× Didn't find what you were looking for? Ask a question
Top Posters
Since Sunday
j
4
m
4
n
3
m
3
R
3
V
3
e
3
w
3
j
3
a
3
a
3
h
3
New Topic  
datty117 datty117
wrote...
Posts: 94
Rep: 1 0
11 years ago
why is vinyl chloride is nonreactive to nucleophilic substitution reactions?
Read 1274 times
1 Reply

Related Topics

Replies
wrote...
11 years ago
Nucleophilic substitution via the SN1 or SN2 mechanism does not occur with vinyl chloride (or other vinyl halides or aryl halides) as it has an unsaturated carbon centre. So the bond between the chlorine and the carbon in the double bond is much too strong - stronger than that of an alkyl chloride - to be broken by a nucleophile (SN2). Also the electrons of the double bond repel the approach of a nucleophile.
Vinyl chloride does not undergo an SN1 reaction either because the carbocation intermediate it would produce would be far too unstable and so is not readily formed.
New Topic      
Explore
Post your homework questions and get free online help from our incredible volunteers
  924 People Browsing
Related Images
  
 215
  
 86
  
 438
Your Opinion
Which industry do you think artificial intelligence (AI) will impact the most?
Votes: 405