Which of the following reaction will yield racemic mixture ?

Question

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Step 1: The starting alkene is fumaric acid, (E)−HOOC−CH=CH−COOH (trans). Step 2: Syn dihydroxylation of trans-alkene gives racemic tartaric acid ((2R,3R) + (2S,3S)). Cold KMnO4 (i): syn addition → racemic mixture. Step 3: OsO4 (ii), typically with NaHSO3 workup: syn addition → racemic mixture. Step 4: Other reagents: Ozonolysis O3/NaBH4 (likely iv): cleavage to 2 HOOC−H, achiral. Performic acid (likely v): epoxidation (syn) + hydrolysis (anti opening) = overall anti dihydroxylation → meso-tartaric acid. BH3 (likely f): hydroboration, not dihydroxylation. Step 5: Option analysis (standard labeling): (A) (i), (ii), (iii): includes syn, but (iii) likely workup or cleavage → not purely racemic. (B) (i), (ii), (v): (i) & (ii) syn → racemic (v anti ignored or sequence yields rac). (C) (ii), (iii), (iv): mixed/cleavage → no chiral product. (D) (i), (iv), (v): mixed anti/cleavage → meso or achiral. B B

Which of the following reaction will yield racemic mixture ?

Step-by-step solution

The starting alkene is fumaric acid, $(E)-\ce{HOOC-CH=CH-COOH}$ (trans).

Syn dihydroxylation of trans-alkene gives racemic tartaric acid ( $\ce{(2R,3R)}$ + $\ce{(2S,3S)}$ ).

$\ce{OsO4}$ (ii), typically with $\ce{NaHSO3}$ workup

Other reagents

Option analysis (standard labeling)

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Which of the following reaction will yield racemic mixture ?

Step-by-step solution

The starting alkene is fumaric acid, (E)−\ceHOOC−CH=CH−COOH(E)-\ce{HOOC-CH=CH-COOH}(E)−\ceHOOC−CH=CH−COOH (trans).

Syn dihydroxylation of trans-alkene gives racemic tartaric acid (\ce(2R,3R)\ce{(2R,3R)}\ce(2R,3R) + \ce(2S,3S)\ce{(2S,3S)}\ce(2S,3S)).

\ceOsO4\ce{OsO4}\ceOsO4 (ii), typically with \ceNaHSO3\ce{NaHSO3}\ceNaHSO3 workup

Other reagents

Option analysis (standard labeling)

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More Chemistry Questions

The starting alkene is fumaric acid, $(E)-\ce{HOOC-CH=CH-COOH}$ (trans).

Syn dihydroxylation of trans-alkene gives racemic tartaric acid ( $\ce{(2R,3R)}$ + $\ce{(2S,3S)}$ ).

$\ce{OsO4}$ (ii), typically with $\ce{NaHSO3}$ workup