Organic chemistry SN1 reaction's

  • #1
physstudent1
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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
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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?
 

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