Carboxylic Acids

By: Courtney and Amelie

www.bhmpics.com www.ansi.okstate.edu www.live-live.com en.wikipedia.org 

General Formula and Structure

• The general formula for a carboxylic acid is: Cn H2n+1 COOH or R C OH the R

variable representing the first part of the name.

EX: Methanoic acid H C OH• The general structure for a carboxylic acid

is:AX₃ Planar

O

O

Naming Scheme

• Naming a Carboxylic acid according to the IUPAC system requires you to drop the e and add oic acid to the end.

Ex: propane → propan → propanoic acid parent chain name , drop the e, add oic acid

www.gcsescience.com 

Naming Scheme• Double and Triple bondsWith double and triple bonds you name them in a very 

similar way to which you would name and alkene or alkyne.

Using the ex from the last slide: with a double bondPropane     Propen    Propenoic acid  2-Propenoic acidBut remember to number where the double or triple bond 

is keeping in mind that the carboxyl group takes priority.

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Naming Scheme

• The last naming scheme to cover is attachments. Using the example from above.

Propane   Propan  Propanoic acid  there is one methyl attachment at 2  so it now becomes 2- methyl Propanoic acid.

www.chemspider.com 

More NamingCarbon Atoms Common Name IUPAC Name Chemical Formula

1 Formic Acid Methanoic Acid HCOOH

2 Acetic Acid Ethanoic Acid CH₃COOH

3 Propionic Acid Propanoic Acid CH₃CH₂COOH

4 Butyric Acid Butanoic Acid CH₃(CH₂) ₂COOH

5 Valeric Acid Pentanioic Acid CH₃(CH₂) ₃COOH

6 Caproic Acid Hexanoic Acid CH₃(CH₂) ₄COOH

7 Enanthic Acid Heptanoic Acid CH₃(CH₂) ₅COOH

8 Caprylic Acid Octanoic Acid CH₃(CH₂) ₆COOH

9 Pelargonic Acid Nonanoic Acid CH₃(CH₂) ₇COOH

10 Capric Acid Decanoic Acid CH₃(CH₂) ₈COOH

Reaction Synthesis• Carboxylic Acids react with bases to form carboxylate

salts, in which the hydrogen of the hydroxyl (-OH) group is replaced with a metal cation.

• In the reaction below Acetic Acid reacts with sodium bicarbonate to form sodium acetate, carbon dioxide, and water.

                        CH₃COOH + NaHCO₃ → CH₃COONa + CO₂ + H₂O

• Also carboxylic acids can react with alcohols to form esters, in the below reaction we are making ethyl ethanoate from ethanoic acid and ethanol.

Carboxylic acid + alcohol = ester + water

http://www.chemguide.co.uk/organicprops/alcohols/esterification.html 

Types of Carboxylic Acids

• Acetic Acid- Used in vinegar, gives it it’s sour taste. One of the simplest carboxylic acids.

• Tannic Acid- It is used for tanning, it is in a number of tree barks, it is used for staining wood and dying cotton.

• Salicylic Acid- used in acne creams, it is also used as a food preservative.

• Citric Acid- found in most citrus fruits, it is a natural preservative it is also found in bathroom and kitchen cleaners along with soft drinks.

• Malic Acid- this is found in many unripe fruits like green apples.

• Oxalic Acid- it is used in bleaching and cleansing solutions. This also appears in rhubarb leaves and is poisonous.

• Acetylsalicylic acid- Aspirinwww.leanitup.com 

Every day examples• Formic acid- found in ant venom• Butyric acid- commonly found in milk especially in goats

and buffalos. Smells good tastes awful. • Propionic acid- found in perennials (flowers that come

back every year) smells terrible but the esters of this acid smell lovely and are used in perfumes and cosmetics.

• Caproic acid- is a fatty acid and is commonly found in goats and other barnyard animals

• Enanthic acid- has a rancid oder and is commonly found in caster oils.

• Caprylic acid- smells terrible and is found in the milk of most mammals including humans.

• Pelargonic acid- smells awful and is used in making many liqures also used to make esters

• Capric acid- saturated fatty acid, found naturally in coconut oil.allthingsherbal.com  blog.findwell.com 

Other Facts

• Formic Acid was first prepared by the distillation of ants, the swelling and irritation caused by ant bites and bee stings comes from formic acid.

• Carboxylic acids are weak in water.• Carboxylic acids are also known as boxylic acids

and all have the same general formula.• These acids react together with alcohols to make

esters.• Carboxylic acids and their esters can be reduced to

alcohols by suitable reduction agents.• Carboxylic acids have a very pungent Oder

compared to esters pleasant aromas.

Lets Review

• Relationshttp://www.youtube.com/watch?v=xheOq0XZ-so

 • Naming scheme 

http://www.youtube.com/watch?v=z8h7QgevqjM 

Lemons for Losers!!!

• It’s game time, everyone in the class divide into two sides and pick one person as a team captain…

Just for an interesting ending point… never eat citric acid powder in large doses…

http://m.youtube.com/watch?v=fM9BgDJ01Cl&desktop_uri=%2Fwatch%3Fv%3DfM9BgDJ01Cl

 

www.delcraychem.com 

More cool tricks with carboxylic acids

• Orange peel flame thrower• http://www.youtube.com/watch?v=JycKEI8XZ

s8 

  

• vinigar, calcium hypochlorite, and sucrose.• http://www.youtube.com/watch?v=HTznU9nII

m0 

Sources

Book Sources:• Chemistry study of matter and its changes, Text book, author: 

Brady Holum• Chemistry Reactions, structure, and properties. Text Book, Authors: 

Clyde. R. Dillard, David. E. Goldberg• Chemistry, Text Book, Authors: Gillespie, Ronald J.Internet Sources:• http://colapret.cm.utexas.edu• http://en.wikipedia.org• http://humantouchofchemistry.com• http://youtube.com • www.inchem.org