PHPOrgChem (Lecture) | Module 7: (Part 3: REACTIONS OF ALCOHOLS, PHENOLS,THIOLS , ETHERS AND THIOETHERS)

Oxidation Reaction

REACTIONS OF ALCOHOL: It is a reaction where a molecule loses electrons/hydrogen and gains oxygen

Oxidation Reaction

REACTIONS OF ALCOHOL:

HYDROXYL GROUP

OXIDATION OF ALCOHOL: The _________________ is replaced by a CARBONYL GROUP

Oxidizing Agents

OXIDATION OF ALCOHOL: The presence of _____________ removes hydrogen from the (-OH) group and from the adjacent carbons.

Primary Alcohols

OXIDATION OF ALCOHOL: They are oxidized further further to CARBOXYLIC ACIDS

Methanol

OXIDATION OF ALCOHOL:
Example: _________ (Primary Alcohols)

• They first turn to ALDEHYDES (which has the carbonyl group: C=O), when oxidation continues they became CARBOXYLIC ACIDS like vinegars

Secondary Alcohols

OXIDATION OF ALCOHOL: Stops at KETONE

Isopropanol

OXIDATION OF ALCOHOL:

Example: __________ (Secondary Alcohols)

• Stops at the KETONE STAGE (which also has the C=O group) and DOES NOT OXIDIZED FURTHER

Oxidation Reaction

REACTIONS OF ALCOHOL: When alcohols reacts they can lose hydrogen or gain oxygen in a process called?

Oxidation Reaction

REACTIONS OF ALCOHOL: This happens when special chemicals or oxidizing agents like potassium dichromate in acid removes hydrogen from the alcohol molecule

Oxidation Reaction

REACTIONS OF ALCOHOL: In short, this reaction changes alcohols by replacing their hydroxyl group (-OH) with a carbonyl group (C=O) and how far they change depends on the type of alcohol present.

Dehydration Reaction

REACTIONS OF ALCOHOL: It is a reaction where a molecule loses water to form a double bond

Double Bond

REACTIONS OF ALCOHOL: Dehydration is a reaction where a molecule loses water to form a?

Dehydration Reaction

REACTIONS OF ALCOHOL:

• The acid (sulfuric acid) protonates (add proton) the (-OH) group making it a good leaving group

• The beta hydrogen from the adjacent carbon (neighboring carbon) is removed forming a double bond (alkene C=C)

Esterification Reaction

REACTIONS OF ALCOHOL: It is a reaction between alcohol and carboxylic acid to form ester and water

Esterification Reaction

REACTIONS OF ALCOHOL:

• The hydroxyl group (-OH) of the carboxylic acid and Hydrogen from the alcohol combined to form water

• The remaining parts forms an ester bond, connecting the alcohol and the acid

Esterification Reaction

REACTIONS OF ALCOHOL: In simple terms, it is a reaction where alcohol and an acid join together, losing water and forming esters.

Halogenation Reaction

REACTIONS OF ALCOHOL:

• In the given (specific substitution reaction), an alcohol (-OH) is replaced by a halogen molecule. Then the (-OH) forms water)

• The hydrochloride protonates the (-OH) converting it into a better leaving group which is the water (nawawala).

• The chloride ion from the hydrochloride attacks the carbon replacing the (-OH).

Substitution Reaction

REACTIONS OF ALCOHOL: a reaction where one atom or a group in a molecule is replaced by another molecule.

Oxidation Reaction, Dehydration Reaction, and Halogenation Reaction

REACTIONS OF ALCOHOL

Acid-Base Reaction

REACTIONS OF PHENOLS: It is a reaction where an acid donates a proton or Hydrogen ion to a base.

Acid-Base Reaction

REACTIONS OF PHENOLS:

Slightly Acidic

REACTIONS OF PHENOLS: Phenol is ________ due to the resonance stabilization of the phenoxide ion.

Phenoxide Ion

REACTIONS OF PHENOLS:Phenol is slightly acidic due to the resonance stabilization of the?

Weak Acids

REACTIONS OF PHENOLS: PHENOLS AND THIOLS ARE _______ AND CAN REACT WITH BASES TO FORM SALTS

Losing

REACTIONS OF PHENOLS: Phenol reacts with bases like NaOH by _____ a proton to form a phenoxide ion

Electrophilic Substitution Reaction

REACTIONS OF PHENOLS: This is a reaction when an electrophile replaces a hydrogen in an aromatic ring

Bromination

REACTIONS OF PHENOLS: This reaction is also called as?

Electrophilic Substitution Reaction

REACTIONS OF PHENOLS:

• The (-OH) group activates the benzene ring, making it highly reactive at the ortho and para positions.

• Bromide adds (replaces the Hydrogen) to these positions by?

Ortho, and Para Positions

ELECTROPHILIC SUBSTITUTION OF PHENOLS: The (-OH) group activates the benzene ring, making it highly reactive at what positions?

Acid-Base Reaction, and Electrophilic Substitution Reaction

REACTIONS OF PHENOLS

Oxidation to Disulfides

REACTIONS OF THIOLS: A reaction where thioethers (R-S-R) are oxidized to sulfoxides, or sulfones

Sulfoxides, or Sulfones

REACTIONS OF THIOLS: Oxidation to Disulfides is a reaction where thioethers (R-S-R) are oxidized to?

Disulfide Bonds

REACTIONS OF THIOLS: Thiols are oxidized by losing hydrogen to form a sulfur atom. This forms _________, which are common in proteins.

Proteins

OXIDATION TO DISULFIDES OF THIOLS: This forms disulfide bonds, which are common in?

Oxidation to Disulfides

REACTIONS OF THIOLS: SH can be oxidized to thioethers which can be further oxidized to sulfoxides and sulfones.

Thioethers

OXIDATION TO DISULFIDES OF THIOLS: SH can be oxidized to __________ which can be further oxidized to sulfoxides and sulfones.

Oxidation to Disulfides

REACTIONS OF THIOLS: Thiols loses hydrogen to form a sulfur atom during oxidation, as a result two thiol molecules can linked together to form a disulfide bonds

Sulfhydryl Group

REACTION WITH METALS OF THIOLS: Thiols are organosulfur compounds that contain _________

Strong Affinity

REACTION WITH METALS OF THIOLS: They are known for their higher reactivity especially with metals → The reaction of thiols with metals is primary due to the _________ between sulfur and metal ions

Reaction with Metals

REACTIONS OF THIOLS:

Acidic

REACTION WITH METALS OF THIOLS: Thiols are _____ and react with heavy metals ions (Mercury)

Reaction with Metals

REACTIONS OF THIOLS: Sulfur attaches to mercury/metal forming metal sulfide complexes (stable complexes)

Metal Sulfide Complexes

REACTION WITH METALS OF THIOLS: Sulfur attaches to mercury/metal forming? (stable complexes)

Oxidation to Disulfides, and Reaction with Metals

REACTIONS OF THIOLS

Acidic Cleavage Reaction

REACTIONS OF ETHERS: It is a reaction where a bond is broken, splitting of molecule into two parts

Acidic Cleavage by Hydrogen Iodide or Hydrogen Bromide

REACTIONS OF ETHERS: First Carbon (R1) in ether is attack by iodine, then the second carbon (R2) forms alcohol (ethanol)

Acidic Cleavage by Hydrogen Iodide or Hydrogen Bromide

REACTIONS OF ETHERS:

• Hydroiodic acid (HI) protenates the ether, making the oxygen a better leaving group

• Hydroiodic acid (HI) donates proton (H+) to another molecule

• The iodide ion attacks, breaking the Carbon-Oxygen bond, the ether is protonated making it susceptible to nucleophilic attack

• First Carbon (R1) in ether is attack by iodine, then the second carbon (R2) forms alcohol (ethanol)

Autooxidation to Peroxides

REACTIONS OF ETHERS: it is a slow oxidation reaction of organic compounds with oxygen from the air.

Slow Oxidation

AUTOOXIDATION TO PEROXIDES: It is a ______________ reaction of organic compounds with oxygen from the air.

Peroxides

AUTOOXIDATION TO PEROXIDES: Ethers react with oxygen in the air to form ________, which are unstable and explosive

Autooxidation to Peroxides

REACTIONS OF ETHERS:

Acidic Cleavage by Hydrogen Iodide or Hydrogen Bromide, and Autooxidation to Peroxides

REACTIONS OF ETHERS

Oxidation to Sulfoxides and Sulfones

REACTION OF THIOETHERS: sulfur undergoes oxidation, forming first sulfoxides (SO) then sulfones (SO2).

Oxidation to Sulfoxides and Sulfones

REACTION OF THIOETHERS:

Sulfoxides

REACTION OF THIOETHERS: What is R-SO-R

Sulfones

REACTION OF THIOETHERS: What is R-SO2-R

Methylation Reaction

REACTION OF THIOETHERS: this is a reaction where a methyl group (CH3) is added to the molecule.

Methylation Reaction

REACTION OF THIOETHERS:

• Sulfur donates electrons to the alkyl halide (iodomethyl), forming a sulfonium salt.

• The sulfur atom in the thioether reacts with iodomethyl, adding a methyl group to the sulfur, and forming a sulfonium salt.

Sulfonium Salt

METHYLATION OF THIOETHERS: The sulfur atom in the thioether reacts with iodomethyl, adding a methyl group to the sulfur, and forming a __________

Oxidation to Sulfoxides and Sulfones, and Methylation

REACTION OF THIOETHERS