[1] LIN(CH,CH3)2 HN(CH,CH3)2 LIOH [2] H,O HO, cyclohex-2-en-1-ol

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter30: Orbitals And Organic Chemistry: Pericyclic Reactions
Section30.SE: Something Extra
Problem 40AP
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Epoxides are converted to allylic alcohols with nonnucleophilic bases such as lithium diethylamide [LiN(CH2CH3)2]. Draw a stepwise mechanism for the conversion of 1,2-epoxycyclohexane to cyclohex-2en-1-ol with this base. Explain why a strong bulky base must be used in this reaction.

[1] LIN(CH,CH3)2
HN(CH,CH3)2
LIOH
[2] H,O
HO,
cyclohex-2-en-1-ol
Transcribed Image Text:[1] LIN(CH,CH3)2 HN(CH,CH3)2 LIOH [2] H,O HO, cyclohex-2-en-1-ol
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