2 This question deals with some organic reaction mechanisms. (a) This question concerns some organic elimination reaction mechanisms. Racemic stilbene dichloride A (one enantiomer is shown) on heating with pyridine undergoes an elimination reaction to form product B. Meso-stilbene dichloride C does not undergo an elimination reaction as readily under the same conditions. Explain these results using saw-horse projections and draw mechanisms with them. Ph. H Pyridine A B Ph Pyridine H CI A Ph. H A No Reaction. CI CI Pyridine H Ph (b) (c) (d) What is the role of the pyridine in this reaction? What type of elimination reaction is this? What type of transition state does this reaction require to proceed? (e) What word describes the bond breaking and bond forming in this reaction?
2 This question deals with some organic reaction mechanisms. (a) This question concerns some organic elimination reaction mechanisms. Racemic stilbene dichloride A (one enantiomer is shown) on heating with pyridine undergoes an elimination reaction to form product B. Meso-stilbene dichloride C does not undergo an elimination reaction as readily under the same conditions. Explain these results using saw-horse projections and draw mechanisms with them. Ph. H Pyridine A B Ph Pyridine H CI A Ph. H A No Reaction. CI CI Pyridine H Ph (b) (c) (d) What is the role of the pyridine in this reaction? What type of elimination reaction is this? What type of transition state does this reaction require to proceed? (e) What word describes the bond breaking and bond forming in this reaction?
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.69P
Related questions
Question
![2
This question deals with some organic reaction mechanisms.
(a)
This question concerns some organic elimination reaction mechanisms. Racemic
stilbene dichloride A (one enantiomer is shown) on heating with pyridine undergoes an
elimination reaction to form product B. Meso-stilbene dichloride C does not undergo
an elimination reaction as readily under the same conditions. Explain these results
using saw-horse projections and draw mechanisms with them.
Ph.
H
Pyridine
A
B
Ph
Pyridine
H
CI
A
Ph.
H
A
No Reaction.
CI
CI
Pyridine
H
Ph
(b)
(c)
(d)
What is the role of the pyridine in this reaction?
What type of elimination reaction is this?
What type of transition state does this reaction require to proceed?
(e)
What word describes the bond breaking and bond forming in this reaction?](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F63c14279-1589-459a-9dfc-a501372a7d81%2F9493bf83-7e5d-439f-8ced-c3ce32df8ddf%2Fo95b9k_processed.jpeg&w=3840&q=75)
Transcribed Image Text:2
This question deals with some organic reaction mechanisms.
(a)
This question concerns some organic elimination reaction mechanisms. Racemic
stilbene dichloride A (one enantiomer is shown) on heating with pyridine undergoes an
elimination reaction to form product B. Meso-stilbene dichloride C does not undergo
an elimination reaction as readily under the same conditions. Explain these results
using saw-horse projections and draw mechanisms with them.
Ph.
H
Pyridine
A
B
Ph
Pyridine
H
CI
A
Ph.
H
A
No Reaction.
CI
CI
Pyridine
H
Ph
(b)
(c)
(d)
What is the role of the pyridine in this reaction?
What type of elimination reaction is this?
What type of transition state does this reaction require to proceed?
(e)
What word describes the bond breaking and bond forming in this reaction?
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