Carboxylic Acids
By: Courtney and Amelie
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General Formula and Structure
• The general formula for a carboxylic acid is:
O
Cn H2n+1 COOH or R
C OH the R variable
representing the first part of the name.
O
EX: Methanoic acid
H
C OH
• The general structure for a carboxylic acid is:
AX₃ Planar
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
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Naming Scheme
• Double and Triple bonds
With 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 bond
Propane  Propen  Propenoic acid  2-Propenoic
acid
But 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.
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More Naming
Carbon 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
+
http://www.chemguide.co.uk/organicprops/alcohols/esterification.html
water
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- Aspirin
www.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
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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
• Relations
http://www.youtube.com/watch?v=xheOq0XZso
• Naming scheme
http://www.youtube.com/watch?v=z8h7Qgev
qjM
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=JycKEI8XZs8
• vinigar, calcium hypochlorite, and sucrose.
• http://www.youtube.com/watch?v=HTznU9nIIm0
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