Summary Sheet - Introduction to Chemical Reactivity, Nomenclature, Boiling Points, and Water Solubility
Reactant #1
Alkene
Amine
Carboxylic
acid
Reactant #2
Pd/C + H2
Product
Alkane
Acid
Ammonium
salt
Base
Example
H
H
R
R
R
R
NH2
Salt
(Carboxylate Ph
salt)
O
Ester
Ester
Alcohol,
acid, heat
Ester
Water,
acid, heat
Carboxylic
acid
Water,
base
Carboxylic
acid
OH
R
O
R
O
R
Water, acid
Alcohol
CH2
Alkene
Alcohol
Strong acid
Alkyl
halide
Br2
Dibromide
R
R
R
OH
OH
Carboxylic acid
(primary alcohol)
R
Alkane
Cl2, hν
(or peroxides)
R
Benzene
derivative
Br2, FeCl3
C
H2
C
H2
proceeds through carbocation
halide adds to most
substituted carbon
(Markovnikoff rule)
H
R
Br
H
R
proceeds through carbocation
Br
K2CrO7
OH
R
KMnO4
O
R
Cl
R
Br2, FeBr3
Cl
"Oxidant"
CCl3
R-SH
(number of new C–Cl
bonds depends on
# of equivalents)
Br
δ+
O δ−
2nd weakest
Increases as electronegativity
difference increases
3rd greatest for effect on water
solubilty and boiling points
δ+
Name
Weakest
Increases with surface area
(increasing length of carbon
chains)
Name
R–
Alkyl
2
Eth-
–OH
Hydroxyl
OH
Pentanol or pentyl alcohol
3
Prop-
4
But-
–Cl, –Br, –F, –I
Halide
Cl
Pentyl chloride
5
Pent-
–NH2
Amine
NH2
Pentylamine
6
Hex-
O
Ether
O
Pentyl methyl ether
7
HeptThiol
SH
Pentane thiol
8
Oct-
9
Non-
R
R
C
C
Example
Dec-
Alkene
Pentene
O
Aldehyde
R C H
O
R C R
O
Secondary: attached to TWO
carbon atoms
R C OH
H
Pentanal
O
Ketone
Me
Butyl methyl ketone
OR 2-pentanone
O
Carboxylic
acid
Pentanoic acid
OH
O
O
R C OR
Quaternary: attached to FOUR
carbon atoms
Name
Pentane
O
Primary carbon: attached to ONE
carbon atom
Ester
OMe
Methyl pentanoate
O
O
Amide
R C NH2
Also gives 1,4 (para) product
but never 1,3 (meta) product
Br
Phenyl
RS–SR
2nd greatest for effect on
water solubility and boiling
points
N-methyl pentamide
NHMe
Other important nomenclature terms to remember
R
Aryl bromide
Disulfide
Free-radical reaction
2nd strongest
δ−
Functional Group
Root
Tertiary: attached to THREE
carbon atoms
OH
[ox]
Thiol
Note that secondary alcohols
stop at the ketone stage
R
H
Meth-
10-
O
R
O
gives rise to greatest water
solubility (most polar)
also highest boiling points
1
# Carbons
R
K2CrO7
Strongest
Notes
worst for water solubility
(least polar)
best for solubility in non-polar
solvents (e.g. pentane)
–SH
O
R
Van Der Waals
(London forces)
Hydrocarbons
Strength
δ−
O
H
H
ketones, aldehydes,
esters, alkyl halides,
etc. - any molecule
with a strongly
electronegative
element (O, N, F, Cl, Br)
Attraction between
temporary dipoles
Results in trans product
H
R
Me
R
alcohol forms on most
substituted carbon
(Markovnikoff rule)
H
R Cl
Cl2, hγ
Alkyl chloride
NH4 Cl
Water, alcohols
carboxylic acids
amides, amines
Attraction between
dipole moments
caused by differences
in electronegativity
DipoleDipole
This is called ester hydrolysis
or saponification
OH
R OH
R
H2O
OH
R
H2O
OH
R
Salts
O
This is the reverse of the
above reaction.
O
NaOH
Br2
Alcohols used as solvent
Here we use water as solvent.
H2O
R
KMnO4
R
H2SO4, Δ
CH2
R
Alcohol
OMe
O
HCl
Carboxylic acid
R
(primary alcohol)
OR ketone
(secondary alcohol)
K2CrO7
R
H2SO4, Δ
H2O
Example
δ+
Attraction between
positively charged H
and negatively charged
O, N or F.
Hydrogen
Bonding
O
HCl
R
Alkene
O EtNH3
H2O
OMe
R
Ph
H2O
OMe
Attraction
between
point charges
Ionic
Found in
H
MeOH
OH
amines but NOT amides
(amides are not basic on nitrogen)
NH3Cl
Type of
Interaction
Name
O
EtNH2
R
Alkene
R
•Boiling point increases with strength of the
intermolecular interactions.
•Water solubility increases with polarity.
The Four Types of Intermolecular Bonding in Organic Chemistry
cis addition (hydrogens go
on same side of alkene)
R
HCl
O
Carboxylic
acid
Notes
HH HH
Pd/C, H2
http://masterorganicchemistry.com
(e.g. phenyl
bromide)
OH
isopropyl
e.g. isopropanol
R
R
Copyright 2012
James A.Ashenhurst
Aug 2012, version 1.1
james@masterorganicchemistry
.com
R
R
Trans
Cis
1,2
ortho
1,3
meta
1,4
para