4. Rose oxide is a fragrant compound found in roses and rose oil. It is synthesized industrially as a mixture of stereoisomers using the reaction below. (Only the cis isomer has the fragrant rose smell.) a) Propose a mechanism for this transformation. Is it SN1 or SN2? b) Use your mechanism to explain why a mixture of two products is formed. c) What is the stereochemical relationship between the two products? HO OH H3O+ rose oxide

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4. Rose oxide is a fragrant compound found in roses and rose oil. It is synthesized industrially as a
mixture of stereoisomers using the reaction below. (Only the cis isomer has the fragrant rose smell.)
a) Propose a mechanism for this transformation. Is it SN1 or SN2?
b) Use your mechanism to explain why a mixture of two products is formed.
c) What is the stereochemical relationship between the two products?
HO
OH
H3O+
rose oxide
Transcribed Image Text:4. Rose oxide is a fragrant compound found in roses and rose oil. It is synthesized industrially as a mixture of stereoisomers using the reaction below. (Only the cis isomer has the fragrant rose smell.) a) Propose a mechanism for this transformation. Is it SN1 or SN2? b) Use your mechanism to explain why a mixture of two products is formed. c) What is the stereochemical relationship between the two products? HO OH H3O+ rose oxide
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