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Author Question: Arrange the following in decreasing order of their nucleophilicity. CH3CH2CH2Li, CF3CH2CH2O, ... (Read 61 times)

vinney12

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on: Aug 23, 2018
Arrange the following in decreasing order of their nucleophilicity.
  CH3CH2CH2Li, CF3CH2CH2O, CH3CH2CH2O, CH3CH2CH2S
   
  a.
  CH3CH2CH2Li > CH3CH2CH2S > CH3CH2CH2O > CF3CH2CH2O
   
  b.
  CH3CH2CH2S > CH3CH2CH2O > CF3CH2CH2O > CH3CH2CH2Li
   
  c.
  CH3CH2CH2Li > CF3CH2CH2O > CH3CH2CH2O > CH3CH2CH2S
   
  d.
  CF3CH2CH2O > CH3CH2CH2O > CH3CH2CH2S > CH3CH2CH2Li

Question 2

Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates.
 
   



Question 3

Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates.
 
   



Question 4

What is the major organic product obtained from the following reaction?
   



Question 5

What is the major organic product obtained from the following reaction?
   



Question 6

What is the major organic product obtained from the following reaction?
   



Question 7

What is the major organic product obtained from the following reaction?
   



Question 8

What is the major organic product obtained from the following reaction?
   



Question 9

What is the major organic product obtained from the following reaction?
   



Question 10

What is the major organic product obtained from the following reaction?
   



Question 11

What is the major organic product obtained from the following reaction?
   



Question 12

What is the major organic product obtained from the following reaction?
   



Question 13

What is the major organic product obtained from the following reaction?
   



Question 14

Draw all of the chloroalkanes that undergo base-promoted dehydrochlorination to form the following alkene?
   



Question 15

Draw all of the chloroalkanes that undergo base-promoted dehydrochlorination to form the following alkene?
   



Question 16

Draw all of the chloroalkanes that undergo base-promoted dehydrochlorination to form the following alkene?
   



Question 17

Draw all of the chloroalkanes that undergo base-promoted dehydrochlorination to form the following alkene?
   



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ankilker

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Reply #1 on: Aug 23, 2018
Answer to Question 1

a

Answer to Question 2

The reaction proceeds in a single step:
Concerted nucleophilic attack on the electrophilic carbon atom with departure of bromide anion as the leaving group.



Answer to Question 3

The reaction proceeds in three steps:
1. Dissociation by cleavage of the carbon-chlorine bond to afford a tertiary carbocation
2. Nucleophilic addition of water to the carbocation
3. Deprotonation of oxygen



Answer to Question 4



Answer to Question 5



Answer to Question 6



Answer to Question 7



Answer to Question 8

ANS

Answer to Question 9



Answer to Question 10



Answer to Question 11



Answer to Question 12



Answer to Question 13



Answer to Question 14



Answer to Question 15



vinney12

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Reply #2 on: Aug 23, 2018
Both answers were spot on, thank you once again


ankilker

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Reply #3 on: Aug 23, 2018
Great! Please up vote :D


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