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 ALKANES

• CHEMICAL PROPERTIES:
1. Halogenation: addition of a halogen
2. Combustion: blue flame

• IMPORTANT COMPOUNDS:
1. METHANE: simplest alkane, marsh gas, main constituent of natural gas
2. PROPANE: fuel sold as “bottled gas”

 ALKENES
• CHEMICAL PROPERTIES:
1. Substitution reactions
a. Addition of H2 (hydrogenation)
b. Halogenation (production of alkyl halides)
➢ Test for unsaturation
➢ Deep red color disappears when a double or triple bond is present
a. Addition of hydrogen halide (HX)
➢ Markonikov’s rule: addition of HX, the hydrogen goes to the carbon that already has more hydrogen atoms
a. Addition of water/Hydration
➢ Catalyst is needed (usually sulfuric acid) because without it, water does not react with alkenes; follows Markonikov’s rule.
1. Combustion: luminous flame
2. Polymerization: formation of long chains (Ex: rubber, nylon plastic)

• IMPORTANT COMPOUNDS:
1. TERPENES: Examples, essential oils (gives plants their pleasant odors), Vitamin A, Beta-carotene (2 vitamin A units)
2. PHEROMONES: used by insects to transmit messages to each other
3. ETHYLENE: application of ethylene gas in warehouses produces controlled ripening of fruits and vegetables

 ALKYNE COMPOUNDS
➢ Chemical properties similar with alkenes
➢ ETHYNE: simplest and most important; common name is acetylene and the high temperature of acetylene flame is used for
torches that can cut and weld steel

 AROMATIC HYDROCARBONS
• IMPORTANT COMPOUNDS:
1. BENZENE: simplest and most important (discovered by Michael Faraday)
• Toxic material
• Liquid form: poisonous if ingested; vapor form: absorbed by breathing or through the skin
• Long-term inhalation: liver damage, cancer
• Derivatives: toluene, phenol, aniline, benzoic acid
1. FUSED AROMATIC RINGS: solid at room temperature and undergo aromatic substitutions
• Naphthalene (2 rings), anthracene (3 rings), phenanthrene (4 rings)

 ALCOHOLS
• CHEMICAL PROPERTIES:
1. Neutral, neither acidic nor basic
2. Reaction with hydrogen halides
• Reactivity: 3°>2°>1°
1. Dehydration to give an alkene
• Zaitsey’s rule: when two products are possible, the major product is the one in which the H-atom is lost from the carbon atom
that had fewer H-atoms.
1. Oxidation
• 1° ROHRCHO (aldehyde)RCOOH (carboxylic acid)
• 2° ROH RCOR' (ketone)
• 3° ROHno reaction
• IMPORTANT COMPOUNDS:
1. METHANOL
➢ Sometimes known as wood alcohol because it was made from destructive distillation of wood
➢ Solvent for paints, shellacs and varnishes; used to make formaldehyde; good denaturant for ethyl alcohol due to taste and
poisonous properties.
1. ETHANOL (a.k.a grain alcohol)
➢ Present in alcoholic beverages through fermentation of grains, fruits or vegetables
➢ 70% solution: antiseptic
1. ETHYLENE GLYCOL (1,2-ethanediol): Antifreeze for automobile radiators; refrigerants
2. ISOPROPYL ALCOHOL (a.k.a. rubbing alcohol)
➢ Lowers fever due to cooling sensation on the skin; astringent
➢ Intermediate in the production of acetone
1. GLYCEROL
➢ Sweet, nontoxic, infinitely soluble in water.
➢ Main ingredient in suppositories; sweetening agent; solvent for medicines; lubricant in medical laboratories; manufacture of
nitroglycerine
1. PHENOL: Aqueous solution: carbolic acid
➢ Anti-oxidant; disinfectant for surgical instruments and utensils
1. MENTHOL: Pleasant, minty odor and is used in shaving creams, cigarettes and toothpastes
2. CRESOL: Saponated cresol (a.k.a. LYSOL): disinfectant which is better and less toxic than phenol

 ETHERS
• CLASSIFICATIONS:
1. Open chain
a. Symmetrical: R groups are the same
b. Mixed/unsymmetrical: R groups are different
2. Cyclic
a. Epoxides, oxiranes, oxacyclopropane: ether is part of a 3-membered ring
b. Cyclic with more than 3 members
✔ Just like alkanes, they are inert and unreactive towards most reagents
✔ DIETHYL ETHER
○ Formerly the most important general anesthetic (reversible with oxygen)
○ On standing for periods of time, oxidized by air to give high boiling explosive compounds called PEROXIDES

 THIOLS (a.k.a. mercaptans)


➢ Sulfur analogs of the corresponding alcohols, phenols and ethers
➢ PROPERTIES: Foul odor, weak acids (somewhat weaker than phenols); easily oxidizable to disulfides

 ALDEHYDES AND KETONES


• PHYSICAL PROPERTIES
➢ Lower boiling points than alcohols
➢ Polar molecules
➢ Form hydrogen bonds with water
➢ Have strong odors

• CHEMICAL PROPERTIES:
1. Oxidation:
➢ Aldehydes are easy to oxidize, ketones are not.
a. Tollen’s test: for both aliphatic and aromatic aldehydes
b. Benedict’s test: aliphatic aldehydes only
c. Iodoform test: Test for methyl ketones
1. Addition of H2 (reduction to alcohols)
2. Addition of alcohols (acetal formation)
3. Addition of Grignard reagents (RMgX)
a. 1 carbon aldehyde1° ROH
b. More than 1 carbon aldehyde 2° ROH
c. Ketones 3° ROH

• IMPORTANT COMPOUNDS
1. ACETALDEHYDE
➢ Often converted to cyclic trimer (PARALDEHYDE) due to low boiling point
➢ Intermediate in the manufacture of acetic acid, ethyl acetate, vinyl acetate which in turn are used in the production of synthetic
rubber and water based paints
1. FORMALDEHYDE
➢ 37% aqueous solution: FORMALIN (preservative for anatomical specimens)
➢ Disinfectant in hospitals
1. BENZALDEHYDE (“bitter oil of almond”): Flavoring agent
2. CHORAL
➢ Choral hydrate (“knock-out drops”): sleeping tablet
➢ Starting material for insecticide (DDT)
1. CINNAMALDEHYDE
➢ Chief ingredient of oil of cinnamon bark; cinnamon flavoring agent
1. ACETONE: Solvent for paints, lacquers,and cellulose acetate due to miscibility with both water and non-polar solvent
2. VANILLIN: Fragrant component of vanilla beans; flavoring agent
3. CITRAL
➢ Major component of lemon grass oil
➢ Intermediate in vitamin A manufacture
1. MUSCONE
➢ From musk deer; odorous component of musk (perfumery); sex attractant
➢ Present in expensive perfumes as fixative
1. ACETOPHENONE: Formerly used as hypnotic
2. CHLOROACETOPHENONE: Lacrimator and used as a tear gas

 CARBOXYLIC ACIDS

• PHYSICAL PROPERTIES

1. Physical state
➢ C1-C3: colorless liquids with pungent smell.
➢ C4-C9: oily liquids with an odor of rancid butter
➢ >C9: colorless, odorless, waxy solids
1. Boiling points
➢ Higher boiling point than aldehydes and ketones and even alcohols of comparable masses due to more extensive association of
carboxylic acid molecules through intermolecular hydrogen bonding.
1. Solubility
➢ C1-C4: miscible with water; decreases with increasing number of carbon atoms
➢ Soluble in less polar organic solvents like benzene, ether, alcohol etc

• CHEMICAL PROPERTIES:
1. Salt formation
2. Conversion into functional derivatives (see diagram above)
3. Reduction to alcohols

• IMPORTANT COMPUNDS
1. ACETIC ACID: 15% in vinegar
2. OXALIC ACID: Simplest dicarboxylic acid, present in leafy vegetales including spinach and rhubarb
3. TRICHLOROACETIC ACID: 50% aqueous solution: used to cauterize gums
4. SALICYLIC ACID: Treatment of fungal infections and removal of warts and corns
5. CITRIC ACID
➢ Found in citrus fruits; used as flavoring and preservative of food and beverages.
➢ Used in ice cream to keep fat globules separated
1. BENZOIC ACID
➢ Antifungal agent
➢ Sodium salt: sodium benzoate (food preservative)
1. ACETYLSALICYLIC ACID (aspirin): Analgesic, antipyretic, anti-inflammatory
2. ACETAMINOPHEN (paracetamol): Substitute for aspirin, also reduces fever but not swelling

 ESTERS
➢ Reaction between carboxylic acid and alcohol
➢ Low boiling points
➢ Same with solubility of carboxylic acids
➢ Odor is generally very pleasant.
➢ Undergo hydrolysis reactions

 AMIDES
➢ Reaction between carboxylic acid and amine
➢ Undergo hydrolysis reactions

• IMPORTANT COMPOUNDS
1. ACETANILIDE: antipyretic and analgesic
2. NIACINAMIDE (Vitamin B3): prophylaxis and treatment of pellagra (disease characterized by skin changes and nerve dysfunctions)
3. NICOTINAMIDE: prevents pellagra: Together with nicotinic acid (niacin)=makes NAD for the body
4. SULFANILAMIDE: Therapeutic effects against pneumonia, diarrhea and streptococcal infections

 AMINES
➢ Derived from ammonia by replacing 1,2 or 3 H’s with alkyl or aryl groups
➢ Basicity (salt formation)
○ Amine (proton acceptor/base) + acid  amine salts
• CLASSIFICATION:
1. Based on the number of H-atoms replaced by alkyl or aryl groups
a. PRIMARY AMINES (RNH2): one H replaced by R
b. SECONDARY AMINES (R2NH): two H-atoms replaced by R
c. TERTIARY AMINES (R3N): all three H-atoms replaced by R
2. Based on the group attached to Nitrogen
a. ALIPHATIC AMINES: alkyl group attached to N
b. AROMATIC AMINES: aryl group attached to N

• IMPORTANT COMPOUNDS
1. ANILINE: Active ingredient in tobacco; preparation of drugs and dyes
2. CAFFEINE: Responsible in stimulating action of coffee and tea; also present in colas, cocoa, and “stay awake pills”
3. MORPHINE: Most effective pain-killer known; addictive
4. CHOLINE: Found in egg yolks, meat and fish; essential for growth
5. AMPHETAMINE
➢ Synthetic amine which is a powerful stimulant of the CNS
➢ Used to counter mild depression, reduce hyperactivity in children (ADHD) and as appetite depressant for people trying to lose
weight (BANGKOK PILLS)
1. BARBITURIC ACID: Drug of choice for status epilepticus

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