Problem Set $3$

Problem $1.$ Predict the products of each reaction in the following sequence.

${?}_{2.\text{D}\text{I}\text{B}\text{A}\text{L}-H}^{1.\text{I}\text{C}\text{P}\text{B}\text{A}}$

Problem $2.$ The following $C-H$ functionalization gives only one regiosiomeric product. Draw the key reactive

intermediate formed from the starting material, the final product, and explain the selectivity.

Problem $3.$ Sodium triacetoxyborohydride gives the trans diol selectively, but only for beta$-$hydroxy ketones. Note that

the reaction can be run using acetone as solvent. Draw a mechanism to explain the relative stereochemistry and why

it selectively reacts with this ketone instead of acetone.

Problem $4.$ A recent synthesis required the following transformation. Provide a synthetic sequence.

Problem $6.$ Provide a mechanism for the following transformation

$-$

Problem $8.$ Provide a mechanism. Hint: remember the Swern oxidation

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