Organic chemistry SN1 reaction's

  • #1
270
1

Homework Statement



Find the major organic product B of http://www.webassign.net/userimages/kasandbe/CH221_ssii_02/CH221_exam2_ssii_02_7a.gif

(with ethanol at 0 degrees Celsius)

Homework Equations





The Attempt at a Solution



I thought that since it is a SN1 reaction the -OTs would be the LG and that -OCH2CH3 would connect to the carbon it was on and form a racemic mixture but this isn't the right answer can anyone clear this up I seem to be confused? Thanks.
 

Answers and Replies

  • #2
chemisttree
Science Advisor
Homework Helper
Gold Member
3,616
637
That's certainly possible but only as a minor product. You will note that in this SN1 reaction, OTs- is indeed the leaving group. Study the carbonium ion that results. It is a secondary carbonium ion next to a 3o carbon and a 1o carbon. What might happen?
 

Related Threads on Organic chemistry SN1 reaction's

Replies
3
Views
7K
  • Last Post
Replies
1
Views
1K
  • Last Post
Replies
5
Views
2K
  • Last Post
Replies
1
Views
2K
  • Last Post
Replies
1
Views
818
D
  • Last Post
Replies
2
Views
2K
Replies
2
Views
1K
  • Last Post
Replies
1
Views
565
Replies
16
Views
2K
Replies
8
Views
977
Top