0% found this document useful (0 votes)
286 views17 pages

E1 and Sn1

The document discusses factors that determine the type of substitution or elimination reaction an alkyl halide undergoes, including the type of alkyl halide, strength of the nucleophile or base, and stereochemistry. It provides guidelines for predicting whether SN1, SN2, E1, or E2 mechanisms occur based on these factors. Examples are given to illustrate key concepts like relative nucleophilicity and basicity.
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPT, PDF, TXT or read online on Scribd
0% found this document useful (0 votes)
286 views17 pages

E1 and Sn1

The document discusses factors that determine the type of substitution or elimination reaction an alkyl halide undergoes, including the type of alkyl halide, strength of the nucleophile or base, and stereochemistry. It provides guidelines for predicting whether SN1, SN2, E1, or E2 mechanisms occur based on these factors. Examples are given to illustrate key concepts like relative nucleophilicity and basicity.
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPT, PDF, TXT or read online on Scribd
You are on page 1/ 17

SN1 vs. SN2 vs. E1 vs.

E2
 Factors affecting the type of reaction an alkyl
halide undergoes include:

 Type of alkyl halide


 methyl, 1o, 2o, 3o, allylic or benzylic

 Strength of nucleophile or base


SN1 vs. SN2 vs. E1 vs. E2
 Guidelines for Predicting Products of
Substitution and Elimination Reactions:
 The strength of the nucleophile or base

determines the order of the reaction.


 S 2 and E2 reactions require strong
N
nucleophiles (or bases)

 SN1 and E1 reactions generally use weak


nucleophiles (or bases)
SN1 vs. SN2 vs. E1 vs. E2
 Nucleophilicity (nucleophile strength):
 a measure of the rate at which a nucleophile

attacks an electrophilic carbon of a


standard substrate

 A species with a negative charge is a stronger


nucleophile than a similar neutral species:
 nucleophilicity of base > conjugate acid

 CH O- > CH OH
3 3
SN1 vs. SN2 vs. E1 vs. E2
 Nucleophilicity decreases from left to right in
the periodic table
 look at the element with lone pair of e -

 more electronegative elements hold on to

electrons more tightly

 OH- > F-
SN1 vs. SN2 vs. E1 vs. E2
 Nucleophilicity increases from top to bottom
 size increases

 electrons held more loosely

 polarizability increases

 bond can begin forming when

atoms are farther apart


 I- > Br-

 Polarizable: having electrons that can move


more freely toward a positive charge
SN1 vs. SN2 vs. E1 vs. E2
SN1 vs. SN2 vs. E1 vs. E2
Example: Identify the stronger nucleophile in
each pair. Explain why.

NH3 or NH2-
H2O or NH3
HS- or Cl-
PH3 or NH3
SN1 vs. SN2 vs. E1 vs. E2
 Base Strength:
 Weaker acids produce stronger conjugate

bases.

CH3CH2OH CH3CH2O-
strong base
weak acid strong nucleophile
 Strong acids produce weak conjugate
bases.
HBr Br-

Strong acid Weak base


good nucleophile
SN1 vs. SN2 vs. E1 vs. E2
 The presence of bulky groups on the CH
nucleophile makes it less nucleophilic but3 a
stronger base. CH3 C O
 hinders approach to the electrophilic
CH3
carbon
CH3
- CH3CH2O -
CH3 C O
CH3
t-butoxide ion ethoxide ion
hindered unhindered
strong base weaker base
weak nucleophile stronger nucleophile
SN1 vs. SN2 vs. E1 vs. E2
Example: Identify the stronger base in each
pair.

OH- or H2O
CH3OH or CH3O-
(CH3)3CO- or CH3O-

Water and alcohols are amphoteric. They can


serve as either an acid or a base. Water and
alcohols are weak acids and weak bases.
SN1 vs. SN2 vs. E1 vs. E2
 Guidelines for Predicting Products of Substitution
and Elimination Reactions:
 The type of alkyl halide is important in

determining the type of reaction:


 Methyl halide: S 2 exclusively
N
 1o halide:

 S 2 with a strong nucleophile (favored)


N

 E2 with strong base (sometimes)


 SN1 or E1 are sometimes observed at high
temperatures if rearrangement produces
more stable carbonium ion
SN1 vs. SN2 vs. E1 vs. E2
 Guidelines for Predicting Products of
Substitution and Elimination Reactions:
 The type of alkyl halide is important in

determining the type of reaction:


 3o Halides:

 E2 with a strong base

 SN1 and E1 with weak nucleophile or


weak base
SN1 vs. SN2 vs. E1 vs. E2
 Guidelines for Predicting Products of Substitution
and Elimination Reactions:
 The type of alkyl halide is important in

determining the type of reaction:


 2o Halides:

 Mixtures of products are common

 Strong base/nucleophile gives SN2 and E2

 Weak base/nucleophile gives SN1 and E1


SN1 vs. SN2 vs. E1 vs. E2
 Guidelines for Predicting Products of
Substitution and Elimination Reactions:
 Strong bulky bases favor E2 reactions.

 t-butoxide ion

 Good nucleophiles with limited basicity


favor SN2 reactions.
 Br-

 I-
CH
CH
CH2OH
3 CH OH
SN1 vs. SN2 vs. E1 vs. E2
3 2

Example:
CH
CH CH
3 3
Predict
CH2OCH
2
OCH 33
the product(s) and
mechanism of the following reaction. If more
CH2 CH
CH CH2
than one
2 product
2 or mechanism is possible,
explain which is/are most likely.
CH3CH2Br CH CH2OH
+ NaOCH
3
CH3CH2Br + NaOCH33
CH3OH
CH3CH2OCH3
CH2 CH2
SN1 vs. SN2 vs. E1 vs. E2
Example: Predict the product(s) and
mechanism of the following reaction. If more
than one product or mechanism is possible,
explain which is/are most likely.
NaOCH2CH CH3 3 CH3CH
CH CH CH
CH2 2
NaOCH 2
3
CH3CHCH3
CH3CH
CH 3
CH2OH
2
OH
Br

CH3CHCH
CH 3
CHCH3 3 CH3CHCH
CH 3
CHCH3 3
Br
Br OCH2CH
OCH 2
CH3 3
SN1 vs. SN2 vs. E1 vs. E2
Example: Predict the product(s) and
mechanism of the following reaction. If more
CH3OH
than one product or mechanism is possible,
D explain which is/are most likely.

CH OH CH3
CH3 CH
3
3
OH

Br  OCH3

CH3 CH3
CH2Br CH3 OCH3 CH3
CH3
Br OCH3

You might also like

pFad - Phonifier reborn

Pfad - The Proxy pFad of © 2024 Garber Painting. All rights reserved.

Note: This service is not intended for secure transactions such as banking, social media, email, or purchasing. Use at your own risk. We assume no liability whatsoever for broken pages.


Alternative Proxies:

Alternative Proxy

pFad Proxy

pFad v3 Proxy

pFad v4 Proxy