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Author Question: When a student ran an asymmetric dihydroxylation reaction using cis-stilbene and the ligand ... (Read 78 times)

Pea0909berry

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When a student ran an asymmetric dihydroxylation reaction using cis-stilbene and the ligand (DHQ)2PHAL, the hydrobenzoin showed an optical rotation of 0. Explain this result.

Question 2

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 />"

Question 3

A student proposed the synthesis shown in Equation PE 14.5.
  After extraction and recrystallization, a white, flaky, crystalline product was obtained that had a melting point of 117119C. The desired product, shown in Equation PE14.5, has a melting point of 152154C. Write the structure of the compound that the student isolated and briefly explain what happened. Write a rational arrow-pushing mechanism for the formation of this product. Hint: If you were actually doing this reaction, you would have prepared a prelab writeup that included all of the physical constants for your starting materials.

Question 4

Propose three different syntheses of the alcohol shown below starting with a ketone and a Grignard reagent. In all cases, first show how you would make the Grignard reagent.
   
 

Question 5

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Answer to Question 1

The resulting diol is a meso compound and is therefore achiral, which means it must have an optical rotation of 0.

Answer to Question 2



Answer to Question 3

The product that the student obtained was 4-hydroxybenzaldehyde. This occurred because the Grignard reagent, being a strong base, deprotonated the hydroxy group in the aldehyde, resulting in the formation of benzene and the phenoxide shown below. Protonation of the phenoxide gave the aldehyde back.


Answer to Question 4






 

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