SCH4U Organic Chemistry. hydrocarbon derivatives. mitchell kember

Transcription

1 SCH4U rganic Chemistry hydrocarbon derivatives mitchell kember

2 (Family Name) Note: penta can be replaced by meth/eth/prop/but/ # stands for a number from the chain (IUPAC name) (General Formula) (IUPAC name) (structural diagram) (structural diagram) (Something about polarity) Note: Polar higher boiling point & more soluble in water Reaction Type: (preparation reaction) Reaction Type: (reaction)

3 rganic Halides RX Just like alkyl groups (F fluoro, Cl chloro, Br bromo, I idodo). trichloromethane H ClCCl Cl 1,2-difluorocyclohexane More polar than HCs due to halogen electronegativity. Halogenation: alkene/alkyne + halogen alkyl halide Elimination: alkyl halide + H alkene + H2 + halide ion Amine synthesis: alkyl halide + NH3 amine + halide F F

4 Alcohols RH #-pentanol or #,#-pentanediol, # is location of H (polyalcohol) (hydroxyl group) ethanol CH3CH2H 1-propanol CH3CH2CH2H degree 1º CH2H 2º CHH 3º CH Much more polar than HCs and forms hydrogen bonds due to hydroxyl group. Dissolves polar & nonpolar compounds. Elimination: alcohol alkene + H2 xidation: alcohol + ()* aldehyde/ketone + H2 Condensation: alcohol + alcohol ether + H2

5 Ethers ethoxypentane or methyl ethyl ether or dipentyl ether (smallest first) (non-systematic) (R and R are same) methoxymethane (dimethyl ether) CH3CH3 methoxyethane (methyl ethyl ether) CH3CH2CH3 More polar than HCs but less than alcohols. No hydrogen bonding. Mixes readily with polar & nonpolar substances. Condensation: see alcohols RR

6 Aldehydes pentanal (prefix includes R and C) methanal HCH butanal CH3CH2CH2CH RCH More polar than HCs due to carbonyl =C=, but less polar than alcohols. No hydrogen bonding. xidation: see primary (1º) alcohols xidation: aldehyde + ()* carboxylic acid Hydrogenation: aldehyde + hydrogen 1º alcohol

7 Ketones #-pentanone (prefix includes R, C, and R ) propanone CH3CCH3 3-pentanone CH3CH2CCH2CH3 RCR Same as aldehydes. xidation: see secondary (2º) alcohols Hydrogenation: ketone + hydrogen 2º alcohol

8 Carboxylic Acids pentanoic acid (prefix includes R and C) or pentanedioic acid (carboxyl at both ends) methanoic acid ethanoic acid (acetic acid) HCH CH3CH RCH Polarity and hydrogen bonding similar to alcohols due to the carboxyl group CH (carbonyl + hydroxyl). xidation: see aldehydes Condensation: carboxylic acid + alcohol ester + H2 Condensation: carboxylic acid + amine amide + H2

9 Esters pentyl pentanoate R R and C methyl methanoate HCCH3 1-methylpropyl ethanoate CH3 RCR CH3CCH2CH2CH3 Less polar than carboxylic acids. No hydrogen bonding. Condensation: see carboxylic acids Hydrolosis: ester + H2 carboxylic acid + alcohol

10 Amines Just like alkyl groups (NH2 amino), N as # or pentylamine (non-systematic) RNR R aminomethane (methylamine) CH3 HNH N,N-dimethylaminoethane CH3 CH3CH2NCH3 degree 1º NH2 2º NH 3º N More polar than HCs due to NC and NH bonds, but less polar than alcohols. ften has an unpleasant odour. Condensation: 1º amine + alkyl halide 2º amine + halide

11 Amides N-butyl-N-pentyl pentanamide R R R and C ethanamide CH3CNH2 RCNR N,N-dimethyl propanamide CH3 CH3CH2CNCH3 R Weak bases, generally insoluble in water. Amides with two NH bonds are more polar. Condensation: see carboxylic acids Hydrolosis: amide + H2 carboxylic acid + amine

12 Reaction Classification Addition Hydrogenation Halogenation Hydrohalogenation Hydration Hydrolosis Saponification Elimination Dehydration Condensation Esterification Substitution xidation Combustion See the flowchart on page 83 of the textbook. Good luck on the test on Tuesday, 10 December 2013.