CHEM 2251
Problem Set 5
Vaughn
1. Consider the molecule shown below. [1] Draw the two chair conformations for the compound.
[2] Identify which of the two chair conformations is more stable and explain why.
H
in
ÉtÉ
2. How are the following molecules related? (exactly the same, completely different, constitutional
isomers, enantiomers, or diastereomers).
d
Mon
Non
same
oralwhy
constitutional
enantiomer
isomer
diastereomers
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CHEM 2251
Problem Set 5
Vaughn
3. Identify all stereocenters in the following molecules as R or S.
3C
i
unit
j
4
Ipa
i
3
R
R R
R
4. Consider the following reaction. This reaction is a multi-step reaction.
[1] Draw the mechanism for each step of this reaction using curved arrow notation, include all lone
pairs of electrons if they are directly involved in the reaction.
[2] Identify the arrow pushing pattern (mechanistic pattern: nucleophilic attack, loss of leaving
group, or proton transfer) for each step.
[3] Draw a transition state for each step.
H
Proton transfer
it
Nucleophilic
attack
at
y
mn
deprotonation
CH
Ct's
No
H
This content is protected and may not be shared, uploaded or distributed
as o
H
would
LPartial
0
have
charge
a
I