Lecture 25
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Lecture 25. Amine nomenclature Basicity of amines Synthesis of amines (on board). Nomenclature of Aldehydes & Ketones: IUPAC Rules. Functional GroupSuffix if highest priority groupAs a substituent CO 2 H carboxylic acid-oic acid-carboxy-

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Lecture 25

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Lecture 25

Lecture 25

  • Amine nomenclature

  • Basicity of amines

  • Synthesis of amines (on board)


Lecture 25

Nomenclature of Aldehydes & Ketones:

IUPAC Rules

Functional GroupSuffix if highest priority groupAs a substituent

CO2H carboxylic acid-oic acid-carboxy-

CO2R ester-oate-alkoxycarbonyl-

CO2NR2amide-amide-carbamoyl-

CHO aldehyde-al-oxo-

CRO ketone-one-oxo-

OH alcohol-ol-hydroxy-

NR2 amine-amine-amino-

SH thiol-thiol-mercapto-


Lecture 25

Nomenclature of Primary Amines: IUPAC

Primary Amines

1. Find the longest chain to contain the -NH2 group; this is the parent chain.

2. This parent chain’s name ends in ‘amine’ - the suffix. E.g., take

alkane and convert to alkanamine.

3. Number the parent chain such that the carbon bearing the -NH2 has the

lowest number possible. Give location of -NH2 group in name.

4. Give name; be sure to list substituents alphabetically and to give their

location; these are the prefixes. Remember that sec-, tert-, o-, m-, p-,

di-, tri-, tetra- are not considered when alphabetizing, but iso is.

Name the following:


Lecture 25

Nomenclature of Primary Amines: Common Name

Primary Amines

If the primary amine is a simple structure, that is the carbon group is simple,

then the common name is easy to determine. In the common name, the amine’s

name is “alkyl amine”; two words.

Name the following:


Lecture 25

Nomenclature of 2° & 3° Amines: IUPAC

B. 2° & 3° Amines

1. Find the longest R group chain to contain the -NR2/-NHR group; this is the parent

chain. The carbon of the parent chain that’s bound to the N gets the #1

designation.

2. This parent chain’s name ends in ‘amine’ - the suffix. E.g., take

alkane and convert to alkanamine.

3. The other R groups are listed first (as the first word) and alphabetically with

an “N-” in front of them to designate that the R group is bound to the nitrogen.

(Similar to 2° and 3° amide nomenclature.)

4. Give name; be sure to list the parent chain substituents alphabetically and to

give their location; these are the prefixes. Remember that sec-, tert-, o-, m-, p-,

di-, tri-, tetra- are not considered when alphabetizing, but iso is.

Name the following:


Lecture 25

Nomenclature of 2° & 3° Amines: Common Name

B. 2° & 3° Amines

1. Identify the R groups bound to nitrogen.

2. List the alkyl groups alphabetically. Remember not to alphabetize di-, tri-, sec-, or

-tert.

3. End the name with the word “amine”.

Name the following:


Lecture 25

Nomenclature: Heterocyclic Amines

Parent names of some heterocyclic amines:

Name the following:


Lecture 25

Basicity of Amines

  • Basicity of amines dominates its chemistry.

  • Measure of basicity is pKb:


Lecture 25

Basicity of Amines

  • The lower the pKb value, the more basic the amine.

  • pKb values are related to the pKa values of the conjugate acids:

  • pKa + pKb = 14

  • Example: NH3 has a pKb = 4.74, so the pKa of its conjugate

  • acid, NH4+ is 9.26.

  • It is common to find the pKa for the ammonium salt; then need

  • to convert to pKb.

  • Unlike carboxylic acids, the effect of the R substituents on the

  • nitrogen’s basicity is minimal except for aniline derivatives.


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