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Question
The intermediate stages in the conversion:
(CH3)2−C−C−(CH3)2||OHOHdil.H2SO4⟶ΔCH3COC(CH3)3
The intermediate stages in the conversion:
(CH3)2−C−C−(CH3)2||OHOHdil.H2SO4⟶ΔCH3COC(CH3)3
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Solution
The correct options are
A (CH3)2−C−C(CH3)2||OHO⊕H2
B (CH3)2−C−⊕C(CH3)2|OH
C CH3−⊕C−C(CH3)3|OH
D CH3−C−C(CH3)3||O⊕H
This is an example of pinacol–pinacolone rearrangement.
The intermediate stages are represented by the options A, B, C, D.
In the first step, the -OH group is protonated. In the next step, a molecule of water is lost to form a carbocation intermediate which rearranges to more stable carbocation via 1,2 methyl shift. In the next step, C=O double bond is formed. The last step is deprotonation.
(CH3)2−C−C−(CH3)2||OHOHdil.H2SO4⟶Δ(CH3)2−C−C(CH3)2||OHO⊕H2→(CH3)2−C−⊕C(CH3)2|OH→CH3−⊕C−C(CH3)3|OH→CH3−C−C(CH3)3||O⊕H→CH3COC(CH3)3
A (CH3)2−C−C(CH3)2||OHO⊕H2
B (CH3)2−C−⊕C(CH3)2|OH
C CH3−⊕C−C(CH3)3|OH
D CH3−C−C(CH3)3||O⊕H
This is an example of pinacol–pinacolone rearrangement.
The intermediate stages are represented by the options A, B, C, D.
In the first step, the -OH group is protonated. In the next step, a molecule of water is lost to form a carbocation intermediate which rearranges to more stable carbocation via 1,2 methyl shift. In the next step, C=O double bond is formed. The last step is deprotonation.
(CH3)2−C−C−(CH3)2||OHOHdil.H2SO4⟶Δ(CH3)2−C−C(CH3)2||OHO⊕H2→(CH3)2−C−⊕C(CH3)2|OH→CH3−⊕C−C(CH3)3|OH→CH3−C−C(CH3)3||O⊕H→CH3COC(CH3)3
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