

    Write chemical reaction of aniline with benzoyl chloride and write the name of

    the product obtained.

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  • Chapter-13 Amines Assignments 59

    Write reactions of the final alkylation product of aniline with excess of methyl

    iodide in the presence of sodium carbonate solution.

     

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  • Chapter-13 Amines Assignments 60

    Complete the following acid-base reactions and name the products:

    (i) CH3CH2CH2NH2 + HCl 

    (ii) (C2H5)3N + HCl 

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  • Chapter-13 Amines Assignments 61

    Arrange the following in increasing order of their basic strength:

    (i) C2H5NH2, C6H5NH2, NH3, C6H5CH2NH2 and (C2H5)2NH

    (ii) C2H5NH2, (C2H5)2NH, (C2H5)3N, C6H5NH2

    (iii) CH3NH2, (CH3)2NH, (CH3)3N, C6H5NH2, C6H5CH2NH2.

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  • Chapter-13 Amines Assignments 62

    How will you convert?

    (i) Benzene into aniline

    (ii) Benzene into N, N-dimethylaniline

    (iii) Cl-(CH2)4-Cl into hexan-1, 6-diamine?

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  • Chapter-13 Amines Assignments 63

    Classify the following amines as primary, secondary or tertiary:

    (i)

    (ii)

    (iii) (C2H5)2CHNH2

    (iv) (C2H5)2NH

     

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  • Chapter-13 Amines Assignments 64

    (i) Write structures of different isomeric amines corresponding to the molecular formula, C4H11N

    (ii) Write IUPAC names of all the isomers.

    (iii) What type of isomerism is exhibited by different pairs of amines?

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