W15: CARBOXYLIC ACIDS

A ____________ is an organic compound whose functional group is the carboxyl group.

carboxylic acid

A ____________ is a carbonyl group (CO) with a hydroxyl group (—OH) bonded to the carbonyl carbon atom.

carboxyl group

Abbreviated linear designations for the carboxyl group are:

The __________________ has a hydrogen atom attached to the carboxyl group carbon atom.

simplest carboxylic acid

Draw the structure of simplest carboxylic acid:

The structure of the _______________________________ involves a benzene ring to which a carboxyl group is attached.

simplest aromatic carboxylic acid

Is an organic compound that can be synthesized from or converted into a carboxylic acid.

Carboxylic derivatives

Four important families of carboxylic acid derivatives are:

1.) Esters
2.) Acid chlorides
3.) Acid Anhydrides
4.) Amides

Draw structure of Ester:

Draw the structure of Acid chloride

Draw the structure of acid anhydride

Draw the structure of Amide:

A __________________ is a carboxylic acid in which one carboxyl group is present.

monocarboxylic acid

In naming monocarboxylic acid, name the parent chain by changing the -e
ending of the corresponding alkane to __________.

-oic acid

What are the three simplest carboxylic acids?

1.) Methanoic acid
2.) athanoic acid
3.) propanoic acid

Draw the structure of Methanoic acid:

Draw the structure of Ethanoic acid:

Draw the structure of Propanoic acid:

Is a carboxylic acid that contains two carboxyl groups, one at each end of a carbon chain.

Dicarboxylic acids

The simplest aromatic carboxylic acid is called __________.

benzoic acid

Draw the structure of benzoic acid:

It is the stinging sensation associated with red ant bites.

Formic acid

Vinegar contains small amount of _____ acid

acetic

Is the smallest acid that can be obtained from fats

Propionic acid

Component of a rancid butter.

Butyric acid

Found in valerian foot, it has a strong odor.

Valeric acid

Skin secretions of goat

Caproic acid

It is the “most” widely used of all carboxylic acids.

Acetic acid

It is the simplest carboxylic acid, found in plants.

Oxalic acid

Play important roles in biochemical reactions that occur in the human body.

Succinic and Glutaric acid

Is a carboxylic acid that contains one or more additional functional groups besides one or more carboxyl groups.

Polyfunctional carboxylic acids

Three commonly encountered types of polyfunctional carboxylic acids are:

1.) Unsaturated acids
2.) Hydroxy acids
3.) Keto acids

Draw the structure of an unsaturated acid:

Draw the structure of hydroxy acid:

Draw the structure of a keto acid:

This is the simplest unsaturated mono carboxylic acid.

Propenoic acid

Unsaturated acid trans isomer

Fumaric acid

Unsaturated acid Cis isomer

Maleic acid

Four simpler hydroxy acids are:

1.) Glycolic acid
2.) Lactic acid
3.) Malic acid
4.) Tartaric acid

Is present in the juice from sugar cane and sugar beets

Glycolic acid

Is present in sour milk, sauerkraut, and dill pickles.

Lactic acid

Occurs naturally in fruits.

Malic acid and Tartaric acid

Sharp taste of the apple.

Malic acid

Abundant in grapes, component of tartar sauce, and acidic ingredients in many baling ingredients.

Tartaric acid

The best known of all carboxylic acids. Gives citrus fruits their sharp
taste, widely used in beverages and foods. Tricarboxylic acid.

Citric acid

As the designation implies, contain a carbonyl group within a carbon chain.

Keto acid

With three carbon atoms, is the simplest keto acid that can exist.

Pyruvic acid

Carboxylic acids are the most ___________ compounds

polar organic

Both the carbonyl part and the hydroxyl of the carboxyl functional group are ________.

polar

The result is very ____________________ for carboxylic acids, the highest of any type of organic compound yet considered.

high melting and boiling points

Unsubstituted saturated monocarboxylic acids containing up to _______________ are liquids that have strong, sharp odors

nine carbon atoms

Acids with ____________________ in an unbranched chain are waxy solids that are odorless (because of low volatility).

10 or more carbon atoms

Aromatic carboxylic acids, as well as dicarboxylic acids, are also ________________________.

odorless solids

The high boiling points of carboxylic acids indicate the presence of ____________________________________.

strong intermolecular attractive forces

Carboxylic acids readily hydrogen-bond to _____________.

water molecules

Such hydrogen bonding contributes to water solubility for ____________ carboxylic acids.

short-chain

Oxidation of _____________ or __________, using an oxidizing agent such as ________ or ___________, produces carboxylic acids.

1.) primary alcohols
2.) aldehydes
3.) CrO3
4.) K2Cr2O7

Aromatic acids can be prepared by oxidizing a _______________ on a _____________.

1.) carbon side chain
2.) benzene derivative

Is a carboxylic acid derivative in which the —OH portion of the carboxyl group, has been replaced with an —OR group.

Ester

In linear form, the ester functional group can be represented as:

COOR or -CO2R