Lecture 10

Question 1

What is an Amine?

Answer 1

When 1 or more HYDROGENS atoms on AMMONIA are replaced with R group.

Question 2

What is Amide?

Answer 2

Derivatives of CARBOXYLIC ACIDS.

Question 3

In an amine, the nitrogen atom has a lone pair of electrons which makes amines what?

Answer 3

1. Nucleophilic

2. Basic

Question 4

In an aliphatic amine what bonding is shown in the nitrogen? What does this mean?

Answer 4

sp3 hybridized so no DOUBLE BONDS.

Question 5

C-N-C bond angel?

Answer 5

107o.

Question 6

In an aromatic amine what bonding is shown in the nitrogen? Where is the lone pair?

Answer 6

Nitrogen is sp2 hybridized. Lone pair which occupies the p- orbital is DELOCALISED.

Question 7

Why is the reactivity between aromatic and aliphatic amines different?

Answer 7

Lone pair undergoes SUBSTIUTION with the pie system (Aromatic Amine)

Question 8

What are the classifications of amines?

Answer 8

PRIMARY AMINE- ONE alkyl/ aryl group.
SECONDARY AMINE- TWO alkyl/ aryl groups.
TERTIARY AMINE- THREE alkyl/ aryl groups.

Question 9

Naming Amines- IUPAC 1

Answer 9

P: Remove the ‘e; from alkane name and add ‘amine’.
Eg: Propan-1-amine.
S/T: Name longest chain + shorter chains are named n- alkyl.
Eg: N- ethyl- N- methyl- propylamine.

Question 10

Naming Amines- IUPAC 2

Answer 10

P: Amino group is a substitute on longest carbon chain.
Eg: 1- aminopropane.
S/T: Shorter substitutes go in front of ‘amino’.
Eg: N-ethyl-N-methyl- aminopropoane.

Question 11

Naming Amines- Common Naming.

Answer 11

P: Names as alkylamines. 
Eg: n- propylamine 
(n- unbranched).
S/T: N alkyl groups or simple listed. 
Eg: N-ethly-N-methyl- propylamine.

Question 12

Describe the solubility of low molecular weight amines.

Answer 12

Soluble in water.

Soluble in Organic Solvents.

Question 13

Describe the boiling point of amines.

Answer 13

High boiling points compared to alkanes.

P and S amines have lower boiling points in comparison with alcohols.

Question 14

Why have alcohols got higher boiling points than amines?

Answer 14

NITROGEN is LESS ELECTRONEGATIVE than OXYGEN.

Question 15

How many hydrogen bonds can primary, secondary and tertiary amines form?

Answer 15

P- 3
S-2
T- 0

Question 16

Tertiary amines usually make 0 hydrogen bonds what is the exception, why?

Answer 16

When a bond formed with WATER as it has a SMALL steric hinderance.

Question 17

When amines react with acids or water what is produced?

Answer 17

Alkylammonium Salt

Question 18

How are Alkylammonium Salts named?

Answer 18

CHANGING “AMINE” to “AMMONIA

Question 19

What type of reaction occurs during the reduction of nitro compounds?

Answer 19

Electrophilic Substitution

Question 20

What classification of amine is the product of the reduction of nitro compounds?

Answer 20

Primary Amine

Question 21

What reagents and conditions are needed for the reduction of nitro compounds?

Answer 21

Hydrogen and TM Catalyst

Question 22

In the reduction of nitro compounds what is the NO2 group bonded to?

Answer 22

Aromatic Group.

Question 23

What classification of amine is the product of the reduction of nitriles?

Answer 23

Primary

Question 24

What reagents and conditions are needed for the reduction of nitriles?

Answer 24

Hydrogen and Ni Catalyst

Question 25

What classification of amine is the product of the reduction of amides?

Answer 25

Primary, Secondary and Tertiary.

Question 26

What reagent is needed for the reduction of amides?

Answer 26

LiAlH4

Question 27

What are the products from the Hofmann Degradation of Amines?

Answer 27

Primary Amines

Question 28

What reagent is used for Hofmann Degradation of amines?

Answer 28

KOBr

Question 29

What is the reactant needed to be transferred with KOBr to form an amine?

Answer 29

Amides deprived from AMMONIA not from nitrogen atoms bonded to CARBON

Question 30

In industry what what is the reactant which produces an alkylamines? Via what reaction?

Answer 30

Alcohols | Nucleophilic Substitution

Question 31

What classification of amine is produced from an alcohol?

Answer 31

Primary Amine

Question 32

To produce an amine, what is the additional reactant needed with an alcohol? What are the conditions for this reaction?

Answer 32

Ammonia | High temperature and pressure.

Question 33

In the lab, amines can be produced from alkyl halides, what classification of amines is produced?

Answer 33

PRIMARY SECONDARY TERTIARY QUATERNARY AMMONIUM IONS.

Question 34

What does reaction of amines depend on?

Answer 34

1. Lone Pair to act as a base. | 2. Nitrogen to act as a nucleophile.

Question 35

What classification of amines can be produced from carbonyls?

Answer 35

Primary Secondary Tertiary

Question 36

Reagent in the reaction which changes a carbonyl to an imine?

Answer 36

Ammonia

Question 37

How is a carbonyl changed to an amine?

Answer 37

1. Carbonyl to an Imine (NH3) | 2. Add H2 & TM Catalyst, NaBH3CN or NaBH(OAc)3 in acidic conditions to reduce the imine to amine.

Question 38

What is an imine? What is an imine termed in biology?

Answer 38

Functional group is a DOUBLE BOND between a Carbon and Nitrogen atoms. SCHIFF BASE.

Question 39

In the body how is ammonia used to synthesise amino acids?

Answer 39

1. NH4+ to Imine which is REDUCED via the biological reducing agent NADPH to glutamate. 2. Glutamate can be then converted into another amino acid via a condensation reaction using TRANSFERASE enzyme, glutamine synthase.

Question 40

What does PYRIDOXAL PHOSPHATE do?

Answer 40

Transfer N groups with an aldehyde.

Question 41

What is Alkylation?

Answer 41

Transfer of alkyl group from one molecule to another.

Question 42

What type of reaction is alkylation?

Answer 42

Nucleophilic Substitution

Question 43

In acylation what is a reactant is this reaction?

Answer 43

Carboxylic Derivatives.

Question 44

What are the reagents (biological and lab) found in acylation reactions?

Answer 44

Lab: Acid Chlorine Bio: Cofactor CoA.

Question 45

What is reacted with R-Ammonia to form N2-R?

Answer 45

NaNO2 +2HX forms HONO (Nitrous Acid)

Question 46

What is the Diazonium salt formation?

Answer 46

AMINE functional group is turned into ANOTHER functional group.

Question 47

In the diazonium salt formation what is formed when R+ reacts with: X- (Main nucleophile from the acid. Water Aliphatic Amine

Answer 47

Alkyl Halide Alcohol (N2 is replaced with OH- Phenol). Alkene

Question 48

Which diazonium salts (Aliphatic/ Aromatic) is more useful in creating a diazonium salt? Why?

Answer 48

Aromatic because alkyl diazonium salt is too reactive.

Question 49

What does Hofmann Elimination produce?

Answer 49

Tertiary Amine

Question 50

Hofmann Elimination- What are the requirements for a quaternary ammonium salt to be converted into an alkene and tertiary amine?

Answer 50

Base and Heat.