Researchers studying the structures of terpene samples isolated from natural sources often carry out reaction sequences...

  

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Researchers studying the structures of terpene samples isolated from natural sources often carry out reaction sequences intended to correlate a new structure with a previously identified one, verifying that the stereochemistry matches. One such sequence that researchers carried out is shown below, starting from ẞ-eudesmol and resulting in cryptomeridiol stereoisomers. Fill in the missing structures (one structure per box). ẞ-eudesmol OH 1. LiAlH4 2. H₂O workup 1. LiAlH4 2. H₂O workup HO cryptomeridiol OH OH HO 4-epi-cryptomeridiol Researchers studying the structures of terpene samples isolated from natural sources often carry out reaction sequences intended to correlate a new structure with a previously identified one, verifying that the stereochemistry matches. One such sequence that researchers carried out is shown below, starting from ẞ-eudesmol and resulting in cryptomeridiol stereoisomers. Fill in the missing structures (one structure per box). ẞ-eudesmol OH 1. LiAlH4 2. H₂O workup 1. LiAlH4 2. H₂O workup HO cryptomeridiol OH OH HO 4-epi-cryptomeridiol