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Reactant #1 Alkene Reactant #2 Pd/C + H2 Product Alkane H R Amine Acid Ammonium salt H R HCl R NH2 O Carboxylic acid Base Salt (Carboxylate Ph salt) O Carboxylic acid Alcohol, acid, heat Ester R OH OH MeOH H2SO4, R EtNH2 Ph R O O EtNH3 O OMe Alcohols used as solvent Hydrogen Bonding Attraction between positively charged H and negatively charged O, N or F. Water, alcohols carboxylic acids amides, amines NH3Cl Example Pd/C, H2 HH HH R R Notes cis addition (hydrogens go on same side of alkene) amines but NOT amides (amides are not basic on nitrogen) The Four Types of Intermolecular Bonding in Organic Chemistry Type of Interaction Attraction between point charges
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Boiling point increases with strength of the intermolecular interactions. Water solubility increases with polarity. Strength Strongest Notes gives rise to greatest water solubility (most polar) also highest boiling points
Name
Found in Salts
Example NH4 Cl + H O H
Ionic
O H H + O +
2nd strongest
O Attraction between dipole moments caused by differences in electronegativity ketones, aldehydes, esters, alkyl halides, etc. - any molecule with a strongly electronegative element (O, N, F, Cl, Br)
Ester
Carboxylic acid
O R OMe
H2O H2SO4, R
O OH
This is the reverse of the above reaction. Here we use water as solvent.
DipoleDipole
2nd weakest
Increases as electronegativity difference increases 3rd greatest for effect on water solubilty and boiling points Increases with surface area (increasing length of carbon chains) worst for water solubility (least polar) best for solubility in non-polar solvents (e.g. pentane)
Ester
Water, base
Carboxylic acid
O R OMe
H2O NaOH R
O OH
Hydrocarbons
Name
Weakest
HCl H2O R
R OH C H2 R Cl R C H2 H H
alcohol forms on most substituted carbon (Markovnikoff rule) proceeds through carbocation halide adds to most substituted carbon (Markovnikoff rule) proceeds through carbocation
# Carbons 1 2
Root MethEthPropButPentHexHept-
Example
Name Pentane OH Cl NH2 O SH Pentanol or pentyl alcohol Pentyl chloride Pentylamine Pentyl methyl ether
HCl
3 4 5
Alkene
Br2
Dibromide
Br2
Br H R
6 H Results in trans product 7 8 O OH 9 10Note that secondary alcohols stop at the ketone stage
Br R R
SH OctNonDecC O R C H O R C R O R C OH O R C OR O R C NH2 Other important nomenclature terms to remember Br Also gives 1,4 (para) product but never 1,3 (meta) product Phenyl Br OH isopropyl e.g. isopropanol R Trans Cis R R R C
Pentane thiol Pentene Pentanal Butyl methyl ketone OR 2-pentanone Pentanoic acid
Alcohol
K2CrO7
OH
K2CrO7 H2O
OH
K2CrO7 H2O R
R O R R R Cl R O OH Cl CCl3 Free-radical reaction (number of new CCl bonds depends on # of equivalents) Primary carbon: attached to ONE carbon atom Secondary: attached to TWO carbon atoms Tertiary: attached to THREE carbon atoms Quaternary: attached to FOUR carbon atoms
Alcohol
KMnO4
OH
Alkane
Alkyl chloride
Me
Br2, FeBr3
Copyright 2012 James A.Ashenhurst Aug 2012, version 1.1 james@masterorganicchemistry .com 1,2 ortho 1,3 meta 1,4 para