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.) H,0 OEt EtO, EtO, (2 equiv) .. a.) : OEt O: OEt EtO EIO EtO EtO H. EtO. EtO. EtO, E1O. EtO. OEt EIO EtO EIO 2 EtO EtO, OEt t EIO, OEt OE! :0: O .. OEL b.) :O: 0: OEt E10 EIO E1O EtO EtO Et EtO, EtO. EtO EtO Ot EtO EtO EtO H. OEt EtO. LOET EIO. OEt EIO EtO :o: OE c.) O .. COEt O: OEt EtO EIO E1O EtO H. EIO EtO. EtO. EtO H. OEt :O: H. : :OE 1.
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.) H,0 OEt EtO, EtO, (2 equiv) .. a.) : OEt O: OEt EtO EIO EtO EtO H. EtO. EtO. EtO, E1O. EtO. OEt EIO EtO EIO 2 EtO EtO, OEt t EIO, OEt OE! :0: O .. OEL b.) :O: 0: OEt E10 EIO E1O EtO EtO Et EtO, EtO. EtO EtO Ot EtO EtO EtO H. OEt EtO. LOET EIO. OEt EIO EtO :o: OE c.) O .. COEt O: OEt EtO EIO E1O EtO H. EIO EtO. EtO. EtO H. OEt :O: H. : :OE 1.
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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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.) H,O
OEt
EtO,
EtO,
(2 equiv)
1
O..
: OE
a.)
O:
OEt
EtO
EIO
EtO
EtO
H.
EtO.
EtO.
E1O.
EtO.
OEt
EIO
EtO
EtO
2
EtO
EtO.
OEt
t EIO,
LOEt
OEt
O
:ö:
O ..
OEL
b.)
:O:
0:
OEt
E10
EIO
E1O
EtO
EtO
Et
EtO,
EtO
EtO
EtO
Ot
EtO
EtO
EtO
H.
OEt
EtO.
LOET
EIO.
OEt
EtO
:0:
OEt
O ..
COEt
c.)
O:
OEt
10
EIO
EIO
EtO
EtO
H
EIO
EtO
EtO,
EtO
H.
OEt
:O:
H.
O:
:OE
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