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Organic Chemistry 2

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Moderate

Ketone alpha-Alkylation Selectivity

ORGO2-RYLFI7

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.

Created for Albert.io. Copyright 2016. All rights reserved.

Which compound could NOT be obtained to any extent from this reaction?

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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.

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Will the major isomer be optically active?

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