18B Organic Nitrogen Flashcards

(33 cards)

1
Q

what is functional group for amines?

A

R-NH2

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2
Q

what is the functional group for amides?

A

R-C=ONH2

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3
Q

de-esterification of esters

A

r - NH3 (aq)
c - reflux
p - amide

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4
Q

nucleophilic addition of acyl chlorides

A

r - NH3 (aq) or conc. HCl
c - room temp
p - amide

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5
Q

dehydration of carboxylic acids

A

r - NH3 (aq)
c - reflux
p - amide

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6
Q

hydrolysis of amides

A

r - HCl (aq) or H2SO4 (aq)
c - reflux
p - carboxylic acid

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7
Q

dehydration of amides

A

r - P4O10
c - reflux
p - nitrile

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8
Q

hydrolysis of nitriles

A

r - HCl (aq) or NaOH (aq)
c - reflux
p - amide

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9
Q

hoffman degradation of amides

A

r - Br2, NaOH (aq)
c - reflux
p - amine

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10
Q

nucleophilic addition of amines

A

r - acylchloride
c - reflux
p - secondary amide

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11
Q

nucleophilic substitution of halogenoalkanes (Sn) to form amines

A

r - conc. NH3 in ethanol
c - heat in a sealed tube
p - amine

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12
Q

reduction of nitriles

A

r - LiAlH4
c - dry ether, reflux
p - amine

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13
Q

neutralisation of amines

A

r - HCl (aq) or H+ (aq)
c - room temp
p - R-NH3+Cl-

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14
Q

acylation of amines

A

r - RCOCl
c - room temp
p - secondary amide

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15
Q

amines to amines acting as a base

A

r - water
c - room temp
p - R-NH3+ OH-

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16
Q

ligand exchange of amines

A

r - [Cu(H2O)6]2+ (aq)
c - room temp
p - copper complex ion
[Cu-R-H20]2+

17
Q

secondary, tertiary amine formation from primary amine

A

r - excess CH3CH2Cl in ethanol
c - reflux
p - amine

18
Q

nucleophilic substitution of halogenoalkanes (Sn) to form nitriles

A

r - KCN, ethanol
c - reflux
p - nitrile

19
Q

hydrolysis of nitriles

A

r - HCl (aq)
c - reflux
p - amides

20
Q

how are hydroxynitriles formed from carbonyls?

A

r - KCN, H2SO4
c - reflux, pH 8 buffer
p - hydroxynitrile

21
Q

hydrolysis of dipeptides

A

r - conc. HCl (aq) , H2O
c - reflux
p - amino acid

22
Q

describe amphoteric behaviour

A

when something acts as both an acid and a base

23
Q

how are polyamides formed?

A

from the reaction between dicarboxylic acids and diamines
elimination of water results in long chain polymers
monomer units are linked with amide bonds

24
Q

what else can be used to make polyamides?

A

diacylchlorides

HCl is lost instead of water so should be done in fume cupboard

25
define the term base
proton acceptor / lone pair donator
26
what makes an organic compound more basic?
more alkyl groups inductively donating and stabilising the resulting ion
27
why is ethanamide a weak base compared to an aliphatic primary amine?
delocalised lone pair creates resonance structure with C=O so it becomes less available for bonding
28
what colour do amino acids turn in ninhydrin?
purple/pink/red
29
explain why excess ammonia is needed in organic synthesis
product acts as nucleophile further substitution occurs excess NH3 reduces chance of further subsititution
30
state the feature of an amine that allows it to act as a Bronsted-Lowry base
lone pair of e- on N
31
why are aliphatic amines stronger bases?
alkyl groups that can push e- (inductive effect) | makes lone pairs more available
32
why is ammonia a stronger base than phenylamine?
lone pair on N delocalises | less available for bonding
33
what is meant by the term zwitterion
neutral molecule has +NH3 and COO- groups formed through proton transfer