Formation of a cis alkane from a trans alkene

In summary, the goal is to create cis-1,2-epoxy-1-phenylhexane from (E)-1-phenyl-1-hexene. The first method involves treating (E)-1-phenyl-1-hexene with H2 and poisoned Pd in Ethanol, followed by reacting it with water and heat to form a cis alkene, and then reacting it with peroxy acid in THF to form the desired product. The second method may involve using Jacobsen or Shi methods, as hinted by the teacher, and potentially reacting the cis alkene with Br2 and H2O to form the epoxy. However, the previous attempt with a cis starting material resulted in a cis product
  • #1
ahhppull
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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.
 
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  • #2
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?
 

1. How is a cis alkane formed from a trans alkene?

A cis alkane is formed from a trans alkene through a process called cis-trans isomerization. This involves breaking the double bond in the trans alkene and rearranging the atoms to form a cis alkane.

2. What is the difference between a cis alkane and a trans alkene?

A cis alkane has its hydrogen atoms on the same side of the carbon chain, while a trans alkene has its hydrogen atoms on opposite sides of the carbon chain. This results in different physical and chemical properties between the two compounds.

3. What factors influence the formation of a cis alkane from a trans alkene?

The formation of a cis alkane from a trans alkene is influenced by the type of catalyst used, the reaction conditions (such as temperature and pressure), and the size of the alkene molecule.

4. Can a trans alkene be converted back to a cis alkane?

Yes, a trans alkene can be converted back to a cis alkane through a reverse isomerization reaction. This involves breaking the double bond and rearranging the atoms to form a cis alkane.

5. What are the applications of converting a trans alkene to a cis alkane?

The conversion of a trans alkene to a cis alkane has various applications in the petrochemical industry. It can be used to produce different types of hydrocarbons, such as alkanes and alkenes, which are used as fuels and building blocks for other chemicals.

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