PHPOrgChem (Lecture) | Module 7: (Part 2: ETHERS, and THIOETHERS ONLY)

Ether

CONTAIN AN OXYGEN ATOM BONDED TO TWO CARBON ATOMS (ALKYL OR ARYL GROUPS)

Ether

General formula: R-O-R' (R and R represents carbon containing groups like alkyl chains or aromatic rings)

Ether

They are commonly used as SOLVENTS and FUEL additives.

Ether

Have LOW REACTIVITY compared to alcohols.

Diethyl Ether

EXAMPLES OF DRUGS CONTAINING ETHERS: used as an anesthetic.

Slightly Polar

PHYSICAL PROPERTIES: Ethers are __________ due to the oxygen atom, but they are LESS POLAR THAN ALCOHOLS because they lack the hydroxyl (-OH) group.

Alcohols

PHYSICAL PROPERTIES: Ethers are SLIGHTLY POLAR due to the oxygen atom, but they are LESS POLAR THAN ________ because they lack the hydroxyl (-OH) group.

Boiling Points

PHYSICAL PROPERTIES: Ethers have relatively low ________________ compared to alcohols of similar molecular weight, as they DO NOT FORM HYDROGEN with each other bonds like alcohols

Moderately Soluble

PHYSICAL PROPERTIES: Ethers are _______________ IN WATER but their solubility decreases as the size of the alkyl groups attached to the oxygen atom increases. They are also good solvents for many organic compounds.

Lower

PHYSICAL PROPERTIES: Ethers tend to have a ______ DENSITY THAN WATER, which is why they float when mixed with water.

Colorless

PHYSICAL PROPERTIES: Color of Ethers

Pleasant, Slightly Sweet Smell

PHYSICAL PROPERTIES: Smell of Ethers

Perfume

PHYSICAL PROPERTIES: Ethers were once used in the ______ industry. Now, they are commonly used as solvents in the laboratory

Stable, and Inert

CHEMICAL PROPERTIES: Ethers are relatively ______, and _____, meaning they do not readily react with most chemicals under normal conditions.

Solvent

CHEMICAL PROPERTIES: Because ethers are relatively stable, and inert, they are useful as _____ for wide range of chemical reactions

Alkyl Halides

CHEMICAL PROPERTIES: Ethers can REACT WITH HALOGENS like chlorine or bromine under certain conditions to form?

Highly Flammable

CHEMICAL PROPERTIES: Ethers are _____________, especially in the presence of air or heat.

Cleavage

CHEMICAL PROPERTIES: One of the important chemical properties of ether

Cleavage Reactions

CHEMICAL PROPERTIES: Ethers can undergo ______________ when exposed to strong acids, heat, and flame, breaking the bond between the oxygen, and the two alkyl groups.

Oxygen, and the Two Alkyl Groups

CHEMICAL PROPERTIES: Ethers can undergo CLEAVAGE REACTIONS when exposed to strong acids, heat, and flame, breaking the bond between the?

Cleavage Reactions

CHEMICAL PROPERTIES: This reaction involves breaking down of oxygen and carbon bonds, splitting the ether into two smaller parts

Peroxides

CHEMICAL PROPERTIES: Ethers are generally RESISTANT TO OXIDATION, BUT CAN FORM?

Unstable

CHEMICAL PROPERTIES: Ether has a tendency to form peroxides, which are ________ compounds when exposed to light and air

Peroxides

CHEMICAL PROPERTIES: These __________can be dangerous because they are explosives like epoxides. That's why Ether is stored carefully to avoid this reaction

Enflurane

2-CHLORO-1-(DIFLUOROMETHOXY)-1,1,2-TRIFLUOROETHANE is also known as?

Enflurane

EXAMPLES OF DRUGS CONTAINING ETHERS: Volatile anesthetic

Volatile

EXAMPLES OF DRUGS CONTAINING ETHERS: Since enflurane is an anesthetic that needs to be in gaseous state to be inhaled, ether group helps KEEP THE DRUG ____________, which makes it able to evaporate easily at room temperature. Making it easier to administer as a gas during surgery

Stabilize

EXAMPLES OF DRUGS CONTAINING ETHERS: Ether Structure help _________ the molecule

Codeine

3-METHYLMORPHINE is also known as?

Opioid

Means it is use to treat pain

Codeine

In early times it is used to treat cough

Absorption

EXAMPLES OF DRUGS CONTAINING ETHERS: Ether can IMPROVE ___________ and distribution of codeine

Lipid Solubility

EXAMPLES OF DRUGS CONTAINING ETHERS: ENHANCE _____________ allowing it to be easily absorbed in the body and distributed to the target areas such as the brain for relief.

Lipophilic

Blood Brain Barrier is ________, drugs need to be lipid soluble to take effect in the brain

Degradation

EXAMPLES OF DRUGS CONTAINING ETHERS: Codeine, Ether group PROTECT the drug from __________ when exposed to environmental factors like light, moisture, and heat

• Ensure it remains POTENT AND EFFECTIVE for a long period of time

Sulfides

Also known as Thioethers

Thioethers

CONTAIN A SULFUR ATOM BONDED TO TWO ALKYL OR ARYL GROUPS

Thioethers

Similar to ethers, but with sulfur (S) replacing oxygen (O)

Thioethers

Have a stronger odor due to sulfur.

Thioethers

Found in biological molecules (e.g., methionine, an amino acid).

Thioethers

PHYSICAL PROPERTIES: They are generally LESS POLAR THAN ALCOHOLS as Sulfur is less electronegative than Oxygen BUT MORE POLAR THAN HYDROCARBONS due to the but not as much as alcohols.

Weaker Bonding

PHYSICAL PROPERTIES: Thioethers HAVE HIGHER BOILING POINT THAN HYDROCARBONS BUT LOWER THAN ALCOHOLS of similar size due to the _____________ compared to alcohols.

Slightly Soluble

PHYSICAL PROPERTIES: Thioethers are _______________ IN WATER but dissolve well in organic solvents.

Organic Solvents

PHYSICAL PROPERTIES: Thioethers dissolves well in?

Lower

PHYSICAL PROPERTIES: Thioethers tend to have a ______ DENSITY THAN WATER and often float when mixed with water.

Colorless, or Pale Yellow

EXAMPLES OF DRUGS CONTAINING ETHERS: Color of Thioethers

Strong, Sulfur-Like, Unpleasant Odor

EXAMPLES OF DRUGS CONTAINING ETHERS: Odor of Thioethers

Stable

CHEMICAL PROPERTIES: Thioethers are GENERALLY CHEMICALLY ______ (QUITE INERT) and do not easily react with most substances under normal conditions.

Alkyl, or aryl halides

CHEMICAL PROPERTIES: Thioethers can REACT WITH HALOGENS like chlorine and bromine to form?

Sulfoxides, and Sulfones

CHEMICAL PROPERTIES: (when exposed to oxidizing agents) Thioethers can be OXIDIZED TO FORM ___________, AND _________, which are useful in various chemical and industrial applications/processes.

Highly Flammable

CHEMICAL PROPERTIES: Flammability of Thioethers

Nucleophilic Substitution Reactions

CHEMICAL PROPERTIES: (interesting feature) The SULFUR ATOM IS MORE NUCLEOPHILIC THAN OXYGEN in ethers, meaning thioethers CAN EASILY PARTICIPATE IN?

Omeprazole

6-METHOXY-2-[(R)-(4-METHOXY-3,5-DIMETHYLPYRIDIN-2-YL)M ETHYLSULFINYL]-1H-BENZIMIDAZOLE is also known as?

Omeprazole

• ANTACID OR USED TO TREAT ACID REFLUX

• STOMACH ULCER

Degradation

EXAMPLES OF DRUGS CONTAINING THIOETHERS: In Omeprazole, Thioethers help to PROTECT FROM ________. PROTECT FROM BREAKING DOWN too quickly in the body

Acidic

EXAMPLES OF DRUGS CONTAINING THIOETHERS: Omeprazole is sensitive to ________ condition (w/enteric coating), thioether helps stabilizes the molecule, preventing premature degradation, allowing it to work effectively when it reaches the stomach (so it can reach the small intestine)

Small Intestine

EXAMPLES OF DRUGS CONTAINING THIOETHERS: Omeprazole is sensitive to acidic condition (w/enteric coating), thioether helps stabilizes the molecule, preventing premature degradation, allowing it to work effectively when it reaches the stomach (so it can reach the ________________)

Lipid Solubility

EXAMPLES OF DRUGS CONTAINING THIOETHERS: In Omeprazole, Improve _____________ → Easy to pass the cell membrane

Stomach Lining

EXAMPLES OF DRUGS CONTAINING THIOETHERS: In Omeprazole, Help in ABSORPTION AND TO REACH THE TARGET SITE (__________) where it can block acid production

Thioguanine

CHEMOTHERAPY DRUG used to treat types of cancer

Enzyme Interaction

EXAMPLES OF DRUGS CONTAINING THIOETHERS: In Thioguanine, it ENHANCES ____________ → Sulfur atom in the thioether group enhances the drugs’ ability to interact with its target: ENZYMES INVOLVED IN DNA SYNTHESIS more effectively. This makes thioguanine more potent in blocking the growth and division of cancer cells.