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Carboxylic Acids
Naming and properties of Carboxylic Acids
17
Organic Chemistry
Undergraduate 2
02/28/2015

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Term
IUPAC naming for carboxylic acids
Definition

Take the longest carbon chain with the carboxyl group

Replace the e with -oic acid.

Term
Benzene's name as a carboxylic acid?
Definition
Benzoic acid
Term
Methane's name as a carboxylic acid?
Definition
Formic Acid
Term
Ethane's name as a carboxylic acid?
Definition
Acetic acid
Term
Butanes name as an acetic acid?
Definition
Butyric Acid
Term
Propane's name as a carboxylic acid?
Definition
Propionoic acid
Term
Common numbering for the carbons following the carbon one in a carboxylic acid chain?
Definition

Greek lettering. 

Carbon 2 =α 

Carbon 3 = β

Carbon 4 = γ

(Alpha, Beta, Gamma)

Term
Benzoic Acid includes what naming system when it has another substituent group attached?
Definition

o, m, p

Ortho, meta, para

Term
How are carboxylic acids prepared?
Definition

2 stage oxidation of a primary alcohol

First stage oxidizes an alcohol to an aldehyde

Second stage oxidizes the aldehyde to an acid

                                   O 

                                  ||

CH3-CH2-OH [O] -> CH3-C-H

 

           O                     O          

    ||                    ||  

CH3-C-H [O]-> CH3-C-OH

 

Term
Carboxylic Acids are more or less polar than most groups?
Definition
Far more polar due to the hydroxyl and carbonyl both being polar groups.
Term
What are the boiling points of carboxylic acids compared to alcohols, ketones and aldeydes of similar mass?
Definition
Greater due to the extra hydrogen bonding
Term
What is the solubility of carboxylic adics in water?
Definition

1-4 carbons are highly soluble

5-7 and benzoic are slightly soluble.

Term
How are carboxylic acids neutralized?
Definition
The addition of a strong base (NaOH and KOH)
Term
What is the result of neutralization of a carboxylic acid?
Definition

Carboxylic acid salt

Carboxlate ion and a metal ion from the base

Term
What is the naming convention for a carboxylic acid salt?
Definition

Primary word becomes the metal ion, replace the -ic acid with -ate 

 O                           O                 

    ||                           ||                    

H-C-OH + NaOH ->H-C-O-Na++H2)

 Formic Acid -> Sodium Formate

Term
What are the carboxylic acid physical properties?
Definition

Solids at room temperature

High melting points

Soluble in water

Term
Describe ionization of carboxylic acids in water.
Definition

The carboxylic acid donates a hydrogen  to the water, making a carboxylate ion and a hydronium ion.

 

   O                             O            

  ||                            ||          

CH3-C-OH + H2O -> CH3-C-O- + H3O

Acetic acid + water -> Acetate ion + hydronium ion

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