The product shown can be synthesized by two different pathways as ...

[OSWALD]

The product shown can be synthesized by two different pathways as shown by the reaction conditions. Draw the structure of starting materials that should be placed in each of the boxes.
 
   

Question 2

Which of the following would represent the correct reaction conditions for the following conversion?
 
   

   
  a.
  1) KMnO₄, 2) LiAlH₄
   
  b.
  1) Mg, ether, 2) CO₂, 3) LiAlH₄
   
  c.
  1) NaOH, H₂O, 2) LiAlH₄
   
  d.
  1) SOCl₂, benzene, 2) LiAlH₄
   
  e.
  either b or c

Question 3

Instructions: Carboxylic acids are synthesized from alkyl halides via Grignard reagent carboxylation or nitrile hydrolysis. Choose the best method for affecting each of the following conversions. Explain each of your choices. If neither method is appropriate, explain.
 

Complete the following reaction sequence with the missing major organic products.
 
   

Question 4

Instructions: Carboxylic acids are synthesized from alkyl halides via Grignard reagent carboxylation or nitrile hydrolysis. Choose the best method for affecting each of the following conversions. Explain each of your choices. If neither method is appropriate, explain.
 

Choose best method:
 
   

Question 5

Instructions: Carboxylic acids are synthesized from alkyl halides via Grignard reagent carboxylation or nitrile hydrolysis. Choose the best method for affecting each of the following conversions. Explain each of your choices. If neither method is appropriate, explain.
 

Choose best method:
 
   

Question 6

Instructions: Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry.
 

Refer to instructions and answer the following questions.
   

  a)
 

Give major product(s):
 
   

   
   
  b)
  Draw the structure of the intermediate product(s) that form(s).

Question 7

Instructions: Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry.
 

Give major product(s):
 
   

Question 8

Instructions: Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry.
 

Give major product(s):
 
   

Question 9

Instructions: Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry.
 

Give major product(s):
 
   

[apple]

Answer to Question 1



Answer to Question 2

c

Answer to Question 3



Answer to Question 4

Amine protons interfere with the formation of Grignard reagents, so nitrile hydrolysis is the best method for carrying out this conversion.

Answer to Question 5

Since S_N2 displacements do not occur at tertiary alkyl halides, the Grignard reagent carboxylation is the best method for carrying out this conversion.

Answer to Question 6

a)


b)


Answer to Question 7



Answer to Question 8



Answer to Question 9

[OSWALD]

Excellent

[Joy Chen]

TYSM