Solvents

A solvent is a liquid that serves as the medium for a reaction. It can serve two
major purposes:
1. (Non-participatory) to dissolve the reactants. Rememer !li"e dissolves
li"e#$ %olar solvents are est for dissolvin& polar reactants (such as ions)'
nonpolar solvents are est for dissolvin& nonpolar reactants (such as
hydrocarons).
(. %articipatory: as a source of acid (proton)) base (removin& protons)) or as
a nucleophile(donatin& a lone pair of electrons). *he only class of solvents for
which this is somethin& you &enerally need to worry aout are polar protic
solvents (see elow).
+,. -o what does !polar# and !non-polar# mean$
Polar solvents have lar&e dipole moments (a"a !partial char&es#)' they
contain onds etween atoms with very different electrone&ativities) such as
o.y&en and hydro&en.
Non polar solvents contain onds etween atoms with similar
electrone&ativities) such as caron and hydro&en (thin" hydrocarons) such as
&asoline). /onds etween atoms with similar electrone&ativities will lac" partial
char&es' it0s this asence of char&e which ma"es these molecules !non-polar#.
*here are two common ways of measurin& this polarity. +ne is throu&h
measurin& a constant called !dielectric constant# or permitivity. *he &reater the
dielectric constant) the &reater the polarity (water 1 hi&h) &asoline 1 low). A
second comes from directly measurin& the dipole moment.
*here0s a final distinction to e made and this causes confusion. -ome solvents
are called !protic# and some are called !aprotic#. 2hat ma"es a solvent a !protic#
solvent) anyway$
Protic solvents have +-3 or N-3 onds. 2hy is this important$ /ecause
protic solvents can participate in hydro&en ondin&) which is a powerful
intermolecular force. Additionally) these +-3 or N-3 onds can serve as a
source of protons (34).
Aprotic solvents may have hydro&ens on them somewhere) ut they lac"
+-3 or N-3 onds) and therefore cannot hydrogen bond with themselves.
5or the avera&e first semester student) these distinctions come up the most in
sustitution reactions) where hydro&en ondin& solvents tend to decrease the
reactivity of nucleophiles' polar aprotic solvents) on the other hand) do not.
*here are 6 types of solvents commonly encountered: nonpolar) polar aprotic) and
polar protic. (*here ain0t such a thin& as a non-polar protic solvent).
+,) enou&h yammerin&. 3ere are some (hopefully useful) tales.
Nonpolar solvents:
*hese solvents have low dielectric constants (78) and are not &ood solvents for
char&ed species such as anions. 3owever diethyl ether (9t(+) is a common
solvent for :ri&nard reactions' its lone pairs are ;ewis asic and can help to
solvate the <& cation.
Borderline Polar aprotic solvents
*hese solvents have moderately hi&her dielectric constants than the nonpolar
solvents (etween 8 and (=). -ince they have intermediate polarity they are &ood
!&eneral purpose# solvents for a wide ran&e of reactions. *hey are !aprotic#
ecause they lac" +-3 or N-3 onds. 5or our purposes they don0t participate in
reactions: they serve only as the medium.

Polar aprotic solvents
*hese solvents all have lar&e dielectric constants (>(=) and lar&e dipole moments)
ut they do not participate in hydro&en ondin& (no +-3 or N-3 onds). *heir hi&h
polarity allows them to dissolve char&ed species such as various anions used as
nucleophiles (e.&. ?N(-)) 3+(-)) etc.). *he lac" of hydro&en ondin& in the solvent
means that these nucleophiles are relatively !free# in solution) ma"in& them more
reactive. 5or our purposes these solvents do not participate in the reaction.
Polar protic solvents
%olar protic solvents tend to have hi&h dielectric constants and hi&h dipole
moments. 5urthermore) since they possess +-3 or N-3 onds) they can also
participate in hydro&en ondin&. *hese solvents can also serve as acids (sources
of protons) and wea" nucleophiles (formin& onds with stron& electrophiles).
*hey are most commonly used as the solvent for their conju&ate ases. (e.&. 3(+
is used as the solvent for 3+(-)' 9t+3 is used as the solvent for 9t+(-). )
*hese types of solvents are y far the most li"ely to participate in reactions. *here
are many e.amples (too many to list) where a polar protic solvent such as water)
methanol) or ethanol can serve as the nucleophile in a reaction) often when a
stron& electrophile (such as an acid) is present. -o if you see this type of solvent)
e on the loo"out.