(b) Consider the following two elimination reactions from substrates 6 and 8. EtO HO 6 L = H or D CH3 8 Question 4 continued. ● Br OPh base. L = H or D EtOH H₂O 7 CH3 9 Page 8 of 11 + + + + EtOL O Br HOL Pho d[6] dt = KH/KD = 7.1 - Kobs [6][ Eto d[8] dt ke/kD = 0.8 = The following observations have been made about these reactions: - Kobs [8][HO Question 4 continues on the next pag CHEM30211 . Both reactions are second order overall and are first order in both substrate an PT The formation of 7 from 6 shows a strong primary kinetic isotope effect, where the formation of 9 from 8 does not show a primary kinetic isotope effect. Dissolving deuterated 8 (L = D) in basic water also produces 8 (L = H) as a by product where the deuterium label has been lost. For each of these reactions draw a mechanism and explain how each is consiste with the observations above. In each mechanism, indicate the slow step.

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Your Question:
(b) Consider the following two elimination reactions from substrates 6 and 8.
EtO
HO
6 L = H or D
CH3
8
Question 4 continued.
●
Br
OPh
base.
L = H or D
EtOH
H₂O
7
CH3
9
Page 8 of 11
+
+
+
+
EtOL
O
Br
HOL
Pho
d[6]
dt
=
KH/KD = 7.1
- Kobs [6][ Eto
d[8]
dt
ke/kD = 0.8
=
The following observations have been made about these reactions:
- Kobs [8][HO
Question 4 continues on the next pag
CHEM30211
. Both reactions are second order overall and are first order in both substrate an
PT
The formation of 7 from 6 shows a strong primary kinetic isotope effect, where
the formation of 9 from 8 does not show a primary kinetic isotope effect.
Dissolving deuterated 8 (L = D) in basic water also produces 8 (L = H) as a by
product where the deuterium label has been lost.
For each of these reactions draw a mechanism and explain how each is consiste
with the observations above. In each mechanism, indicate the slow step.
Transcribed Image Text:(b) Consider the following two elimination reactions from substrates 6 and 8. EtO HO 6 L = H or D CH3 8 Question 4 continued. ● Br OPh base. L = H or D EtOH H₂O 7 CH3 9 Page 8 of 11 + + + + EtOL O Br HOL Pho d[6] dt = KH/KD = 7.1 - Kobs [6][ Eto d[8] dt ke/kD = 0.8 = The following observations have been made about these reactions: - Kobs [8][HO Question 4 continues on the next pag CHEM30211 . Both reactions are second order overall and are first order in both substrate an PT The formation of 7 from 6 shows a strong primary kinetic isotope effect, where the formation of 9 from 8 does not show a primary kinetic isotope effect. Dissolving deuterated 8 (L = D) in basic water also produces 8 (L = H) as a by product where the deuterium label has been lost. For each of these reactions draw a mechanism and explain how each is consiste with the observations above. In each mechanism, indicate the slow step.
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