reaction. Use wedge and dash bonds to indicate stereochemistry where appropriate. Ignore inorganic byproducts. (and its enantiomer) under these conditions. 1. BH3-THF 2. Н,О, NaOH 1. ВН,-THF HO 1. Вн, -THF 2. H2O2, NaOH 2. Н,О,, NaOH

11. An epimerization is a reaction that changes the relative stereochemistry of one stereocenter. In the epimerization drawn below is have a higher or lower heat of combustion than Androstenediol? Explain using pictures. H3C OH H3C OH H3C H суу Н Androstanediol НО" НО H3C Н

Draw the structural formula of the product of the reaction shown below. H3C. CH3CH₂ + CH3CH₂OH **VIL • You do not have to consider stereochemistry. Na OCH₂CH3 [ ] در ? O ChemDoodle Refer

Consider the reaction of 1,2-epoxy-1-methylcyclopentane below. It can be reacted with NaOCH3 to form product 1 or with CH3OH/H* to form product 2. 1 OCH3 a OH NaOCH3 CH₂OH CH3 give OCH 3 CH3 OH b J...CH3 OH с CH3OH CH3OH₂* CH3 OCH 3 OH d 2 OCH 3 CH3 Based on the stereochemistry shown here, product 1 would be structure [Select] and product 2 would be structure [Select]