CARBOXYLIC ACIDS By Dale & Cameron. GENERAL STRUCTURE A carboxylic acid is an organic acid that contains a carboxyl group. A carboxyl group is simply.

CARBOXYLIC ACIDSBy Dale & Cameron

GENERAL STRUCTURE

A carboxylic acid is an organic acid that contains a carboxyl group. A carboxyl group is simply a carbonyl group (one carbon atom double-bonded to a oxygen atom) attached to a hydroxyl group (hydroxide ion). The carbon is also connected to the rest of the hydrocarbon and the general formula is RCOOH (R is the rest of the hydrocarbon.)

Ex:

R-C-OH

O

GENERAL STRUCTURE (CONT.)

Methanoic Acid: Ethanoic Acid:

Propanoic Acid: Butanoic Acid:

NAMING SCHEME

The naming scheme for a carboxylic acid is pretty simple: replace the “e” ending of the parent alkane with the ending “oic acid”. The parent chain is the longest continuous carbon chain. That gives you the IUPAC name for the carboxylic acid but most of them also have common names that people call them everyday that aren’t quite as obvious.

Ex: Methane becomes Methanoic Acid, Ethane becomes Ethanoic Acid, etc.

NAMING SCHEME (CONT.)

Formula Carbon Atoms

IUPAC Name Common Name Melting Point (°C)

HCOOH 1 Methanoic Acid Formic Acid 8

CH3COOH 2 Ethanoic Acid Acetic Acid 17

CH3CH2COOH 3 Propanoic Acid Propionic Acid -22

CH3(CH2)2COOH 4 Butanoic Acid Butyric Acid -6

CH3(CH2)4COOH 6 Hexanoic Acid Caproic Acid -3

CH3(CH2)6COOH 8 Octanoic Acid Caprylic Acid 16

CH3(CH2)8COOH 10 Decanoic Acid Capric Acid 31

CH3(CH2)10COOH 12 Dodecanoic Acid Lauric Acid 44

CH3(CH2)12COOH 14 Tetradecanoic Acid Myristic Acid 58

CH3(CH2)14COOH 16 Hexadecanoic Acid Palmitic Acid 63

CH3(CH2)16COOH 18 Octadecanoic Acid Stearic Acid 70

REACTION PROPERTIES

There are several reactions that a carboxylic acid can be part of. One is water combining with ethanoic acid to make acetate and hydronium, another is combing magnesium and ethanoic acid to make hydrogen and magnesium acetate tetrahydrate, and a chemical reaction to make a carboxylic acid is to oxidize the corresponding aldehyde or to use an excess amount of oxidizer (such as potassium dichromate) to turn a primary alcohol into the corresponding carboxyl acid.

REACTION PROPERTIES (CONT.)

Ethanoic acid + Water Acetate + Hydronium

CH3COOH + H2O CH3COO + H3O

Ethanoic acid + Magnesium Magnesium Acetate Tetrahydrate + Hydrogen

CH3COOH + Mg Mg(CH3COO)2 + H2

Propanal + Potassium Dichromate Propionic Acid

CH3CH2CHO + K2Cr2O7 CH3CH2COOH

EVERYDAY USE

Carboxylic acids are called by their common names more often than their IUPAC names and are found in several places in everyday life. The lower-molar-mass carboxylic acids (Formic acid, acetic acid, propionic acid, etc.) are colourless, volatile liquids. The formation of acetic acid in wine is what turns wine into vinegar. Several carboxylic acids were first isolated from fats and are called fatty acids (propionic acid literally means first fatty acid). The higher-molar-mass carboxylic acids (Myristic acid, palmitic acid, stearic acid, etc.) are waxy, odorless solids with low melting points. Stearic acid, obtained from beef fat, is used to make wax candles. Some other examples are acetylsalicylic acid (aspirin) contains a carboxylic acid group, ascorbic acid is found in Vitamin C, citric acid is found in citrus fruits such as lemons or limes and oxalic acid is found in spinach and is called a dicarboxylic acid.

OTHER INFORMATION

Carboxylic acids are used as precursors to form other compounds such as esters, aldehydes and ketones. Carboxylic acids can form hydrogen bonds with themselves, especially in non-polar solvents, which makes them more stable and elevates their boiling points. Since they contain both hydroxyl groups and carbonyl groups, they can receive or give hydrogens for hydrogen bonding.

Jeopardy

Naming & Formulas

General Structure

Everyday Uses

Reactions General Information

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This carboxylic acid has the formula CH3COOH and is commonly known as acetic acid.

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What is ethanoic acid

Hexanoic acid is commonly known as what.

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What is caproic acid

The formula for propionic acid is what.

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What is CH3CH2COOH.

At what temperature (°C) does stearic acid melt.

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What is 70°C

What is the IUPAC naming rule for carboxylic acids.

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What is replace the “e” of the parent alkane with “oic acid”

By which atom is the carboxyl group connected to the rest of the hydrocarbon.

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What is the carbon atom.

A carboxyl group is made up of what two other groups.

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What is a carbonyl group and a hydroxyl group.

What is the definition of a carboxylic acid.

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What is an organic acid containing a carboxyl group.

The fact that carboxylic acids can form hydrogen bonds among themselves affects what about their boiling and melting points.

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What is it raises the boiling and melting points.

The hydroxyl and carbonyl groups in a carboxyl group give carboxylic acids what property when it comes to hydrogen bonding.

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What is it gives them the ability to give or receive hydrogen atoms.

Which acid is responsible for turning wine into vinegar.

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What is acetic acid.

Ascorbic acid is found in what vitamin.

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What is Vitamin C.

Carboxylic acids with a lower molar mass are described as what.

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What is a colourless, volatile liquid.

Most carboxylic acids were first isolated from what substance.

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What is fat.

Stearic acid, a waxy, odorless solid is used to make what everyday item.

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What is a wax candle.

A reaction between ethanoic acid and water gives you acetate and what substance.

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What is hydronium.

Using an excess amount of oxidizer, you can get a carboxylic acid from what.

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What is a corresponding primary acid.

A reaction between a carboxylic acid and what type of element leaves you with a hydrogen molecule.

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What is a metal.

What is Potassium Dichromate an example of.

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What is an oxidizer.

By what process does an aldehyde become a carboxylic acid.

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What is oxidization.

A carboxylic acid can perform what with another carboxylic acid.

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What is hydrogen bonding.

Carboxylic acids are used as precursors to form compounds such as esters, aldehydes and what.

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What are ketones.

Hydrogen bonding elevates the boiling point of carboxylic acids as well as what.

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What is increase their stability.

What gives carboxylic acids the ability to receive and give hydrogen atoms.

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What are carbonyl and hydroxyl groups.

In what substance is hydrogen bonding the most common among carboxylic acids.

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What is non-polar solvents.

BIBLIOGRAPHY

Gillespie, Ronald, Humphreys, David, Baird, N. Colin, and Robinson, Edward. “Section 19.5: Carboxylic Acid” Chemistry. Massachusetts, 1986. Print.

Wilbraham, Anthony, Staley, Dennis, Matta, Michael, and Waterman, Edward. “Section 23.3: Carbonyl Compounds. P. 740-741.” Prentice Hall Chemistry. Massachusetts: Pearson Education Inc., 2008. Print.

“Carboxylic Acids” www.boundless.com/chemistry/textbooks/boundless-chemistry-textbook/organic-chemistry-23/functional-group-names-properties-and-reactions-166/carboxylic -acids-641-3673/

Clark, Jim. www.chemguide.co.uk/organicprops/acids/acid.ty.html#top. 2004.