[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]

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!!

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.