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Ochem 2 > Amines > Flashcards

Amines Flashcards

1
Q

Amines can be thought to be derivatives of….

A

Ammonia (Instead of three hydrogen it’s three R groups)

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2
Q

What are the four types of Amines? 

A
  • primary (One R group)
  • secondary
  • Tertiary
  • Quaternary (ammonium salts, 4 R groups) 
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3
Q

The N in amines is _____ hybridized. 

A

sp3

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4
Q

Simple amines are CHIRAL But chirality can be ignored as the two enantiomers inner convert rapidly at room temperature through a ____________. 

A

Pyramidal inversion (think of an umbrella) 

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5
Q

Tetrahedral ammonium salts with four different are groups are _______. 

A

Chiral. Chirality cannot be ignored! 

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6
Q

Primary amines are named as…..

A

Alkanamine

The parent chain is the longest carbon chain that contains the amine group 

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7
Q

What is the -NH2 group called when naming primary amines with more than one functional group?

A

Amino

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8
Q

Common name of primary amines?

A

Alkylamines

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9
Q

Common name for naming Symmetricalsecondary and tertiary amines?

A

Prefixes such as di, tri, tetra,… are used. 

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10
Q

How are unsymmetrical secondary and tertiary amines named? 

A

N- common names of Primary amines.

N-methylethylamine (common name)
N-methylethanamine (IUPAC name) 

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11
Q

How are aromatic amines named? 

A

As derivatives of aniline

Exceptions see page 470

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12
Q

amines have a higher priority than

A

Alkenes, Alkynes, ethers, and halides

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13
Q

What kind of amines can hydrogen bond? 

A

Primary and secondary

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14
Q

 because primary and secondary amines can H bond, they have….

A

Higher melting point and boiling point than comparable substances but lower than alcohols and carboxylic acids

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15
Q

___________ amines have lower boiling point and nothing point and then primary amines. 

A

Tertiary

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16
Q

Low molecular weight amines have _______ odors

A

Fishlike

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17
Q

Diamines smell like…

A

Cadavers

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18
Q

Amines with odd number of nitrogens have ____ molecular weights.

A

Odd

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19
Q

Amines have N-H bands at 3300-3500cm-1

How many of these bands do primary, secondary, tertiary amines have? 

A

Primary amines have two
Secondary amines have one
Tertiary have none

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20
Q

The N-H proton is desheilded at ____ -_____ ppm.

A

2.2-3.0 ppm

Does not split signals of adjacent hydrogen

21
Q

The C of C-N is desheilded at ____-____pppm

A

30-50

22
Q

Complex basic amines derived from plants

A

Alkaloids

23
Q

These interfere with the normal functioning of the brain. Some are pain killers.

A

2-Phenylethylamine and derivatives

24
Q

What are the three ways to prepare amines?

A
  • nucleophilic (SN2) Substitution with nitrogen Nucleophiles
  • Reduction of nitrogen containing functional groups
  • Reductive amination of Aldehydes and ketones
25
Q

For nucleophilic substitution to get primary amines use…

A

2ŃH3 and R-X

26
Q

For secondary and tertiary amines, use…

And quaternary?

A

R’NH2 (secondary)
R’2NH (Tertiary) 

Access alkyl halide and R’3Ń (amine with three groups) 

27
Q

What is used in the Gabriel synthesis of primary amines? 

A

-Alkyl halide + phthalimide

OH-
———->
H20

-Primary Amine + dicarboxylate and X-

28
Q

What is used for the reduction of nitro compounds?

What kind of amine is produced? 

A

H2/Pd
Fe/HCL
Sn/HCL

Primary amine R-ŃH2

29
Q

What is used to reduce nitriles? 

A
  1. LiAlH4
  2. H2O

Produces a primary amine

30
Q

What is the catalyst for reductive amination of Aldehydes and ketones? 

A

NaBH3CN

31
Q

Amines Usually lone pair of electrons in nitrogen to react as __________ or _________.

A

Bases, Nucleophiles

32
Q

For a reaction to take place the PKA of the reactants Has to be ________ Than the PKA of the product. 

A

Less

33
Q

Be higher the PKA of the conjugate acid, the __________ the amine as a weak base And vice versa

A

Stronger

34
Q

Alkyl amines are more _____ than NH3 since the alkyl groups are Electron donating groups (EDG) 

A

Basic

35
Q

Alkyl amines are more _______ than aniline because the long pair of electrons on the end is de localize in Aniline through resonance. 

A

Basic

36
Q

EDG (-NH2, -OH, -OR, -NHCOR, -R) make arylamines more ______ than aniline.

A

Basic

37
Q

EWG (-X, -CHO, -COR, -COOR, -COOH, -CN, -SO3, -NO2, NR3+) make arylamines _______ basic than aniline.

A

Less

See page 489

38
Q

Alkylamines are ________ than amides

A

More basic

See page 489

39
Q

Arylamines are _____ than NH3

A

Less basic

40
Q

Electron pairs that are de-localized in part of the aromatic system are more or less basic than lone pairs that are localized? 

A

Less basic

Localized electron pairs are more basic

Pg. 490

41
Q

Does a higher or lower sp3 character make it more basic?

A

Lower

42
Q

Amines react with carbonyl groups to give ___________ or ___________ compounds.

A

Substitution, addition

43
Q

Reaction converts first an amine to a quaternary Ammonium salt, the salt is in converted to an alkene

What kind of reaction is this?

A

Hoffman elimination reaction

44
Q

What is the major product in Hoffman elimination reaction?

A

Non-Zaisev (Least substituted) 

45
Q

Phenyl hydrazine and 2,4-DNP (primary amines) react with aldehydes and ketones to give….

A

Crystalline phenylhydrazones (imines) with distinctive MP

46
Q

____________ (a primary amine) reacts with aldehydes and ketones to give crystalline semicarbazones (imines) 

A

Semicarbazide

47
Q

What can be used to identify aldehydes and ketones? 

A

Semicarbazone (primary Amine) 

48
Q

What type of projections are used to show the sugars in DNA and RNA?

A

Haworth projections

Ochem 2 (10 decks)

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