Ch. 10 - Anticoagulant, water treatments, and fragrances.

Carboxylic Group

Describes the functional groups of carboxylic acids (—OH) and Ethers (-OR)

Acyl groups of the Carboxylic acid group can also attach to what? In addition to ‐OH and –OR?

A variety of electronegative atoms

(Halides, nitrogen, sulfur)

What is this structure depicting?

Carboxylic Acid

Thioesters are important to the _______ that takes place during the Krebs cycle

Acyl transfer

Carboxylic Acids

1. Posses at least one –COOH group

2. The name comes from carbonyl (–CHO) and hydroxyl (–OH)

Why are Carboxylic acids considered weak acids?

It only partially dissociates in water when it forms a conjugate base and Hydronium ion

The only acidic hydrogen on an organic acid is the hydrogen associated with the ______

Oxygen atom

In carboxylic acids the ______ is much more electronegative than the hydrogen

Oxygen atom

Naming carboxylic acids

1. Derived from Alkanes

2. –e ending replaced with –Oic acid

Known as fatty acids because they occur naturally in fats

Carboxylic acids

HCOOH

Formic acid (Methanonic acid)

CH³COOH

Acetic acid (Ethanoic acid)

CH3CH2COOH

Propionic acid (propanoic acid)

CH3CH2CH2COOH

Butyric acid (Butanoic acid)

CH3CH2CH2CH2COOH

Valeric acid (pentanoic acid)

Formic acid

Occurs naturally in some ants. Formica(ant)

Acetic acid

Diluted is in household vinegar

Propionic acid

Body odor, one of the first fatty acids identified

Butyric acid

Isolated from butter

Valeric acid

Extracted from the plant valerian

In the presence of strong bases (sodium hydroxide) carboxylic acids are completely _______ in a double replacement effect style reaction

Neutralized

Metal carboxylate

1. Identified by naming the metal

2. followed by changing the —ic acid of the carboxylic acids to –ate

HCOONa

Sodium formate

CH3COONa

Sodium acetate

CH3CH2COONa

Sodium propionate

CH3CH2CH2COONa

Sodium Butanonate (butyrate)

CH3CH2CH2CH2COONa

Sodium Valerate

Sodium formate

Common Food additive

Sodium Benzoate

• Preservative in acidic food

• Medicine

• Cosmetics

Sodium Acetate

Seasoning

_______are used as anticoagulant and water conditioners

Sodium carboxylates

Polycarbonate acids

2 or more carboxylic groups are in one molecules

Corresponding metal carboxylates used in embalming water treatments

Dicarboxylic acids

Analogous to dialcohols and Dialdehydes

Simplest dicarcoxylic acid

Oxalic Acid

HOOC-COOH

Oxalic acid

HOOC-CH2-COOH

Malonic acid

HOOC-CH2CH2-COOH

Syccinic acid

HOOC-CH2CH2CH2CH2‐COOH

Adiptic acid

Oxalic acids can be completely neutralized in the presence of a strong_____

Base

Dimetaloxalate

Product of neutralization of sodium oxalate

Role of water softening agent and anticoagulant

Sodium oxalate has the ability to _______ calcium ions

Gather together

When soluble, sodium oxalate is a _______ in embalming fluid

Modifying agent

Sodium Oxalate is classified as what kind of anticoagulant?

Precipitant anticoagulant

Precipitant anticoagulant

Removes calcium ions via precipitation. Removes calcium as a potential blood clotting initiator

What structure is this depicting?

Sodium Oxalate

What structure is this showing?

Oxalic acid

Tricarboxylic acid

1. 3 carboxylic acids groups and Hydroxyl group

2. Common way to remove solid water deposits is to add vinegar (a tricarboxylic acid)

Sequestrant anticoagulant

Cages in the calcium ions making it unavailable to coagulate blood

Types of tricarboxylic acids

1. Citric acid

2. Potassium citrate

3. Sodium citrate

What tricarboxylic acids are sequestrant?

Potassium cirate and sodium cirate.

Why have potassium citrate and sodium cirate gone out of favor for anticoagulation?

They can actually increase clotting by promoting bacteria

EDTA (ethylenediaminetetraacetic acid)

• "Colorless, water soluble, poly carboxylic acids

• Ability to sequester metal ions

• Hexadentate ligand

• Great sequestrant anticoagulant

• Important ingredient in embalming fluid

• Cleating agent

Chelation

The formation of at least two coordinate bonds between a central metal and an organic ligand

After being bound by EDTA metal ions remain in solution but have little to no ______

Reactivity

What organic molecule is used as anticoagulant and water conditioners today?

EDTA. No harmful effects. Used in medicine for chelation therapy for treating for treatment of mercury and least poisoning

What structure is this showing?

EDTA

Esters

Formed by combining a carboxylic acid with an alcohol (esterfication reaction)

High molecular Mass esters (glycerides)

• Make up main class

• Animal fats, veg oils

Lower molecular weight esters

Pheromones

Naming esters

• Name alkyl group attached to oxygen

• Change -ic acid to ate

Methyl Salicylate (fragrance)

Possess both phenol and esters function

• Wintergreen scent

• Precipiant anticoagulant

Thioester

Linking oxygen replaced by sulfur (Sulfur has same number of valence electrons as oxygen)

Naming thioesters

Named as if the alkyl chain from the alcohol is a substitutent

No number assigned to alkyl chain

Followed by the name of the parent chain (acetate)

Named as alkane w/Thioate

Prepared by reaction of a carboxylic acid with a thioalcohol (mercaptan)

Thioesters

How are thioesters important?

They are important biologically. Krebs cycle. Acetyl-CoA and how we get ATP