Amines

Question 1

Amines can be thought to be derivatives of….

Answer 1

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

Question 2

What are the four types of Amines? 

Answer 2

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

Question 3

The N in amines is _____ hybridized. 

Answer 3

sp3

Question 4

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

Answer 4

Pyramidal inversion (think of an umbrella) 

Question 5

Tetrahedral ammonium salts with four different are groups are _______. 

Answer 5

Chiral. Chirality cannot be ignored! 

Question 6

Primary amines are named as…..

Answer 6

Alkanamine

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

Question 7

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

Answer 7

Amino

Question 8

Common name of primary amines?

Answer 8

Alkylamines

Question 9

Common name for naming Symmetricalsecondary and tertiary amines?

Answer 9

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

Question 10

How are unsymmetrical secondary and tertiary amines named? 

Answer 10

N- common names of Primary amines.

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

Question 11

How are aromatic amines named? 

Answer 11

As derivatives of aniline

Exceptions see page 470

Question 12

amines have a higher priority than

Answer 12

Alkenes, Alkynes, ethers, and halides

Question 13

What kind of amines can hydrogen bond? 

Answer 13

Primary and secondary

Question 14

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

Answer 14

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

Question 15

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

Answer 15

Tertiary

Question 16

Low molecular weight amines have _______ odors

Answer 16

Fishlike

Question 17

Diamines smell like…

Answer 17

Cadavers

Question 18

Amines with odd number of nitrogens have ____ molecular weights.

Answer 18

Odd

Question 19

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

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

Answer 19

Primary amines have two
Secondary amines have one
Tertiary have none

Question 20

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

Answer 20

2.2-3.0 ppm

Does not split signals of adjacent hydrogen

Question 21

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

Answer 21

30-50

Question 22

Complex basic amines derived from plants

Answer 22

Alkaloids

Question 23

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

Answer 23

2-Phenylethylamine and derivatives

Question 24

What are the three ways to prepare amines?

Answer 24

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

Question 25

For nucleophilic substitution to get primary amines use…

Answer 25

2ŃH3 and R-X

Question 26

For secondary and tertiary amines, use… | And quaternary?

Answer 26

R’NH2 (secondary) R’2NH (Tertiary)  Access alkyl halide and R’3Ń (amine with three groups) 

Question 27

What is used in the Gabriel synthesis of primary amines? 

Answer 27

-Alkyl halide + phthalimide OH- ———-> H20 -Primary Amine + dicarboxylate and X-

Question 28

What is used for the reduction of nitro compounds? What kind of amine is produced? 

Answer 28

H2/Pd Fe/HCL Sn/HCL Primary amine R-ŃH2

Question 29

What is used to reduce nitriles? 

Answer 29

1. LiAlH4 2. H2O Produces a primary amine

Question 30

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

Answer 30

NaBH3CN

Question 31

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

Answer 31

Bases, Nucleophiles

Question 32

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

Answer 32

Less

Question 33

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

Answer 33

Stronger

Question 34

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

Answer 34

Basic

Question 35

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

Answer 35

Basic

Question 36

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

Answer 36

Basic

Question 37

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

Answer 37

Less See page 489

Question 38

Alkylamines are ________ than amides

Answer 38

More basic See page 489

Question 39

Arylamines are _____ than NH3

Answer 39

Less basic

Question 40

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

Answer 40

Less basic Localized electron pairs are more basic Pg. 490

Question 41

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

Answer 41

Lower

Question 42

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

Answer 42

Substitution, addition

Question 43

Reaction converts first an amine to a quaternary Ammonium salt, the salt is in converted to an alkene What kind of reaction is this?

Answer 43

Hoffman elimination reaction

Question 44

What is the major product in Hoffman elimination reaction?

Answer 44

Non-Zaisev (Least substituted) 

Question 45

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

Answer 45

Crystalline phenylhydrazones (imines) with distinctive MP

Question 46

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

Answer 46

Semicarbazide

Question 47

What can be used to identify aldehydes and ketones? 

Answer 47

Semicarbazone (primary Amine) 

Question 48

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

Answer 48

Haworth projections