Summary Sheet - Introduction to Chemical Reactivity, Nomenclature, Boiling Points, and Water Solubility http://masterorganicchemistry.

com

Reactant #1 Reactant #2 Product Example Notes The Four Types of Intermolecular Bonding in Organic Chemistry •Boiling point increases with strength of the
intermolecular interactions.
H H Pd/C, H2 HH HH •Water solubility increases with polarity.
Alkene Pd/C + H2 Alkane cis addition (hydrogens go Type of
R R R R on same side of alkene) Name Interaction Found in Example Strength Notes

HCl gives rise to greatest water

Amine Acid Ammonium amines but NOT amides Ionic Attraction Salts NH4 Cl Strongest
R NH2 R NH3Cl between solubility (most polar)
salt (amides are not basic on nitrogen)
point charges δ+ also highest boiling points
O O O
EtNH2 H H
Carboxylic Base Salt
acid (Carboxylate Ph OH Ph O EtNH3 δ−
salt) Attraction between Water, alcohols O
positively charged H carboxylic acids H H 2nd strongest 2nd greatest for effect on
Hydrogen
O O and negatively charged amides, amines water solubility and boiling
MeOH Bonding
O, N or F. points
Carboxylic Alcohol, Ester R OH R OMe Alcohols used as solvent δ−
acid acid, heat H2SO4, Δ O
δ+
ketones, aldehydes,
Attraction between esters, alkyl halides, O δ− Increases as electronegativity
O H2O O This is the reverse of the Dipole- 2nd weakest difference increases
Ester Water, Carboxylic dipole moments etc. - any molecule
above reaction. Dipole
acid, heat acid caused by differences with a strongly δ+ 3rd greatest for effect on water
R OMe H2SO4, Δ R OH in electronegativity electronegative solubilty and boiling points
Here we use water as solvent. element (O, N, F, Cl, Br)
Increases with surface area
(increasing length of carbon
O H2O O Attraction between Hydrocarbons Name Weakest chains)
Ester Water, Carboxylic This is called ester hydrolysis Van Der Waals
base acid or saponification (London forces) temporary dipoles worst for water solubility
R OMe NaOH R OH
(least polar)
best for solubility in non-polar
solvents (e.g. pentane)

R R OH alcohol forms on most

substituted carbon Functional Group Name Example Name
HCl # Carbons Root
Alkene Water, acid Alcohol H (Markovnikoff rule)
R CH2 H2O R C 1 Meth- R– Alkyl Pentane
H2 proceeds through carbocation
2 Eth- –OH Hydroxyl OH Pentanol or pentyl alcohol
R R Cl halide adds to most
HCl substituted carbon 3 Prop-
Alkene Strong acid Alkyl H (Markovnikoff rule) –Cl, –Br, –F, –I Halide Cl Pentyl chloride
R CH2 R C 4 But-
halide H2 proceeds through carbocation
5 Pent- –NH2 Amine NH2 Pentylamine

6 Hex- O Ether O Pentyl methyl ether

Br R R R
Br2 H Results in trans product
Alkene Br2 Dibromide R H 7 Hept-
R R Br –SH Thiol SH Pentane thiol
8 Oct-
R
K2CrO7 C C Alkene Pentene
Alcohol K2CrO7 Carboxylic acid OH O 9 Non-
(primary alcohol) R R
H2O O O
OR ketone OH 10- Dec-
(secondary alcohol) Aldehyde Pentanal
R C H H
R
K2CrO7 O O
OH O Note that secondary alcohols
R R stop at the ketone stage Ketone Butyl methyl ketone
H2O Primary carbon: attached to ONE R C R Me OR 2-pentanone
R R carbon atom
O O
R Secondary: attached to TWO Carboxylic Pentanoic acid
KMnO4 carbon atoms R C OH acid OH
Alcohol KMnO4 Carboxylic acid OH O
(primary alcohol) R R
H2O Tertiary: attached to THREE O O
OH carbon atoms
R C OR Ester OMe Methyl pentanoate
Cl2, hγ Cl Cl Free-radical reaction Quaternary: attached to FOUR
Alkyl chloride O O
Alkane Cl2, hν R Me R CCl3 (number of new C–Cl carbon atoms
Amide N-methyl pentamide
(or peroxides) bonds depends on R C NH2 NHMe
# of equivalents)
Other important nomenclature terms to remember
R R
Br2, FeBr3 Also gives 1,4 (para) product Copyright 2012
Br Br James A.Ashenhurst
Br2, FeCl3 but never 1,3 (meta) product OH R R R
Benzene Aryl bromide Aug 2012, version 1.1
derivative james@masterorganicchemistry
R .com
Phenyl isopropyl
[ox] Trans Cis
R-SH RS–SR (e.g. phenyl e.g. isopropanol 1,2 1,3
Thiol "Oxidant" Disulfide bromide) 1,4
ortho meta
para