Chemistry 9701 · AS & A Level · Organic synthesis

Organic synthesis — practice question

Tartaric acid occurs in certain wines. It can be prepared in the laboratory in two stages. $\text{OHCCHO} \xrightarrow{\text{step 1}}$ intermediate $\xrightarrow{\text{step 2}} \text{HO}_2\text{CCH(OH)CH(OH)CO}_2\text{H}$. Which reagents would be suitable for this synthesis?

  • Astep 1: $\text{HCl(aq)}$; step 2: $\text{HCN(g)}$
  • Bstep 1: $\text{HCN},\ \text{NaCN(aq/alcoholic)}$; step 2: $\text{H}_2\text{SO}_4\text{(aq)}$
  • Cstep 1: $\text{H}_2\text{SO}_4\text{(aq)}$; step 2: $\text{K}_2\text{Cr}_2\text{O}_7/\text{H}_2\text{SO}_4\text{(aq)}$
  • Dstep 1: $\text{KCN(aq/alcoholic)}$; step 2: $\text{K}_2\text{Cr}_2\text{O}_7/\text{H}_2\text{SO}_4\text{(aq)}$

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