This topic contains a solution. Click here to go to the answer

Author Question: When a student ran an asymmetric dihydroxylation reaction using cis-stilbene and the ligand ... (Read 61 times)

Pea0909berry

  • Hero Member
  • *****
  • Posts: 573
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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



Related Topics

Need homework help now?

Ask unlimited questions for free

Ask a Question
Marked as best answer by a Subject Expert

Chou

  • Sr. Member
  • ****
  • Posts: 335
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






 

Did you know?

Hypertension is a silent killer because it is deadly and has no significant early symptoms. The danger from hypertension is the extra load on the heart, which can lead to hypertensive heart disease and kidney damage. This occurs without any major symptoms until the high blood pressure becomes extreme. Regular blood pressure checks are an important method of catching hypertension before it can kill you.

Did you know?

Drying your hands with a paper towel will reduce the bacterial count on your hands by 45–60%.

Did you know?

Methicillin-resistant Staphylococcus aureus or MRSA was discovered in 1961 in the United Kingdom. It if often referred to as a superbug. MRSA infections cause more deaths in the United States every year than AIDS.

Methicilli ...
Did you know?

Chronic marijuana use can damage the white blood cells and reduce the immune system's ability to respond to disease by as much as 40%. Without a strong immune system, the body is vulnerable to all kinds of degenerative and infectious diseases.

Did you know?

About 600,000 particles of skin are shed every hour by each human. If you live to age 70 years, you have shed 105 pounds of dead skin.

For a complete list of videos, visit our video library