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Naming and properties of Amines
Naming conentions and properties
25
Organic Chemistry
Undergraduate 2
03/07/2015

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Cards

Term
What are the three classifications of amines?  (Think alcohols)
Definition

Primary, Secondary and Tertiary

 

Term
What is a primary amine?
Definition

One nitrogen bonded to one carbon atom

CH3-NH2

Term
What is a secondary amine?
Definition

A nitrogen atom bonded to two carbon atoms.

CH3-NH-CH3

Term
What is a tertiary amine?
Definition

A nitrogen atom bonded to three carbon atoms.

CH3-N-CH3

        |

        CH3

Term
What is the name of an amine with no carbon attachments? (NH3)
Definition
Ammonia
Term
What is the physical atom arrangement of ammonia and amines?
Definition
Trigonal pyramidal.
Term
What is the IUPAC naming for amines?
Definition

The e from the alkane parent name of the carbon chain is replaced with -amine

CH4 -> CH3-NH2

Methane->Methanamine

Term
What is the naming convention for secondary and tertiary amines?
Definition

Use the prefix N- to name alkyl groups attached to the N atom, listed alphabetically.

 

CH3-CH2-N-CH3

               |

               CH3

N,N Dimethylethanamine

Term
How do you name an amine with 2 nitrogen functional groups
Definition

Diamine

 

H2N-CH3-CH3-CH3-CH3-NH2

1,4 Butanediamine

Term
Is an amine a higher priority than Alcohol or hydroxyl?
Definition
No, it will be a lower priority naming and a substituent group.
Term
How do you name a molecule where there is an NH2 that is not the higher priority functional group?
Definition

The substituent group is named as amno to mark it's location.

 

CH3-CH-CH2-OH

        |

        NH2

2-Amino-1-propanol

Term
What is the name of an amine group on a benzene?
Definition

Aniline

 

BR-[Benzen ring]-NH2

4-Bromoaniline

p-bromoaniline

Term
Where do amines fall on the boiling point scale?
Definition

Higher than alkanes, lower than alcohols

Polar N-H bond allows hydroge bonding, but nitrogen is less electronegative than Oxygen.

Term
How soluble are amines in water?
Definition
Smaller amines are due to hydrogen bonding, however more than 6 is a much lower chance.
Term
What do you create when you add ammonia to water? (Ionization of NH3 + H2O)
Definition

Ammonium ion and a hydroxide ion

NH4+ + OH-

Term
What do you get when an amine + water?
Definition

Ammonium Ion

(Aklyl ammonium ion and a hydroxide ion)

Term
How do you name the result of an anime  that accepts an ion from water?
Definition

The suffix -amine is replaced with -ammonium ion

 

CH3-NH2 + H2O -> CH3-NH3+ + OH-

Methylamine -> Methylammonium ion 

Term
How do you name a secondary amine that accepts a proton from water?
Definition

Dimethylammonium ion

 

CH3-NH-CH3 + H2O -> CH3-N+H2-CH3 + OH-

Term
Describe basicity of amines.
Definition
K values for amines are less than 10-3 at 25 celcius.  Equilibrium favores amine molecules.  Solutions of amines have basic pH values and turn a red litmus paper blue.
Term
What is the product of a neutralization reaction of amines?
Definition
Amine salt
Term
What is the reaction to form an amine salt?
Definition

The lone pair of electrons on the nitrogen accepts a proton from an acid to make an amine salt.  (No water is formed.)

CH3-NH2 + HCL -> CH3-NH3+-CL-

Methylamine -> Methylammonium chloride

Term
What do you call a nitrogen atom attached to 4 carbon groups?
Definition

Quaternary ammonium ion

The nitrogen has a positive charge and is an amine salt.)

  CH3  

   |       

CH2-N-CH3CL-

|    

        CH3       

Tetramethylammonium Chloride

Term
How do you name an amine salt?
Definition
Replace the -amine part of the name with -ammonium followed by the name of the negative ion.
Term
What are the ionic properties of amine salts?
Definition
Amine salts are ionic with strong attractions between positively charged ammonium ion and an anion, usually chloride)
Term
What happens when an amine salt reacts with a strong base? (NaOH)
Definition

It is converted back to the amine, now called a free amine or free base.

CH3-NH3+CL- + NaOH - CH3-NH2 + NaCl + H2O

Methylammonium chloride -> Methylamine

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