PHPOrgChem (Lecture) | Module 7: (Part 1: ALCOHOLS, PHENOLS, and THIOLS ONLY)

Alcohol

Contain the hydroxyl (-OH) group.

Ethanol

ALCOHOLS: found in antiseptics and alcoholic beverages

Primary Alcohol, Secondary Alcohol, and Tertiary Alcohol

Alcohols are classified as?

Primary Alcohol

ALCOHOLS CLASSIFICATION: -OH attached to a carbon with one other carbon.

Primary Alcohol

ALCOHOLS CLASSIFICATION: Ex.: Ethanol & Methanol

Primary Alcohol

ALCOHOLS CLASSIFICATION: Attached to one alkyl group and/or hydrogen

Primary Alcohol

ALCOHOLS CLASSIFICATION: More reactive

Primary Alcohol

ALCOHOLS CLASSIFICATION:

Primary Alcohol

ALCOHOLS CLASSIFICATION:

Secondary Alcohol

ALCOHOLS CLASSIFICATION: -OH attached to a carbon with two other carbons.

Secondary Alcohol

ALCOHOLS CLASSIFICATION: Ex. 2-propanol

Secondary Alcohol

ALCOHOLS CLASSIFICATION:

Tertiary Alcohol

ALCOHOLS CLASSIFICATION: -OH attached to a carbon with three other carbons.

Tertiary Alcohol

ALCOHOLS CLASSIFICATION: Ex.: 2-methyl-2-propanol

Tertiary Alcohol

ALCOHOLS CLASSIFICATION:

Polar

PHYSICAL PROPERTIES: Alcohols are ____ due to the hydroxyl (-OH) group.

Water

PHYSICAL PROPERTIES: Alcohol are polar, ethanol can easily dissolve in ____

Shorter

PHYSICAL PROPERTIES: Alcohols can mix well with water esp. those with ______ carbon chain

Inversely Proportional

PHYSICAL PROPERTIES: Solubility of Alcohol decreases as carbon chain length increases (____________)

Hydrogen

PHYSICAL PROPERTIES: Alcohols can form ________ bonds

Alkanes

PHYSICAL PROPERTIES: Alcohols have higher boiling points than ______, due to strong Hydrogen bonding

More Heat

PHYSICAL PROPERTIES: Alcohol and water require ________ to evaporate

Less

PHYSICAL PROPERTIES: Alcohol is _____ dense than water

Colorless

PHYSICAL PROPERTIES: What is the color of the liquid (Alcohol)?

Sweet

PHYSICAL PROPERTIES: Alcohols have mild, sometimes ____ smell

Weak

PHYSICAL PROPERTIES: Alcohols are _____ acid → can donate Hydrogen ion but not as easily like acetic acid

Acetic Acid

PHYSICAL PROPERTIES: Alcohols are weak acid → can donate Hydrogen ion but not as easily like?

Oxidation

REACTIONS WHERE ALCOHOLS UNDERGO: one of their most useful properties

ALDEHYDES, KETONES, or CARBOXYLIC ACID

REACTIONS WHERE ALCOHOLS UNDERGO: Depending to the structure of the alcohol, oxidation can produce?

Primary Alcohol

OXIDATION OF ALCOHOLS: ________ → Aldehydes → Carboxylic acids.

Second Alcohol

OXIDATION OF ALCOHOLS: _______ → Ketones.

Tertiary Alcohol

OXIDATION OF ALCOHOLS: ________ → resist oxidation.

Ethanol

REACTIONS WHERE ALCOHOLS UNDERGO: Oxidation of _____ in the liver → produces acetaldehyde → responsible for hangover symptoms

Acetaldehyde

REACTIONS WHERE ALCOHOLS UNDERGO: Oxidation of ethanol in the liver → produces ________ → responsible for hangover symptoms

Combustion

REACTIONS WHERE ALCOHOLS UNDERGO: Can BURN IN OXYGEN producing CARBON DIOXIDE AND WATER in a process called?

Carbon Dioxide, and Water

REACTIONS WHERE ALCOHOLS UNDERGO: Alcohols can burn in oxygen producing?

Ethanol

COMBUSTION OF ALCOHOLS: This undergo combustion → product is used in biofuels

Dehydrated

REACTIONS WHERE ALCOHOLS UNDERGO: Can be ______ (LOSE WATER) to form ALKENES when treated with strong acids

Carboxylic Acid

REACTIONS WHERE ALCOHOLS UNDERGO: Can react with ___________ TO FORM ESTERS in a process called ESTERIFICATION

Esters

REACTIONS WHERE ALCOHOLS UNDERGO: Can react with Carboxylic Acid to form this

Propranolol

1-NAPHTHALEN-1-YLOXY-3-(PROPAN-2-YLAMINO)PROPAN-2-OL is also known as?

Propranolol

EXAMPLES OF DRUGS CONTAINING ALCOHOLS: ANTIHYPERTENSIVE MEDICATION (Beta-Blocker)

Secondary Alcohol

EXAMPLES OF DRUGS CONTAINING ALCOHOLS: What is the classification of the alcohol in Propranolol?

Water

EXAMPLES OF DRUGS CONTAINING ALCOHOLS:
SOLUBILITY: The alcohol group makes propranolol dissolves well in ____, helping it to be absorbed into the bloodstream and reach its target site

Liver

EXAMPLES OF DRUGS CONTAINING ALCOHOLS:
METABOLISM: drug metabolize in the _____ where the alcohol group influence how long the drug last in the body, and how quickly it is broken down

Extreme Conditions

EXAMPLES OF DRUGS CONTAINING ALCOHOLS:
STABILITY: The alcohol group helps maintain propranolol stability when stored properly, but ___________ can affect effectiveness (air exposure → when the drug is opened and exposed to air/moisture)

Blood-brain barrier

EXAMPLES OF DRUGS CONTAINING ALCOHOLS:
EFFECTIVENESS:
Alcohol group allows propranolol to cross the?

Propranolol

EXAMPLES OF DRUGS CONTAINING ALCOHOLS: Use to treat anxiety & heart conditions by acting on the heart and brain

Stage Fright

EXAMPLES OF DRUGS CONTAINING ALCOHOLS: Before, propranolol is use only for heart conditions, but now, propranolol can be used for?

Albuterol

EXAMPLES OF DRUGS CONTAINING ALCOHOLS: Name of SALBUTAMOL used in US/western countries

Salbutamol

EXAMPLES OF DRUGS CONTAINING ALCOHOLS: “ALBUTEROL” (name used in US/western countries)

Salbutamol

EXAMPLES OF DRUGS CONTAINING ALCOHOLS: Alcohol helps it dissolve in water and be effective in treating asthma and other respiratory conditions by improving absorption and delivery into the lungs.

Bronchodilator

EXAMPLES OF DRUGS CONTAINING ALCOHOLS:
EFFECTIVENESS: Alcohol group aids in the drugs’ ability to reach its target in the lungs

• Where it works as _________ to relax the muscle in the airways helping to ease breathing

Phenol

A TYPE OF ARENE WITH ALCOHOL GROUP

Phenol

Differs from alcohol because of their hydroxyl group (-OH) is attached to an aromatic ring (arene) which makes them more stable, and more acidic compared to alcohol

More Stable, and More Acidic

PHENOL: Differs from alcohol because of their hydroxyl group (-OH) is attached to an aromatic ring (arene) which makes them __________, and __________ compared to alcohol

Arene

a cyclic ring with six carbons and alternating double bonds, which make them more stable and more acidic.

Phenol

More acidic than alcohols due to resonance stabilization.

Phenol

Used in disinfectants and pain relievers

Phenol

are special type of organic compounds where the hydroxyl group is directly attached to a benzene ring

Polar

PHYSICAL PROPERTIES: ____- due to the hydroxyl (-OH) group attached to an aromatic benzene ring.

Phenol

PHYSICAL PROPERTIES: They mix somewhat with water but their SOLUBILITY IS LOWER compared to small alcohols like ethanol, however they DISSOLVE WELL IN ORGANIC SOLVENTS

Lower

PHYSICAL PROPERTIES: Phenols mix somewhat with water but their SOLUBILITY IS ______compared to small alcohols like ethanol, however they DISSOLVE WELL IN ORGANIC SOLVENTS

Organic Solvents

PHYSICAL PROPERTIES: Phenols mix somewhat with water but their SOLUBILITY IS LOWER compared to small alcohols like ethanol, however they DISSOLVE WELL IN?

Phenol

PHYSICAL PROPERTIES: Unlike regular alcohols, they have HIGHER BOILING POINTS because they form STRONG HYDROGEN BOND, making them HARDER TO EVAPORATE

Strong Hydrogen Bond

PHYSICAL PROPERTIES: Unlike regular alcohols, Phenols have HIGHER BOILING POINTS because they form ___________________, making them HARDER TO EVAPORATE

Moderately Soluble

PHYSICAL PROPERTIES: Phenols are _____________ in water but MORE SOLUBLE in organic solvents.

Non-Polar

PHYSICAL PROPERTIES: Solubility of Phenols decreases as the benzene ring gets substituted with more ______ groups.

Slightly Denser

PHYSICAL PROPERTIES: Phenols are usually ___________ than water

Colorless to Light Pink Solid or Liquid

PHYSICAL PROPERTIES: Color and States of Phenols

Strong Sharp Smell

PHYSICAL PROPERTIES: Smell of Phenols that are often described as medicinal or slightly burnt

Phenol

CHEMICAL PROPERTIES: They are MORE ACIDIC than regular alcohols

Phenol

CHEMICAL PROPERTIES: They can easily donate hydrogen ions because the benzene ring helps stabilize the negative charge that forms when the hydrogen is lost

Resonance Stabilization

CHEMICAL PROPERTIES: Stronger acid than alcohols due to the ______________ of its conjugate base

Conjugate Base

CHEMICAL PROPERTIES: Phenols are stronger acid than alcohols due to the resonance stabilization of its?

Phenol

CHEMICAL PROPERTIES: Forms esters with acids (e.g., esterification with acetic acid)

Strong Bases

CHEMICAL PROPERTIES: This acidity also allows phenols to REACTS WITH ___________ like sodium hydroxide which forms phenoxide ions which increase their solubility in water

Phenoxide Ions

CHEMICAL PROPERTIES: This acidity also allows phenols to REACTS WITH STRONG BASES like sodium hydroxide which forms ____________ which increase their solubility in water

Phenoxide Ions

CHEMICAL PROPERTIES: These ions increase solubility in water (Phenols)

Phenol

CHEMICAL PROPERTIES: They also undergo Oxidation forming compounds QUINONES

Quinones

CHEMICAL PROPERTIES: Phenols forms this and they are useful in biological activities and industry process

Highly Reactive

CHEMICAL PROPERTIES: Because of the (-OH) group of Phenols, the BENZENE RING in phenol, is __________, making it easier for phenols to undergo electrophilic substitution reaction (e.g., halogenation, nitration)

Electrophilic Substitution Reaction

CHEMICAL PROPERTIES: Because of the (-OH) group of Phenols, the BENZENE RING in phenol, is HIGHLY REACTIVE, making it easier for phenols to undergo _______________________

Electrophilic Substitution Reaction

CHEMICAL PROPERTIES: In Phenols, different atoms/group like HALOGENS OR NITROGEN GROUPS, can easily replace hydrogen atoms in the benzene ring, leading to the formation of important derivatives like antiseptics and disinfectants

Halogens, or Nitrogen Groups

CHEMICAL PROPERTIES: In Phenols, Electrophilic Substitution Reaction consists of different atoms/group like ___________ OR __________________, can easily replace hydrogen atoms in the benzene ring, leading to the formation of important derivatives like antiseptics and disinfectants

Epinephrine

4-[(1R)-1-HYDROXY-2-(METHYLAMINO)ETHYL]BENZENE-1,2-DIOL is also known as?

Epinephrine

EXAMPLES OF DRUGS CONTAINING PHENOLS: Used in ANAPHYLAXIS OR ASTHMA ATTACK

Anaphylaxis, or Asthma Attack

EXAMPLES OF DRUGS CONTAINING PHENOLS: Epinephrine are used in?

Allergic Reaction

Anaphylaxis is also known as?

Bacterial Growth

EXAMPLES OF DRUGS CONTAINING PHENOLS: Phenol PREVENTS ________ in epinephrine solutions keeping them safe for used overtime

Preservative

EXAMPLES OF DRUGS CONTAINING PHENOLS: Phenols acts as a ______ agent

Potent

EXAMPLES OF DRUGS CONTAINING PHENOLS: Epinephrinecan degrade when exposed oxygen/air, light, or heart. phenol can SLOW BREAKING DOWN, ensuring the drug to remain __________ for the long period of time

Contamination, and Degradation

EXAMPLES OF DRUGS CONTAINING PHENOLS: In short, phenols helps to keep epinephrine effective and safe by preventing __________ and slowing its ________

Propofol

2,6-DIISOPROPYLPHENOL is also known as?

Propofol

EXAMPLES OF DRUGS CONTAINING PHENOLS: Used as an ANESTHETIC AGENT (milk-like)

Emulsion

EXAMPLES OF DRUGS CONTAINING PHENOLS: Propofol is a _________ BASED DRUG (IN VIAL), meaning it can support bacterial growth

Antimicrobial

EXAMPLES OF DRUGS CONTAINING PHENOLS: Phenol acts as a ____________ AGENT, preventing contamination and making the drug safer for the repeated used

Antimicrobial

EXAMPLES OF DRUGS CONTAINING _____________ AGENT, preventing contamination and making the drug safer for the repeated used

Epinephrine

EXAMPLES OF DRUGS CONTAINING PHENOLS: In short, phenols helps to keep ___________ effective and safe by preventing contamination and slowing its degradation

Propofol

EXAMPLES OF DRUGS CONTAINING PHENOLS: In short, phenol in _____ keeps it free from harmful microbes and help it maintain its potency overtime