Organic Chemistry

posted by .

1,4-Diphenyl-1,3-butadiene was synthesied using cinnamaldehyde, K3PO4, and benzyltriphenylphosphonium chloride.

In addition to cis,trans and trans,trans-1,4-Diphenyl-1,3-butadiene, there is another isomer of this compound that has not been shown. What is it and why was it not produced? (Hint: Cinnamaldehye has trans stereochemistry)

  • Organic Chemistry -

    It is most likely cis,cis-1,4-dephenyl-1,3-butadiene. If you draw it you would see a U-shaped molecule with the two phenyl groups getting close together at the the ends of the "U". Formation of this isomer is probably prevented by crowding (steric hindrance) at the ends of the U-shaped structure.

  • Organic Chemistry -

    Another argument I just overlooked is that one of the reactants, cinnamaldehyde, contains a trans structure around the c=c double bond that is preserved in the final compound, 1,4-Diphenyl-1,3-butadiene. Thus, we cannot have two cis structures in the C=C-C=C chain which is the backbone of the the final compound. This may be a better argument than the one in my previous answer.

Respond to this Question

First Name
School Subject
Your Answer

Similar Questions

  1. Chemistry

    Below is the question I am trying to answer. I think after much debate, I may have it. Does anyone know if I am close to being right?
  2. Chemistry

    Below is the question I am trying to answer. I think after much debate, I may have it. Does anyone know if I am close to being right?
  3. organic chemistry

    why is the trans-trans isomer of dibenzalacetone the most stable isomer?
  4. Organic Chemistry

    In order for a Diels-Alder reaction to take place the diene must be in what conformation?
  5. chemistry

    Why are cis and trans isomers not possible for ClCH2CH2Cl?
  6. Chemistry

    If I react a phosphorus ylide with trans-cinnamaldehyde, what would the ratio of trans-trans to cis-trans isomer would I likely get?
  7. chemistry

    What reagents would I have to use to convert a trans alkene into a cis alkene?
  8. TO M--urgent

    I named that compound as cis and it should be trans. The I atoms are on opposite sides and that's trans, not cis.
  9. Organic Chemistry

    Which isomer of 1-ethyl-3-methylcyclohexane is more stable, cis or trans?
  10. organic chemistry

    is 2-pentene a cis or trans? and why? Cis- atleast 2 bulky grps.. Trans-3-4 bulky grps.. cis and trans must contain a double bond. i don't know if its a cis or trans so please enlighten me

More Similar Questions