Question

29 Question (2 points) a See page 1033 Predict the major organic product for the following reaction sequence, and then determine the stereochemical nature of the final product. 1) NaBH4, MeOH 2) TBDMSOCI 3) a. EtLi, b. H30+ 4) Bu4N+F 1st attempt

Answer 1

Sodium borohydride is a mild reducing agent which reduce ketone easily but not ester. NaBH4 reduces ketone to give alcohol in an enantiomeric pair. Then, the protection of alcohol is done by TBDMSC1, to prevent the attack of the nucleophilic EtLi at alcohol group. The attack of nucleophile is only on ester group. In the last step, deprotection takes place which again give alcohol in enantiomeric pair The reaction process is as follows он он 1.) NaBH4, MeOH Enantiomers он OSMDBT OH OSMDBT O 2.) TBDMSCI 3.) a. EtLi. b. H30 4.) BuNF он OH он OH Enantiomers

Therefore, the products of the given reaction are as follows: он OH он он (Part 2) Enantiomeric pair is the non-superimposable mirror image of each other Therefore, the stereochemical nature of the products formed is a pair of enantiomers is formed and option (b) is correct.