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2. Provide a mechanism for the following transformation. Make sure to account for the formation of this particular diastereomer by paying careful attention to

2. Provide a mechanism for the following transformation. Make sure to account for the formation of this

2. Provide a mechanism for the following transformation. Make sure to account for the formation of this particular diastereomer by paying careful attention to relative stereochemical relationships in all of your intermediates. Hint: Bicarbonate is not a strong enough base to deprotonate an alcohol. H OH Br NaHCO3, HO Br H H + CO + NaBr 3. Draw all possible alkenes of molecular formula C7H4 that would form 2,3-dimethylpentane upon catalytic hydrogenation (H, Pd/C). Hint: Make sure to consider both constitutional isomers and stereoisomers when formulating your answer.

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