Chemistry Reference
In-Depth Information
E1 (Unimolecular Elimination)
H
H
C
C
L
C
C+
C
C
+
+
-
H
+
L
Learning Objectives
1.
Know the meaning of: nucleophilic substitution reaction, nucleophile, substrate,
leaving group.
2.
Be familiar with the examples of nucleophilic substitution reactions listed in Table
6.1.
3.
Know the meaning of: S
N
2 mechanism, inversion of configuration, S
N
1 mechanism,
racemization, rate-determining step, E2 and E1 mechanisms.
4.
Know the formulas of carbon tetrachloride, chloroform, methylene chloride, Freons,
Halons, Teflon.
5.
Given the name of an alkyl halide or a polyhalogen compound, write its structural
formula.
6.
Given the structural formula of an alkyl halide, write a correct name for it.
7.
Write the equation for the reaction of an alkyl halide with any of the nucleophiles
listed in Table 6.1. Recognize the class of organic compound to which the product
belongs.
8.
Given the structure of an alkyl halide, predict whether it is most likely to react with
nucleophiles by an S
N
1 or an S
N
2 mechanism.
9.
Given the structure of an alkyl halide and a nucleophile, write the equations that
illustrate the formation of both the substitution and elimination products and be able
to predict which path is likely to be favored.
10.
Know the stereochemical outcome of S
N
1 and S
N
2 substitutions and E1 and E2
eliminations.
11.
Given an alkyl halide with a particular stereochemistry, a nucleophile, and reaction
conditions, predict the stereochemistry of the product of nucleophilic substitution.
12.
Combine nucleophilic substitutions with previously studied reactions to devise a
multi-step synthesis of a given product.
ANSWERS TO PROBLEMS
Problems Within the Chapter
+
_
6.1
a.
NaOH
+
CH
3
CH
2
CH
2
Br
CH
3
CH
2
CH
2
OH
+
Na Br
(item 1, Table 6.1)
