E1 and Sn1
E1 and Sn1
E2
Factors affecting the type of reaction an alkyl
halide undergoes include:
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 -
OH- > F-
SN1 vs. SN2 vs. E1 vs. E2
Nucleophilicity increases from top to bottom
size increases
polarizability increases
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-
OH- or H2O
CH3OH or CH3O-
(CH3)3CO- or CH3O-
t-butoxide ion
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