• Support PF! Buy your school textbooks, materials and every day products Here!

Formation of a cis alkane from a trans alkene

  • Thread starter ahhppull
  • Start date
  • #1
62
0

Homework Statement



Create cis-1,2-epoxy-1-phenylhexane from (E)-1-phenyl-1-hexene

Homework Equations





The Attempt at a Solution



My teacher asked for two ways to create this and I think I've got the first.

The first way was by treating (E)-1-phenyl-1-hexene with H2 and poisoned Pd in Ethanol. This creates a Cis product and then I react it with water and heat (E1 reaction) to form back an alkene but a cis alkene. Then I reacted it with peroxy acid in THF to form the product.

I'm unsure of the second way of creating this, but my teacher told us a hint and he said to look at problem 10.48 in our book. I've looked at the solution manual and they reacted the CIS alkene with Br2 and H2O and the epoxy formed by deprotonating the hydrogens on the water that attached to the alkene. In this reaction, however, a CIS starting material formed a CIS product which doesn't help me since I"m trying to form a CIS from a TRANS.
 

Answers and Replies

  • #2
chemisttree
Science Advisor
Homework Helper
Gold Member
3,316
323
That didn't stop you from converting the trans alkene first to a cis alkene in your first answer...

You allowed to use Jacobsen or Shi methods?
 

Related Threads on Formation of a cis alkane from a trans alkene

  • Last Post
Replies
9
Views
14K
  • Last Post
Replies
2
Views
1K
Replies
3
Views
1K
  • Last Post
Replies
4
Views
4K
Replies
2
Views
3K
  • Last Post
Replies
2
Views
603
  • Last Post
Replies
2
Views
3K
  • Last Post
Replies
2
Views
17K
  • Last Post
Replies
2
Views
2K
Top