AC13: Organic N Compounds Flashcards

1
Q

What is an amine

A

A compound with NH or NH2 or N as its functional group

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2
Q

What are the differences between a primary, secondary, and tertiary amine

A

primary amine has NH2 - N is bonded to one alkyl chain
secondary amine has NH - N is bonded to two alkyl chains
tertiary amine has N - N is bonded to three alkyl chains

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3
Q

What does ethanolic mean

A

dissolved in ethanol

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4
Q

How do you prepare aliphatic primary amines

A

Haloalkane (chloroalkane) + ammonia and (heat with excess ethanolic ammonia) -> primary amine + hydrogen halide (HCl)

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5
Q

What is the mechanism for preparing amines and explain it

A

Nucleophilic substitution
curly arrow from lone pair on N to the delta positive on the haloalkane. Curly arrow from delta positive carbon to halogen. Forms amine with positive charge on N and a chloride ion. Add OH- to deprotonate the organic product to form the free amine

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6
Q

How do you prepare aliphatic secondary and tertiary amines

A

Add excess primary amine in ethanolic solution to a chloroalkane and heat to give a desirable yield of secondary amine. Tertiary amines are formed from further substitution of secondary amines therefore use secondary amines.

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7
Q

How do you prepare aromatic amines

A

benzene + nitric acid (50 degrees celsius, conc HNO3, conc H2SO4) -> nitrobenzene + water
nitrobenzene + 6 [H] ( Sn/conc HCl, heat under reflux) -> aromatic amine + 2 H2O

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8
Q

How do you prepare amines fro nitriles and how is this useful

A

nitrile + 2H2 (Ni/Pt catalyst and heat) -> amine
useful reaction to extend the carbon chain

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9
Q

What makes an amino acid, an alpha amino acid

A

The two functional groups are bonded to the “alpha carbon” (2nd carbon)

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10
Q

What is an amide

A

A compound with a N-C=O functional group

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11
Q

What are the differences between a primary, secondary, and tertiary amide

A

primary amide has NH2 - N is bonded to one alkyl chain
secondary amide has NH - N is bonded to two alkyl chains
tertiary amide has N - N is bonded to three alkyl chains

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12
Q

How do you prepare primary amides

A

Acyl chloride + ammonia (excess ethanolic ammonia) -> amide + ammonium chloride

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13
Q

How do you prepare secondary amides

A

Acyl chloride + primary amine (excess ethanolic primary amine) -> amide + NH3Cl (bonded to alkyl group from primary amine)

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14
Q

How do you prepare tertiary amides

A

Acyl chloride + secondary amine (excess ethanolic secondary amine) -> amide + NH2Cl (bonded to the two alkyl groups from secondary amine)

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15
Q

What is a nitrile

A

a compound with a CN functional group (C triple bond N)

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16
Q

State 2 ways to prepare nitriles

A

from carbonyls or from haloalkanes

17
Q

How do you prepare nitriles from carbonyls

A

aldehyde/ketone + HCN (NaCN + conc sulfuric acid) -> nitrile (the double bonded O is now -OH)

18
Q

Explain the mechanism nitriles are prepared from carbonyls

A

Nucleophilic addition
curly arrow from :CN- ion to partial positive charge on central C
curly arrow from double bond (C=O) to O
curly arrow from :O- to H+
forms nitrile with hydroxyl group

19
Q

How do you prepare nitriles from haloalkanes

A

haloalkane + CN- (NaCN + ethanolic solution) -> nitrile + halide ion

20
Q

Explain the mechanism nitriles are prepared from haloalkanes

A

Nucleophilic substitution
curly arrow from :CN- ion to partial positive charge on C bonded to halogen
curly arrow from bond (C-halogen) to halogen
forms nitrile and halide ion

21
Q

How can you reduce nitriles and what is produced

A

nitrile + 2H2 (Ni/Pt catalyst and heat) -> amine

22
Q

How can you hydrolyse nitriles and what is produced

A

nitrile + 2H2O + HCl (heat and aqueous HCl) -> Carboxylic acid + ammonium chloride