September 16, 2024, 04:26:09 PM
Forum Rules: Read This Before Posting


Topic: homework help: im not seeing why this Sn1 reaction is doing  (Read 2327 times)

0 Members and 1 Guest are viewing this topic.

Offline frankenstein18

  • Regular Member
  • ***
  • Posts: 9
  • Mole Snacks: +0/-0
homework help: im not seeing why this Sn1 reaction is doing
« on: November 15, 2015, 12:41:04 AM »


In Sn1 reactions with asymmetric centers, the products are supposed to be enantiomers

in the reaction in the image (which you can hopefully see. if not its a cyclopentane with a Ph and a Me attached on carbon one, the Ph is toward the front and the Me is toward the back, and the same thing is happening on Carbon 3)

the products formed when it reacts with Iodine are not enantiomers, right?

how can that be possible if there are assymetric centers

how are they not enantiomers? I think they are but my professor said they weren't

Offline kriggy

  • Chemist
  • Sr. Member
  • *
  • Posts: 1520
  • Mole Snacks: +136/-16
Re: homework help: im not seeing why this Sn1 reaction is doing
« Reply #1 on: November 15, 2015, 05:29:16 AM »
What is definition of enantiomer?

Offline frankenstein18

  • Regular Member
  • ***
  • Posts: 9
  • Mole Snacks: +0/-0
Re: homework help: im not seeing why this Sn1 reaction is doing
« Reply #2 on: November 15, 2015, 11:03:57 AM »
What is definition of enantiomer?

Non-superimposable mirror images.

Ok I think I understand they aren't mirror images of themselves so they are not enantiomers

Are they same compound then?

So it's possible to have an Sn1 reaction where no enantiomers are formed? Like in this one?


Offline kriggy

  • Chemist
  • Sr. Member
  • *
  • Posts: 1520
  • Mole Snacks: +136/-16
Re: homework help: im not seeing why this Sn1 reaction is doing
« Reply #3 on: November 15, 2015, 11:28:22 AM »

Offline beardy

  • Regular Member
  • ***
  • Posts: 42
  • Mole Snacks: +0/-0
  • Gender: Male
Re: homework help: im not seeing why this Sn1 reaction is doing
« Reply #4 on: November 20, 2015, 05:35:53 PM »
The reactant had two chiral centers. The left one remained untouched. The chirality of that chiral center is still the same after product formation. That's essentially a diastereomer.

Here's a visual,




Source: http://chemwiki.ucdavis.edu/Organic_Chemistry/Organic_Chemistry_With_a_Biological_Emphasis/Chapter_03%3A_Conformations_and_Stereochemistry/Section_3.7%3A_Diastereomers

Sponsored Links