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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
What is the temperature for mononitration during acid base reaction?
10-degree Celsius
26
What is Heinsberg's test?
It is used to distinguish among 1°, 2°, 3° Amines.
27
Heinsberg's reagent
Benzenesulphonyl chloride
28
How do we distinguish between amines through Heinsberg's test?
1° amines give soluble product, a salt. 2° amines give insoluble product 3° amines do not give product.
29
Which amines give carbylamine reaction?
1° aliphatic and aromatic
30
Reagents of carbylamine reaction
CHCl₃ + KOH (ethanolic)
31
Products of carbylamine reaction
RNC + 3KCl + 3H₂O
32
RNC compounds name and property
Named as isocyanides and they are foul smelling.
33
:CCl₂ is
Dichlorocarbene an electrophile
34
Hoffmann mustard oil reaction
test for 1° amines reagent- 1.) CS₂ 2.) HgCl₂
34
Product of Hoffmann mustard oil reaction with reactant (CH₃-CH₂-NH₂) Ethylamine + CS₂
CH₃-CH₂-N=C=S (ethyl isothiocyanate) which smells like mustard oil
35
Which one is more basic? Cyclic amines or open chain amines
Cyclic amines are slightly more basic than open chain amines.
36
3° amines are
non- resolvable i.e., cannot be separated to give pure enantiomers, due to amine inversion
37
Of which hybridization N shows inversion
All sp³
38
Amine Inversion α
Steric hindrance (bulky groups) and 1/EN of boundary atoms
39
What is Nucleophilic acyl substitution reaction?
The reaction of an acid chloride/ anhydride with 1° or 2° amines to give substituted amides.
40
1° Aliphatic Amine with HNO₂ at low temperature gives
clear solution (ROH) with evolution of N₂ gas.
41
2° Aliphatic Amine with HNO₂ gives
insoluble yellow oily liquid (R₂N-N=O) N-nitrosamine
42
3° Aliphatic Amine with HNO₂ gives
clear solution (ammonium salt)
43
Why does diazotization of 1° aliphatic amines considered a bad reaction?
Because it leads to a mixture of product.
44
1° Aromatic Amine with HNO₂ gives
Gives Diazonium cation (resonance stabilized)
45
2° Aromatic Amine with HNO₂ gives
Insoluble yellow oily liquid
46
3° Aromatic Amine with HNO₂ gives
o- and p- substituted nitrosoaniline
47
Diazonium ion on reaction with 1). HBF₄ 2). NaNO₂, Cu, with heat gives
Nitrobenzene
48
Diazonium ion on reaction with H₃PO₂ gives
Benzene + H₃PO₃
49
Diazonium ion on reaction with CH₃CH₂OH gives
Benzene + CH₃CHO + Benzene ethoxide (by product)
50
Diazonium cation couples only with
strongly activated benzene rings, e.g., Phenols, anilines, naphthol, etc. because diazonium ion itself is a weak electrophile.
51
Why does coupling occurs at para position?
due to steric hindrance at ortho
52
when does coupling reaction occur at ortho?
when para position is occupied
53
why are products of coupling reaction called dyes?
they are colored due to extended conjugation
54
In which medium does coupling of phenols occur?
Slightly alkaline medium
55
Why does phenol ionize to phenoxide?
Because phenoxide is more reactive.
56
What is formed in strongly alkaline medium when OH⁻ attacks as Nu: ?
Diazotate (Ph-N=N-O⁻)
57
Why coupling does not occur with aniline in strongly acidic medium?
because aniline gets protonated to anilinium ion (C6H5NH3+)
58
Organol brown and orange red dye are formed by
Diazonium ion + naphthol 2- or β-naphthol gives orange red 1- or 2- naphthol gives organol brown
59
How is methyl red formed
Anthranilic acid reacted with 1). HNO₂ 2). N,N- dimethylamine
60
When benzenediazonium chloride is heated with fluoroboric acid, fluorobenzene is formed. The reaction is called -
Balz Schiemann reaction
61
The product formed by a reaction of an aldehyde with a primary amine is
Schiff's base
62
The conversion of benzene diazonium chloride to bromobenzene can be accomplished by
Gattermann reaction
63
Condition of coupling with aniline
pH : 4-5 (not strongly acidic)
64
Nitration of chlorobenzene give
2-chloronitrobenzene and 4-chloronitrobenzene
65
Benzenediazonium chloride is converted to phenol by
warming with water

Chemistry (9 decks)

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