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Homework question- alkyne synthesis

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addiemo:
Consider the transformation below and fill in the blanks with the reagents in the correct order.  The product is racemic. The starting reacant is but-1-yne and the final product is pentane-2,3-diol. Only five of the following reagents will be used to get to the final product. The reagents are: EtCl. MeOTf. Na(degree),NH3. H2, Pd/C. mCPBA. NaHSO3, H2O. H2, Lindlars. OsO4. O3. DMS. NaNH2. NaOH.

For this problem I wrote out the steps and got these reagents:
 1. NaNH2   2. EtCl   3. H2, Pd/C     4. OsO4     5. NaHSO3, H2O

However i got a 4.2/5 points so I am wondering where I might of gone wrong. Thank you!!

Babcock_Hall:
Did you count the number of carbon atoms?

rolnor:

--- Quote from: addiemo on April 28, 2024, 04:12:31 PM ---Consider the transformation below and fill in the blanks with the reagents in the correct order.  The product is racemic. The starting reacant is but-1-yne and the final product is pentane-2,3-diol. Only five of the following reagents will be used to get to the final product. The reagents are: EtCl. MeOTf. Na(degree),NH3. H2, Pd/C. mCPBA. NaHSO3, H2O. H2, Lindlars. OsO4. O3. DMS. NaNH2. NaOH.

For this problem I wrote out the steps and got these reagents:
 1. NaNH2   2. EtCl   3. H2, Pd/C     4. OsO4     5. NaHSO3, H2O

However i got a 4.2/5 points so I am wondering where I might of gone wrong. Thank you!!

--- End quote ---

Do you know what ozonolysis does? Do you know what osmium tetroxide is used for? Do you know when Lindlars catalyst is used and not Pd/C? Check wikip.

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