When diethyl succinate (1) is treated with NaOEt in EtOH, the major product is diethyl 2,5-dioxocyclohexane-1,4-dicarboxylate (2) after a mild acidic workup. Select the best detailed, step-wise, arrow-pushing mechanism for the formation of 2 from 1. 1.) NaOEt, E1OH EtO 2.) H3O+ OEt EtO. EtO. (2 equiv) 1 O.. : OEt a.) :0: OEt EtO EtO EtO EtO H. EtO. EtO. EtO EtO, OEt EtO EtO EtO EtO. EtO. EtO, LOEt OEt O :0: -ö:

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When diethyl succinate (1) is treated with NaOEt in EtOH, the major product
is diethyl 2,5-dioxocyclohexane-1,4-dicarboxylate (2) after a mild acidic
workup. Select the best detailed, step-wise, arrow-pushing mechanism for
the formation of 2 from 1.
1.) NaOEt, E1OH
EtO
2.) H30+
OEt
EtO.
EtO.
(2 equiv)
1
O..
: OEt
a.)
:0:
OEt
EtO
EtO
EtO
EtO
H.
EtO.
EtO.
EtO
EtO,
OEt
EtO
EtO
EtO
EtO.
EtO.
EtO,
COEt
OEt
O :0:
-ö:
Transcribed Image Text:When diethyl succinate (1) is treated with NaOEt in EtOH, the major product is diethyl 2,5-dioxocyclohexane-1,4-dicarboxylate (2) after a mild acidic workup. Select the best detailed, step-wise, arrow-pushing mechanism for the formation of 2 from 1. 1.) NaOEt, E1OH EtO 2.) H30+ OEt EtO. EtO. (2 equiv) 1 O.. : OEt a.) :0: OEt EtO EtO EtO EtO H. EtO. EtO. EtO EtO, OEt EtO EtO EtO EtO. EtO. EtO, COEt OEt O :0: -ö:
b.)
OEL
OEt
EtO
EtO
EtO
EtO
H.
Et
EtO,
EtO.
EtO.
EtO.
OEt
EtO
EtO
EtO
OEt
EtO.
OEt
EtO.
OEt
EtO
:
OEt
c.)
OEt
:
OEt
EtO
EtO
EtO
EtO
EtO
EtO
EtO
EtO.
OEt
C OEt
1.
O=
O
ö:
0=
O
1
Transcribed Image Text:b.) OEL OEt EtO EtO EtO EtO H. Et EtO, EtO. EtO. EtO. OEt EtO EtO EtO OEt EtO. OEt EtO. OEt EtO : OEt c.) OEt : OEt EtO EtO EtO EtO EtO EtO EtO EtO. OEt C OEt 1. O= O ö: 0= O 1
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