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Chemistry > Amines > Flashcards

Amines Flashcards

1
Q

Hofmann ammonolysis reagents

A

1). Ethanolic NH3
2). NaOH

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2
Q

Hofmann ammonolysis follows

A

Sn2 mechanism

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3
Q

Reactivity order of Hofmann ammonolysis

A

primary > secondary > tertiary
RI > RBr> RCl

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4
Q

Gabriel Phthalimide Synthesis used to prepare

A

primary aliphatic amines

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5
Q

Hoffmann exhaustive methylation

A

Amine is reacted with CH3I

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6
Q

Physical properties of lower aliphatic amines

A

they are gases with fishy odour and soluble in water due to H-bonding.

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7
Q

Physical properties of primary amines with 3 or more carbon atoms

A

they are liquid and still higher ones are solid.

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8
Q

Physical properties of aniline and other arylamines

A

they are usually colorless but get colored on storage due to atmospheric oxidation

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9
Q

The boiling point and solubility in water of Amines is lower than

A

those of alcohols of similar molar mass due to weaker H- bonding in Amines.

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10
Q

The order of bp of isomeric amines

A

1°>2°>3°

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11
Q

Electrophilic aromatic substitution (SEAr) is

A

Electrophilic aromatic substitution (SEAr) is an organic reaction in which an atom that is attached to an aromatic system (usually hydrogen) is replaced by an electrophile.

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12
Q

In bromination of Aniline what is the reagent?

A

Bromine water (3 eq. of Br2) , And forms 2,4,6 - tribromoaniline

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13
Q

color of 2,4,6 - tribromoaniline

A

white ppt

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14
Q

what is the reagent for monobromination

A

Acetic anhydride (CH3CO)2O and a (base) pyridine

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15
Q

Solvent used in monobromination is

A

Br2, CH2COOH (solvent)

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16
Q

3rd step for monobromination

A

hydrolyses

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17
Q

Nature of aniline

A

basic

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18
Q

How does nitration of aniline occur?

A

Aniline is reacted with acidic (HNO₃ + H₂SO₄)

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19
Q

Ratio of Nitration products — o-, m-, p-

A

2:47:51 %

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20
Q

when is Anilinium ion is formed

A

When acid base reaction occure between aniline and (HNO₃ + H₂SO₄)

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21
Q

Process of sulphonation of aniline

A

1). H₂SO₄
After the formation of salt
2). Heat at temp. 453-473K

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22
Q

Use of Sulphonilic acid

A

Used in making dyes

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23
Q

Sulphonilic acid resonate as

A

Zwitter ion (positive and negative charges in a molecule)

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24
Q

Why does Aniline do not show Friedel Crafts reactions?

A

Aniline gets deactivated due to salt formation.

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25
Q

What is the temperature for mononitration during acid base reaction?

A

10-degree Celsius

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26
Q

What is Heinsberg’s test?

A

It is used to distinguish among 1°, 2°, 3° Amines.

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27
Q

Heinsberg’s reagent

A

Benzenesulphonyl chloride

28
Q

How do we distinguish between amines through Heinsberg’s test?

A

1° amines give soluble product, a salt.
2° amines give insoluble product
3° amines do not give product.

29
Q

Which amines give carbylamine reaction?

A

1° aliphatic and aromatic

30
Q

Reagents of carbylamine reaction

A

CHCl₃ + KOH (ethanolic)

31
Q

Products of carbylamine reaction

A

RNC + 3KCl + 3H₂O

32
Q

RNC compounds name and property

A

Named as isocyanides and they are foul smelling.

33
Q

:CCl₂ is

A

Dichlorocarbene an electrophile

34
Q

Hoffmann mustard oil reaction

A

test for 1° amines
reagent-
1.) CS₂
2.) HgCl₂

34
Q

Product of Hoffmann mustard oil reaction with reactant (CH₃-CH₂-NH₂) Ethylamine + CS₂

A

CH₃-CH₂-N=C=S (ethyl isothiocyanate) which smells like mustard oil

35
Q

Which one is more basic? Cyclic amines or open chain amines

A

Cyclic amines are slightly more basic than open chain amines.

36
Q

3° amines are

A

non- resolvable i.e., cannot be separated to give pure enantiomers, due to amine inversion

37
Q

Of which hybridization N shows inversion

A

All sp³

38
Q

Amine Inversion α

A

Steric hindrance (bulky groups)
and
1/EN of boundary atoms

39
Q

What is Nucleophilic acyl substitution reaction?

A

The reaction of an acid chloride/ anhydride with 1° or 2° amines to give substituted amides.

40
Q

1° Aliphatic Amine with HNO₂ at low temperature gives

A

clear solution (ROH) with evolution of N₂ gas.

41
Q

2° Aliphatic Amine with HNO₂ gives

A

insoluble yellow oily liquid (R₂N-N=O) N-nitrosamine

42
Q

3° Aliphatic Amine with HNO₂ gives

A

clear solution (ammonium salt)

43
Q

Why does diazotization of 1° aliphatic amines considered a bad reaction?

A

Because it leads to a mixture of product.

44
Q

1° Aromatic Amine with HNO₂ gives

A

Gives Diazonium cation (resonance stabilized)

45
Q

2° Aromatic Amine with HNO₂ gives

A

Insoluble yellow oily liquid

46
Q

3° Aromatic Amine with HNO₂ gives

A

o- and p- substituted nitrosoaniline

47
Q

Diazonium ion on reaction with
1). HBF₄ 2). NaNO₂, Cu, with heat
gives

A

Nitrobenzene

48
Q

Diazonium ion on reaction with H₃PO₂ gives

A

Benzene + H₃PO₃

49
Q

Diazonium ion on reaction with CH₃CH₂OH gives

A

Benzene + CH₃CHO + Benzene ethoxide (by product)

50
Q

Diazonium cation couples only with

A

strongly activated benzene rings, e.g., Phenols, anilines, naphthol, etc. because diazonium ion itself is a weak electrophile.

51
Q

Why does coupling occurs at para position?

A

due to steric hindrance at ortho

52
Q

when does coupling reaction occur at ortho?

A

when para position is occupied

53
Q

why are products of coupling reaction called dyes?

A

they are colored due to extended conjugation

54
Q

In which medium does coupling of phenols occur?

A

Slightly alkaline medium

55
Q

Why does phenol ionize to phenoxide?

A

Because phenoxide is more reactive.

56
Q

What is formed in strongly alkaline medium when OH⁻ attacks as Nu: ?

A

Diazotate (Ph-N=N-O⁻)

57
Q

Why coupling does not occur with aniline in strongly acidic medium?

A

because aniline gets protonated to anilinium ion (C6H5NH3+)

58
Q

Organol brown and orange red dye are formed by

A

Diazonium ion + naphthol
2- or β-naphthol gives orange red

1- or 2- naphthol gives organol brown

59
Q

How is methyl red formed

A

Anthranilic acid reacted with 1). HNO₂
2). N,N- dimethylamine

60
Q

When benzenediazonium chloride is heated with fluoroboric acid, fluorobenzene is formed. The reaction is called -

A

Balz Schiemann reaction

61
Q

The product formed by a reaction of an aldehyde with a primary amine is

A

Schiff’s base

62
Q

The conversion of benzene diazonium chloride to bromobenzene can be accomplished by

A

Gattermann reaction

63
Q

Condition of coupling with aniline

A

pH : 4-5 (not strongly acidic)

64
Q

Nitration of chlorobenzene give

A

2-chloronitrobenzene and 4-chloronitrobenzene

65
Q

Benzenediazonium chloride is converted to phenol by

A

warming with water

Chemistry (6 decks)

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