Look at the given reaction and use the letter code corresponding to each compound in the blank to indicate the expected product(s) or correct vocabulary word/phrase to complete the description. If a specific stereoisomer (e.g single enantiomer) is formed, select that isomer only. If a mixture of stereoisomers (e.g. racemic or diastereomers) is formed, select the single structure that shows the appropriate mixture (e.g. lines not dashes). If we used the reagent NaOH, H_2O. The major product is compound by a(n) mechanism. On first inspection, compound appears incorrectly to be the major product, but it is prevented by difficulty getting into the transition state. If we want this compound we’d have to start with the (pick one: cis, trans) diastereomer of the original starting material. If we convert the reagent to pure H_2O. The primary products of the reaction are compounds and which are formed by and mechanisms. These products form due to an extra step in the mechanism. If this extra step did not happen we’d see compounds and as products instead. If we convert the reagent to first 1) CH_3COONa, DMSO and then 2) NaOH, H_2O: Initially we’ll form as the product after the first step by mechanism. Then we’ll form the final product by a reaction.
Expert Answer
If we used NaOH, H2O as reagent,
The major compound is C by an Sn2 mechanism.
On first inspection, compound B appears incorrectly to be major product but it is prevented by difficulty getting into the preferred transition state. If we want this compound, we’d to start with cis diastereomer of the original starting material.
If we convert the reagent to pure H2O
The primary products of the reaction are compounds D , F and O which are formed by Sn1 and E1mmechanisms. ThesThese products form due to extra rate determining step in the mechanism. If this extra step did not happhappen we’d see compouds B, C and F.
If we convert the reagent to first 1) CH3COONa and DMSO and then 2) NaOH, H2O:
Initially we’ll form J as the product after first step by Sn2 mechanism. Then we’ll form the final product B by Sn2 reaction.