This question refers to the reaction depicted below, where the indicated optically active ketone undergoes base-mediated monoalkylation. Four hypothetical products have been listed, accompanied the $^1H$ $NMR$ spectrum for the major isomer.
Which compound could NOT be obtained to any extent from this reaction?
Which compound is the major product of this reaction based on the $^1H$ $NMR$ spectrum? HINT: Concentrate on the anticipated pattern for the methyl group (singlet, doublet, triplet, etc.) in the different choices.