[Organic Chemistry 1:College] Predict Major Product

Click For Summary
SUMMARY

The discussion focuses on predicting the major product and identifying the reaction mechanisms (E1, E2, SN1, SN2) in organic chemistry. Participants confirmed the sequence of reactions as E2, E1, SN1, and E1, with a specific emphasis on the role of tert-butoxide as a bulky base leading to Hoffman elimination. The conversation highlights the distinction between Hoffman and Zaitsev products, clarifying that Hoffman elimination is applicable only when the leaving group is a quaternary amine. Misconceptions regarding the nomenclature of these reactions were also addressed.

PREREQUISITES
  • Understanding of organic reaction mechanisms (E1, E2, SN1, SN2)
  • Familiarity with the concept of bulky bases in elimination reactions
  • Knowledge of alkyl halides and their reactivity
  • Awareness of Hoffman elimination and Zaitsev's rule
NEXT STEPS
  • Study the mechanisms of E1 and E2 reactions in detail
  • Research the characteristics and applications of bulky bases in organic synthesis
  • Explore the differences between Hoffman and Zaitsev elimination products
  • Review organic chemistry textbooks for standardized nomenclature in reaction mechanisms
USEFUL FOR

Students and educators in organic chemistry, particularly those focusing on reaction mechanisms and elimination reactions. This discussion is beneficial for anyone looking to deepen their understanding of product prediction in organic reactions.

NY152
Messages
24
Reaction score
0

Homework Statement


Predict the major product and type of reaction mechanism (E1/E2/SN1/SN2)

Homework Equations

The Attempt at a Solution


Could someone just double check my work for this? From top to bottom I got: E2, E1, SN1, E1
 

Attachments

  • Screen Shot 2017-04-13 at 1.28.47 PM.png
    Screen Shot 2017-04-13 at 1.28.47 PM.png
    5.3 KB · Views: 571
Physics news on Phys.org
Looks good, but you permuted the last two solutions in the graph.
 
NY152 said:

Homework Statement


Predict the major product and type of reaction mechanism (E1/E2/SN1/SN2)

Homework Equations

The Attempt at a Solution


Could someone just double check my work for this? From top to bottom I got: E2, E1, SN1, E1
I think it should be E2(strong base), E2(strong bulky base does E2 hoffman elimination ), E1 and Acid-base reaction followed by Sn1. The bottom two images are shifted tho
 
Why do continue to refer to E1/E2 eliminations involving alkyl halides as “Hoffman elimination”?
 
chemisttree said:
chemisttree said:
Why do continue to refer to E1/E2 eliminations involving alkyl halides as “Hoffman elimination”?
The second option has tertbutoxide which is a bulky base, it is said to do E2 elimination to form the less stable alkene. Hence Hoffman elimination product is dominant over the zaitsev so it's also called Hoffman Elimination in various chem texts.
 
ONLY if the leaving group is a quaternary amine. There are no organic chemistry books that label alkyl halide reactions with strong bases as “Hoffman”.
 
chemisttree said:
ONLY if the leaving group is a quaternary amine. There are no organic chemistry books that label alkyl halide reactions with strong bases as “Hoffman”.
By hoffman elimination, I simply mean that the product is a Hoffman product.
 
That's not a standard nomenclature and can be misleading and confusing.
 

Similar threads

Is E1 or E2 the Correct Mechanism for Bulky Base Eliminations?
  • · Replies 3 ·
Replies
3
Views
3K
Which Major Pathway Predominates for This Organic Reaction?
  • · Replies 2 ·
Replies
2
Views
3K
Organic Chemistry: Sn1/E1/Sn2/E2/Alchol/Ether Transformations
  • · Replies 3 ·
Replies
3
Views
8K
Ochem: H2O & HBr Reactions 2nd Semester Organic Chemistry
  • · Replies 1 ·
Replies
1
Views
5K
Elimination reactions of cyclohexane derivatives
  • · Replies 25 ·
Replies
25
Views
5K
OCHEM SN1 and SN2 Major Products
  • · Replies 1 ·
Replies
1
Views
3K
What will be the product of this organic reaction?
  • · Replies 28 ·
Replies
28
Views
5K
What is the Major Product When Furan Reacts with Chloroform?
  • · Replies 6 ·
Replies
6
Views
4K
Which Product Won't Be Obtained in a Wurtz Reaction?
  • · Replies 11 ·
Replies
11
Views
3K
SN1 Rxn: is hyrdride shift major product or the LG position?
  • · Replies 1 ·
Replies
1
Views
2K