org chem

• Alcohols


  1. OH (Hydroxyl)
• Alcohols


  • Organic analogues of water
• Water solubility of alcohols

  Decreases as the number of carbons increases
• Boiling point of alcohols

  Increases as the number of carbons increases
• Preparation of alcohols

  1. Hydration of alkenes (addition of water)

  2. Catalytic hydrogenation or metal halide reduction of aldehydes, ketones, carboxylic acids

  3. Nucleophilic addition of organometallic reagents to aldehydes, ketones, alkyl halides, and esters
• Dehydration of alcohols

  1. Removal of water

  2. Product: Alkenes
• Oxidation of alcohols

  1. Reagent: Potassium dichromate (K2Cr2O7)

  2. Primary alcohol --> aldehyde --> carboxylic acid

  3. Secondary alcohol --> ketone

  4. Tertiary alcohol (no reaction)
• Lucas test


  • Reagent: Zinc chloride in concentrated HCl differentiates alcohols by forming an insoluble layer
  • Tertiary alcohols are the most reactive
  • Primary alcohols need heat
• Williamson's reagent


  • For synthesis of ethers
  • Most reactive: Methanol > Primary > Secondary > Tertiary
• Pharmaceutically important alcohols

  • Methanol (CH3OH)
  • Ethanol
  • Isopropyl alcohol
  • Ethylene glycol
• Methanol


  • Formerly obtained from destructive distillation
  • Used to produce formaldehyde (starting material for plastics)
  • Toxicity: Methanol ---> Formaldehyde --> Formic acid (blindness due to metabolic acidosis)
  • Antidote: Ethanol
• Ethanol


  • Present in alcoholic beverages
  • Obtained from fermentation of sugars and starch
  • Antiseptic (70% solution)
  • Used as solvent in tinctures and other alcoholic medicinal preparations
  • Ethanol metabolism occurs in the liver: EtOH ---> Acetaldehyde --> Acetic acid (causes liver damage)
• Isopropyl alcohol


  • Used in the production of acetone
  • Pharmaceutical solvent
• Ethylene glycol


  • Antifreeze
  • Brake fluids
  • Ink, paints
  • Pharmaceutical solvent
  • Ethylene glycol --> Oxalate (Oxalic acid) + Calcium --> (hypocalcemia)
  • Calcium oxalate deposits - cause kidney stones
• Phenols


  • Hydroxyl group attached to an aromatic hydrocarbon group
  • More acidic than alcohol
• Phenols

  • Have higher boiling points
  • Susceptible to oxidation
• Preparation of phenols

  1. Hydrolysis of diazonium salts

  2. Alkali fusion of sulfonates
• Reactions of phenols

  • Electrophilic substitution
  • Salt formation with alkali
  • Ether formation
  • Esterification
  • Carbonation (Treatment with CO2)
  • Reimer-Tiemann reaction
  • Reaction with formaldehyde
• Pharmaceutically important phenols

  • Phenol (Carbolic acid)
  • Cresol
  • Lysol
• Phenol (Carbolic acid)


  • Disinfectant for surgical instruments
  • Antiseptic for skin
  • Starting material in the manufacture of aspirin, detergents, dyes, herbicides, explosives
  • Bacteriostatic: 0.1%-1%
  • Bactericidal/Fungicidal: 1%-2%
  • Irritating and corrosive to tissues: 5%
• Cresol and Lysol


  • Colorless, but turns dark brown upon prolonged exposure to light and air
  • Commonly used as a surface disinfectant
  • Less toxic than phenol
• Glycerol


  • Odorless, sweet liquid
  • Used in the manufacture of certain plastics
  • Solvent in liquid medications
  • Ingredient in cosmetics formulation
  • Vehicle for suppositories
  • When ingested, it attracts water into the intestines and softens the stool, relieving constipation
• Cholesterol


  • Waxy, fat-like substance found in the cell membrane
  • Precursor for the synthesis of reproductive hormones and bile acids
• Hexyl resorcinol


  • Antiseptic and germicide
  • Commonly used in mouthwash
• Menthol


  • From Peppermint oil
  • White, crystalline substance
• Geraniol


  • From Rose oil
  • Commonly used in food, fragrance, and cosmetic industry
• Glucose


  • Basic carbohydrate unit
  • Blood sugar
  • Found in fruits and honey
  • Major source of energy for cellular function
• Characteristics of an ideal antiseptic

  • Low surface tension
  • Non-irritating to tissue and non-allergenic
  • Must retain its activity in the presence of body fluids
  • Has rapid and sustained action against microorganisms
• Ethers


  • R-O-R
  • Organic relatives of water, where alkyl groups replace both hydrogen atoms
  • Two hydrocarbons bonded to an oxygen atom
  • Commonly used as solvents in organic reactions
• Preparation of ethers

  1. Williamson ether synthesis

  2. Acid-catalyzed addition of alcohols to alkenes

  3. Oxidation of ethylene
• Ethers


  • Simple ethers are unreactive towards bases, oxidizing agents, and reducing agent
  • Nucleophilic substitution to yield alkyl halides
  • Nucleophilic substitution with acids and bases to yield alcohols
• Pharmaceutically important ethers

  • Anisole
  • Polyethylene glycol (PEG)
  • Ethylene oxide
  • Monobenzone
  • Eugenol
  • Naproxen
• Anisole


  Used in perfumes and cosmetics
• Polyethylene glycol (PEG)


  • Used in pharmaceuticals as surfactant, emulsifiers, humectant
  • Has a laxative effect
• Ethylene oxide


  • Gas sterilant
  • Fumigant for textiles and grains
• Monobenzone


  • Depigmenting agent in cases of excessive melanin production
  • Used in whitening preparations
• Eugenol


  • From Clove oil
  • Used to treat toothaches
  • Used in dentistry as temporary fillings when mixed with ZnO
• Naproxen


  • NSAID (Non steroidal anti-inflammatory drug)
  • For mild pain due to headaches, muscle aches, arthritis, menstrual pain, backaches, toothaches
• Thiols

  • R-SH
  • Sulfur analogs of alcohol
• Thiols


  • Lower boiling points than alcohols
  • Less polar than alcohols
  • More acidic than alcohols