Chapter 22-Amines

Question 1

What are Amines derived from?

Answer 1

Ammonia (NH3)

Question 2

Draw out the following:
-Primary Amines
-Secondary Amines
-Tertiary Amines

Answer 2

Question 3

What is the name of naturally occuring amines?

Answer 3

Alkaloids

Question 4

What is the geometry of an amine?

Answer 4

Triginal Planar

Question 5

How many carbons can an amine be soluble in water?

Answer 5

Less than five carbons.

Question 6

Which type of amines have high boiling points and why?

Answer 6

Primary and secondary amines will always have higher boiling points because they can intermoleculary H-bond.

Question 7

Suffix for Amine (Nomenclature)

Answer 7

“-amine”

Question 8

Prefix for Amine (Nomenclature)

Answer 8

“amino-“

Question 9

What is aminobenzene also known as?

Answer 9

Aniline

Question 10

Can amines have chirality?

Answer 10

No! Amines are not optically active.

Question 11

pKb of Ammonia

Answer 11

4.74

Question 12

pKa of Ammonium Ion

Answer 12

9.26

Question 13

True or False: Aryl Amines are less basic than Alkyl Amines.

Answer 13

True, essentially the lone pair on the amine is now delocalized due to the aromatic ring and its pi energy, therefore it is less available to act as a base.

Question 14

How can an Amine be protonated?

Answer 14

By either a weak or strong acid.

Question 15

Does the presence of an Electron Withdrawing Group (EWG) or the presence of an Electron Donating Group (EDG) increase basicity?

Answer 15

The presence of an EDG will increase the basicity/

Question 16

Are amines better nucleophiles or better electrophiles?

Answer 16

Amines are good nucleophiles. (Think: strong base=good nucleophile)

Question 17

What happens when an amine goes under akylation?

Answer 17

The amine will NOT stop reacting, therefore causing it to become a quantenary ammonium salt, making it better nucleophile the more it becomes alylated.

Question 18

What is a Hoffman Elimination? Show by doing the mechanism for the following reaction.

Answer 18

Question 19

What is an imine? (Hint: Draw it out)

Answer 19

Question 20

What reactants/reagents are used in Hoffman Elimination?

Answer 20

-Methyl Iodine (CH3I)
-Ag2O, H2O, and Heat.
-Amine

Question 21

What is following reaction known as?

Answer 21

Reductive Animation

Question 22

What forms in reductive animation?

Answer 22

An imine!

Question 23

What can you reduce an imine with?

Answer 23

1) LAH, H2O
2) NaBH4, ROH
3) NaBH(OAc)3, ROH
4) NaCNBH3, ROH

Question 24

Provide a mechanism using Acylation Reduction for the following reaction:

Answer 24

Question 25

Which type of amines can nitriles form from?
a) primary amines
b) secondary amines
c) tertiary amines

Answer 25

a) primary amines

Question 26

What are the two reagents used in Nitrile reduction?

Answer 26

1) LAH
2) H2O

Question 27

Provide the mechanism to make a nitrosamine.

Answer 27

Question 28

Provide the reaction of how to make a diazonium salt.

Answer 28

Question 29

Which is more stable? Alkyl diazonium or aryl diazonium?

Answer 29

Aryl diazoniums are more stable.

Question 30

What reagent would be used in the sandmeyer reaction? What does it do?

Answer 30

A copper salt would be used. It can be used to install a halogen, cyano, or hyrdoxy group to a ring.

Question 31

What is the mechanism of the nitrosonium ion?

Answer 31