bills

revised organic chemistry today with jia en, beejuan and siuchu!

alkanes

1. free radical substitution mechanism: initiation, propagation, termination
2. optical isomerism

alkenes

1. production by dehydration of primary/secondary alcohols
2. electrophilic addition with hydrogen halides (in aqueous medium and inert solvent)
3. markovnikov's rule
4. zaitsev's rule
5. oxidative cleavage with hot acidified potassium permanganate
6. formation of diol with cold alkaline potassium permanganate
7. formation of alcohol with cold concentrated sulphuric acid, followed by warm water
8. geometric isomerism

arenes

1. electrophilic substitution mechanism: generation of electrophile, electrophilic attack, loss of proton
2. halogen carriers
3. activating or deactivating groups
4. 2,4- or 3,5- directing groups
5. methylbenzene: nitration
6. oxidation of alkylbenzene to benzoic acid

halogenoalkanes

1. production from alcohols by phosphorous penta-/trichloride or thionyl chloride in pyridine
2. nucleophilic substitution mechanisms 1 and 2
3. nucleophilic substitution with hydroxide ions (in aqueous medium) to form alcohols
5. nucleophilic substitution with ammonia in ethanol (heated in sealed tube) to form amines/polyalklyamines/polyalkylammonium salts
6. nucleophilic substitution with cyanide ions to form nitriles
7. nucleophilic substitution with alkoxide ions to form alkoxy compounds (williamson synthesis)
8. dehydrohalogenation using hydroxide in alcoholic medium to form alkenes

halogenoarenes

1. partial double bond character
2. 2,4-directing halogen atoms

hydroxy compounds

1. formation of halogenoalkanes using phosphorous penta-/trichloride or thionyl chloride in pyridine
2. oxidation to aldehydes, ketones and carboxylic acids
3. iodoform test for methyl alcohols
4. acidity comparison with alcohol, water and phenol
5. electrophilic susbtitution reactions of phenol with bromine (aqueous medium or inert solvent), and nitric acid (concentrated or dilute)
6. test for phenol using neutral iron(III) chloride

carbonyl compounds

1. reduction to form alcohols
2. oxidation of aldehydes to carboxylic acids
3. 2,4-dinitrophenylhydrazine test for carbonyl compounds
3. iodoform test for methyl carbonyl compounds
4. fehling's test for aliphatic aldehydes
5. tollens' test for aromatic aldehydes
6. nucleophilic addition with hydrogen cyanide to form cyanohydrins

carboxylic acids

1. reduction to form alcohols
2. stability of carboxylate anion
3. sodium carbonate test for carboxylic acids

carboxylic acid derivatives

1. acyl chloride formation from carboxylic acids using phosphorous penta-/trichloride or thionyl chloride in pyridine
2. immediate hydrolysis of acyl chlorides on contact with water
3. ester formation from acyl chlorides and alcohols
4. hydrolysis of esters in acidic or alkaline medium
5. amide formation from acyl chlorides and amines
6. reduction of amides to form amines
7. hydrolysis of amides in acidic or alkaline medium

amines

1. basicity
2. litmus test for amines
3. formation from reduction of amides
4. formation from reduction of nitriles
5. reaction with acyl chlorides to form amides

amides

1. stereochemistry of amides due to hybridisation of nitrogen
2. reduction of amides to amines
3. formation from acyl chlorides and amines

amino acids

1. zwitterion formation
2. pH-buffering properties
3. solubility in aqueous/acidic/alkaline affected by zwitterion state
4. r-group interactions: hydrogen bonding, hydrophobic interactions, ionic interactions, disulphide bridges

proteins

1. primary structure: sequence of amino acids
2. secondary structure: local conformation of polypeptide chain
3. alpha-helix
4. anti-/parallel beta-pleated sheet
5. hydrogen bonding between amide bonds
6. tertiary structure: overall conformation of polypeptide chain
7. hydrophobic interactions
8. ionic interactions
9. disulphide bridges
10. quarternary structure: interactions of polypeptide chains to form globular protein
11. enzymes

oh yes i'm so going to keep my A for chemistry! i swept the floor at night.