CHEM 1406 Concept Review: Carboxylic Acids, Esters, Amines, & Amides

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Name of
Functional Group		 Carboxylic Acid Ester Amine Amide
Special Characteristic A carbon at the end of a chain is double bonded to one oxygen and single bonded to an “-OH” A carbon at the end of a chain is double bonded to one oxygen and single bonded to another oxygen connected to a carbon chain on the other side Nitrogen is attached to one or more carbons or carbon chains A carbon at the end of a chain is double bonded to one oxygen and single bonded to a nitrogen, which may or may not be attached to other carbons.
Example 1406 Ch 14 img 1.png 1406 Ch 14 img 2.png 1406 Ch 14 img 3.png 1406 Ch 14 img 4.png

 

 

Naming Carboxylic Acids and Esters

Carboxylic Acids Esters
Step 1

Find the longest continuous chain of carbon atoms that has a carboxylic acid group (-COOH) at the end, and use the name for a chain with that number of carbons but change the ending to “-oic acid”. 

Example:  1406 Ch 14 img 5.png

The longest carbon chain is 3, so this would be called “propanoic acid”.

Find the oxygen that is in the middle of the carbon chain and isolate the two groups on either side.

 

Example:  1406 Ch 14 img 6.png

 

 
Step 2

Number the carbon atoms in the longest chain, beginning with the carbon that is part of the carboxylic acid group (-COOH).  Then, name each substituent and assign a number indicating its location on the main chain. 

Example:  1406 Ch 14 img 7.png

The methyl group is on carbon number 2, so this is called “2-methyl propanoic acid”.

The more important side will be the one with the carbonyl group (C==O).  Name that group according to the number of carbons it has and give it an “-oate” ending.  The less important group on the other side is named like a substituent.  The more important group is listed last in the name.

Example:  1406 Ch 14 img 8.png

The name of this compound is
"ethyl propanoate".


 

Naming Amines and Amides

Amines (Common Naming) Amines (IUPAC Naming) Amides
Step 1

Identify the groups on either side of the nitrogen, and name them like substituents.

 

Example:  1406 Ch 14 img 9.png

Look for the longest carbon chain that is attached to the nitrogen and number the carbons starting on the side closest to that nitrogen.

NOTE:  You must indicate the number of the carbon on the longest chain that is attached to the nitrogen.

Example:  

1406 Ch 14 img 10.png

Starting with the name for a 3-carbon chain, add the ending “–amine”. The root name for this compound is therefore

“1-propanamine”.

Look for the longest carbon chain that is attached to the amide group and number the carbons starting with the carbon with the carbonyl (C=O)

Example:
1406 Ch 14 img 11.png

 

Starting with the name for a 4-carbon chain, add the ending “–amide”. The root name for this compound is therefore “butanamide”.
Step 2

Name the two groups in alphabetical order followed by the word “amine”.  There should be NO spaces between either of the groups or the word “amine”.

Example:

ethylmethylamine

Identify and name the smaller groups as substituents.  For the substituent attached to the nitrogen, instead of giving it a number, label it with an “N-“.

Example:

1406 Ch 14 img 12.png

Identify and name the smaller groups as substituents.  For the substituent attached to the nitrogen, instead of giving it a number, label it with an “N-“.

Example:
1406 Ch 14 img 13.png
Step 3 N/A

Write the names of the substituents along with their numbers in alphabetical order followed by the root name of the compound with no spaces in between.

Example:

N-ethyl-2-methyl-1-propanamine

Write the names of the substituents along with their numbers in alphabetical order followed by the root name of the compound with no spaces in between.

Example:

N-methylbutanamide