When (C) (2,3-dimethylbutane-2,3-diol) is heated in acid, the only product is (D) (2,3-dimethylbutane-2-one), as shown at the right. HO OH H3C-C-C-CH3 H3C CH3 (C) Give a detailed, stepwise mechanism that accounts for the formation of (D) from (C) When cyclobutene-1,2-bis(methylcarboxylate) (E) is heated in the presence of maleic anhydride, the only product is 8-oxabicyclo- [4.3.0]nonan-3-en-7,9-dione-3,4-bis(methylcarboxylate) (F), as CO₂CH3 O CH3 H* H3C-C-C-CH3 + H₂O A CH3 (D) ° ° CO₂CH3 A CO₂CH3 CO₂CH3 (E) (F) Give a mechanistic explanation for how (F) is formed from (E). FYI: More than one step is required. shown at the right.

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Please draw out both mechanisms

When (C) (2,3-dimethylbutane-2,3-diol) is heated in acid, the only
product is (D) (2,3-dimethylbutane-2-one), as shown at the right.
HO OH
H3C-C-C-CH3
H3C CH3
(c)
Give a detailed, stepwise mechanism that accounts for the formation of (D) from (C)
When cyclobutene-1,2-bis(methylcarboxylate) (E) is heated in the
presence of maleic anhydride, the only product is 8-oxabicyclo-
[4.3.0]nonan-3-en-7,9-dione-3,4-bis(methylcarboxylate) (F), as
O CH3
H3C-C-C-CH3 + H2O
CH3
H+
A
(D)
CO₂CH3
CO₂CH3
CO₂CH3
CO₂CH3
(E)
(F)
Give a mechanistic explanation for how (F) is formed from (E). FYI: More than one step is required.
shown at the right.
Transcribed Image Text:When (C) (2,3-dimethylbutane-2,3-diol) is heated in acid, the only product is (D) (2,3-dimethylbutane-2-one), as shown at the right. HO OH H3C-C-C-CH3 H3C CH3 (c) Give a detailed, stepwise mechanism that accounts for the formation of (D) from (C) When cyclobutene-1,2-bis(methylcarboxylate) (E) is heated in the presence of maleic anhydride, the only product is 8-oxabicyclo- [4.3.0]nonan-3-en-7,9-dione-3,4-bis(methylcarboxylate) (F), as O CH3 H3C-C-C-CH3 + H2O CH3 H+ A (D) CO₂CH3 CO₂CH3 CO₂CH3 CO₂CH3 (E) (F) Give a mechanistic explanation for how (F) is formed from (E). FYI: More than one step is required. shown at the right.
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