2.

A Chart Comparing The SN1 vs SN2 Reactions

3. The Mechanism For The SN2 Is Concerted. The Mechanism

Of The SN1 Is Stepwise
• The SN2 reaction is concerted. That is, the SN2 occurs in one step, and both the nucleophile
and substrate are involved in the rate determining step. Therefore the rate is dependent
on both the concentration of substrate and that of the nucleophile.
• The SN1 reaction proceeds stepwise. The leaving group first leaves, whereupon a
carbocation forms that is attacked by the nucleophile.

4. The Big Barrier For The SN2 Is Steric Hindrance. The Big

Barrier For The SN1 Is Carbocation Stability
This is the most important thing to understand about each reaction. What’s the one key  factor
that can prevent this reaction from occurring?
 • In the SN2 reaction, the big barrier is steric hindrance. Since the SN2 proceeds through a
backside attack, the reaction will only proceed if the empty orbital is accessible.  The more
groups that are present around the vicinity of the leaving group, the slower the reaction will
be. That’s why the rate of reaction proceeds from primary (fastest) > secondary >> tertiary
(slowest)
• In the SN1 reaction, the big barrier is carbocation stability. Since the first step of the SN1
reaction is loss of a leaving group to give a carbocation, the rate of the reaction will be
proportional to the stability of the carbocation. Carbocation stability increases with
increasing substitution of the carbon (tertiary > secondary >> primary)  as well as with
resonance.

5. For SN2, The Rate Of Reaction Increases Going From

Tertiary To Secondary To Primary Alkyl Halides. For SN1 The
Trend Is The Opposite
• For the SN2, since steric hindrance increases as we go from primary to secondary to tertiary,
the rate of reaction proceeds from primary (fastest) > secondary >> tertiary (slowest).
• For the SN1, since carbocation stability increases as we go from primary to secondary to
tertiary, the rate of reaction for the SN1 goes from primary (slowest) << secondary < tertiary
(fastest)
Remember that SN1 and SN2 reactions only occur for alkyl halides (and related compounds like
tosylates and mesylates). If the leaving group is directly attached to an alkene or alkyne, SN1 or
SN2 will not occur!

6. The SN2 Tends To Proceed With Strong Nucleophiles. The

SN1 Tends To Proceed With Weak Nucleophiles
• The SN2 tends to proceed with strong nucleophiles; by this, generally means negatively
charged nucleophiles such as CH3O(–), CN(–), RS(–), N3(–), HO(–), and others.
• The SN1 tends to proceed with weak nucleophiles – generally neutral compounds such as
solvents like CH3OH, H2O, CH3CH2OH, and so on.

7. The SN2 Is Favored By Polar Aprotic Solvents. The SN1

Tends To Proceed In Polar Protic Solvents
• The SN2 reaction is favored by polar aprotic solvents – these are solvents such as acetone,
DMSO, acetonitrile, or DMF that are polar enough to dissolve the substrate and nucleophile
but do not participate in hydrogen bonding with the nucleophile.
• The SN1 reaction tends to proceed in polar protic solvents such as water, alcohols, and
carboxylic acids, which stabilize the resulting (charged) carbocation that results from loss of
the leaving group. These also tend to be the nucleophiles for these reactions as well.
8. When A Stereocenter Is Involved The SN2 Reaction
Provides Inversion Of Stereochemistry. The SN1 Reaction
Leads To A Mixture of Retention and Inversion
• Since the SN2 proceeds through a backside attack, if a stereocenter is present the SN2
reaction will give inversion of stereochemistry.
• By contrast, if the SN1 leads to the formation of a stereocenter, there will be a mixture
of retention and inversion since the nucleophile can attack from either face of the flat
carbocation.