How come the beta position is only at the left of the Cl and not at the carbon right of the Cl?

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter30: Orbitals And Organic Chemistry: Pericyclic Reactions
Section30.SE: Something Extra
Problem 14MP: Plastic photochromic sunglasses are based on the following reversible rearrangement of a dye inside...
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How come the beta position is only at the left of the Cl and not at the carbon right of the Cl?

5302 84
Anam H
CI
Let's first consider the expected regiochemical outcome of the reaction. The reaction does not employ a sterically hind
Answer
base, so we expect the major product to be the more-substituted alkene (the Zaitsev product):
voeris
noomloti
no noitastis
100M
insmioh
Now let's consider the stereochemical outcome. In this case, the beta position (where the reaction is taking place) has only one prot
olqms
Heimodooigon
guiw
CI
ausol won
EtO
CIGM
В
Double bond
forms here
X
CIS
So, we expect this reaction to be stereospecific, rather than stereoselective. That is, we expect only one alkene, rather than a mixtur
stereoisomeric alkenes. In order to determine which alkene is obtained, we begin by drawing the Newman projection:
Crys.
dizzoq ens consulte smoa
H
CI
Me
Et
Me
This is
H
GIR
It i
on
to
P
tl
Transcribed Image Text:5302 84 Anam H CI Let's first consider the expected regiochemical outcome of the reaction. The reaction does not employ a sterically hind Answer base, so we expect the major product to be the more-substituted alkene (the Zaitsev product): voeris noomloti no noitastis 100M insmioh Now let's consider the stereochemical outcome. In this case, the beta position (where the reaction is taking place) has only one prot olqms Heimodooigon guiw CI ausol won EtO CIGM В Double bond forms here X CIS So, we expect this reaction to be stereospecific, rather than stereoselective. That is, we expect only one alkene, rather than a mixtur stereoisomeric alkenes. In order to determine which alkene is obtained, we begin by drawing the Newman projection: Crys. dizzoq ens consulte smoa H CI Me Et Me This is H GIR It i on to P tl
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