13: Amines (Part 1)

Question 1

this uses an aldehyde or ketone to replace one H atom on a nitrogen atom by an alkyl group, making a more substituted amine

Answer 1

reductive amination

Question 2

____________ and ___________ amines are also capable of intermolecular hydrogen bonding, because they contain N – H bonds.

Answer 2

Primary, secondary

Question 3

_______________ groups add electron density to the benzene ring, making the arylamine
more basic than aniline

Answer 3

Electron-donor

Question 4

Nucleophilic attack of NH3 on the carbonyl group forms an?

Answer 4

imine

Question 5

All amines having _________ are H2O soluble because they can hydrogen bond with H2O.

Answer 5

≤ 5 C’s

Question 6

these are classified as 1°, 2°, or 3° by the number of alkyl groups bonded to the nitrogen atom

Answer 6

amines

Question 7

Amines are ___________ in organic solvents regardless of size

Answer 7

soluble

Question 8

this replaces a C=O by a C – H and C – N bond

Answer 8

reductive amination

Question 9

Reduction of the imine forms an?

Answer 9

amine

Question 10

The Gabriel synthesis begins with reaction of primary alkyl halide with phthalimide, followed by?

Answer 10

hydrolysis

Question 11

these react as nucleophiles with compounds that contain electrophilic carbons

Answer 11

amines

Question 12

these are more basic than NH3

Answer 12

alkylamines

Question 13

The ______________________ converts an alkyl halide into a 1° amine by a two-step process

Answer 13

Gabriel synthesis

Question 14

these react as bases with a variety of organic and inorganic acids

Answer 14

amines

Question 15

Three types of reactions are used to prepare an amine:

Answer 15

[1] Nucleophilic substitution using nitrogen nucleophiles
[2] Reduction of other nitrogen-containing functional groups
[3] Reductive amination of aldehydes and ketones

Question 16

Electron-withdrawing groups remove electron density from the benzene ring, making the arylamine _________ than aniline

Answer 16

less basic

Question 17

these are stronger bases and nucleophiles than other neutral organic compounds

Answer 17

amines

Question 18

Amines exhibit ______________ interactions because of the polar C – N and N – H bonds.

Answer 18

dipole–dipole

Question 19

Amines having _________ are H2O insoluble because the nonpolar alkyl portion is too large to dissolve in the polar H2O solvent

Answer 19

> 5 C’s

Question 20

Any factor that decreases the electron density (electron withdrawing groups) on N decreases an amine’s?

Answer 20

basicity

Question 21

these are less basic than alkylamines

Answer 21

arylamines

Question 22

The Gabriel synthesis converts an alkyl halide into a 1° amine by a two-step process:

Answer 22

nucleophilic substitution followed by hydrolysis

Question 23

this adds one R group to the nitrogen atom

Answer 23

reductive amination

Question 24

Any factor that decreases the electron density (______________________________) on N decreases an amine’s basicity

Answer 24

electron withdrawing groups

Question 25

these are organic nitrogen compounds

Answer 25

amines

Question 26

In terms of increasing basicity:

Answer 26

amides < arylamines < NH3 < 1o < 2o < 3o

Question 27

this is formed by replacing one or more hydrogen atoms of ammonia (NH3) with alkyl groups

Answer 27

amines

Question 28

Substituted anilines are more or less basic than ___________ depending on the nature of the substituent

Answer 28

aniline

Question 29

these react as bases with compounds that contain acidic protons

Answer 29

amines

Question 30

final product in nucleophilic substitution of amines

Answer 30

quaternary ammonium salt

Question 31

Electron-donor groups add electron density to the benzene ring, making the arylamine
_______________ than aniline.

Answer 31

more basic

Question 32

Any factor that increases the electron density (__________________________) on the N atom increases an amine’s basicity

Answer 32

electron donating groups

Question 33

The Gabriel synthesis begins with reaction of primary alkyl halide with ______________, followed by hydrolysis

Answer 33

phthalimide

Question 34

Amides are much less ______ than amines

Answer 34

basic

Question 35

this begins with reaction of primary alkyl halide with phthalimide, followed by hydrolysis

Answer 35

Gabriel synthesis

Question 36

this exhibit dipole–dipole interactions because of the polar C – N and N – H bonds

Answer 36

Amines

Question 37

The most effective reducing agent for reductive amination of aldehyde and ketone is?

Answer 37

sodium cyanoborohydride (NaBH3CN)

Question 38

With a 1° or 2° amine as starting material, ______________________ is used to prepare 2° and 3° amines, respectively.

Answer 38

reductive amination

Question 39

______________________ groups remove electron density from the benzene ring, making the arylamine less basic than aniline.

Answer 39

Electron-withdrawing

Question 40

this is a two-step method that converts aldehydes and ketones into 1°, 2°, and 3° amines

Answer 40

reductive amination