September 28, 2024, 11:26:50 PM
Forum Rules: Read This Before Posting


Topic: Help with stereoisomers  (Read 5569 times)

0 Members and 2 Guests are viewing this topic.

Offline trinhn812

  • Regular Member
  • ***
  • Posts: 55
  • Mole Snacks: +0/-0
Help with stereoisomers
« on: September 08, 2009, 04:45:18 PM »
http://i45.photobucket.com/albums/f84/azncrombie/steromers.png

I thought it was:
i. same
ii. diastereomers
iii.enatiomers
iv.diastereomers

But it said i was wrong. Any ideas?

Offline azmanam

  • Chemist
  • Sr. Member
  • *
  • Posts: 1416
  • Mole Snacks: +160/-24
  • Mediocrity is a handrail -Charles Louis d'Secondat
Re: Help with stereoisomers
« Reply #1 on: September 08, 2009, 05:11:23 PM »
III and IV are wrong

BIG HINT: redraw one of them so it's in the same orientation as the other and looks as much as the other as possible, then do your analysis.

Knowing why you got a question wrong is better than knowing that you got a question right.

Offline Fridushka

  • Full Member
  • ****
  • Posts: 120
  • Mole Snacks: +17/-9
  • Gender: Female
Re: Help with stereoisomers
« Reply #2 on: September 09, 2009, 03:38:42 AM »
Aren't in the (i) enantiomers? or enantiomers and same..are the same  :-\ :(?!

Offline azmanam

  • Chemist
  • Sr. Member
  • *
  • Posts: 1416
  • Mole Snacks: +160/-24
  • Mediocrity is a handrail -Charles Louis d'Secondat
Re: Help with stereoisomers
« Reply #3 on: September 09, 2009, 06:05:29 AM »
they are the same molecule.... there's a special term for this case (and probably a better answer, imho).
Knowing why you got a question wrong is better than knowing that you got a question right.

Offline jj74

  • Regular Member
  • ***
  • Posts: 33
  • Mole Snacks: +1/-0
  • Gender: Male
Re: Help with stereoisomers
« Reply #4 on: September 09, 2009, 09:33:48 AM »
iv: check the configuration (R/S) of the two asymmetric carbons in the two structures

It's a town full of losers, I'm pulling out of here to win

Offline trinhn812

  • Regular Member
  • ***
  • Posts: 55
  • Mole Snacks: +0/-0
Re: Help with stereoisomers
« Reply #5 on: September 09, 2009, 01:31:10 PM »
Oh they third one fooled me. It's the same one, correct?

and the last structure, is priority OH>That long R group>CH2CH3?

For question 4, I got R and R for figure A. and R and S for figure B.

Offline trinhn812

  • Regular Member
  • ***
  • Posts: 55
  • Mole Snacks: +0/-0
Re: Help with stereoisomers
« Reply #6 on: September 09, 2009, 03:14:21 PM »
I think I'm getting more confused. Isn't ii. the same compound?

Offline Fridushka

  • Full Member
  • ****
  • Posts: 120
  • Mole Snacks: +17/-9
  • Gender: Female
Re: Help with stereoisomers
« Reply #7 on: September 09, 2009, 03:22:27 PM »
yeah i think so.., in my openion (i) is enantiomers
                                          (ii) is the same
but I'm not sure of the (iii) & (iv)..

Offline azmanam

  • Chemist
  • Sr. Member
  • *
  • Posts: 1416
  • Mole Snacks: +160/-24
  • Mediocrity is a handrail -Charles Louis d'Secondat
Re: Help with stereoisomers
« Reply #8 on: September 09, 2009, 03:39:03 PM »
i. and iii. are the same compound (although if you put 'same' you'll get the answer wrong.  there's a better descriptor that you need to use to get the answer right).

ii. and iv. are NOT the same.  You were right the first time that ii. is diastereomers.  for iv. (well, for all of them really) you should redraw them so they're at least the same projection (i.e. both line angle drawings (preferred) or both Fischer projections or whatever).  then rotate the various bonds until as many of the in-the-plane bonds in one molecule are in-the-plane in the second molecule (that is, get the two to look as much alike as possible) then do R/S  analysis on each of the chiral centers (if there are any) and evaluate.

See here for more rotation/redrawing hints:
http://www.chemicalforums.com/index.php?topic=33818.0
http://www.chemicalforums.com/index.php?topic=28328.0
http://www.chemicalforums.com/index.php?topic=32203.0
Knowing why you got a question wrong is better than knowing that you got a question right.

Offline jj74

  • Regular Member
  • ***
  • Posts: 33
  • Mole Snacks: +1/-0
  • Gender: Male
Re: Help with stereoisomers
« Reply #9 on: September 10, 2009, 06:17:36 AM »
Oh they third one fooled me. It's the same one, correct?

and the last structure, is priority OH>That long R group>CH2CH3?

For question 4, I got R and R for figure A. and R and S for figure B.


check the priorities, I think everyone has his better way of visualize molecules in three dimensions; I usually transform them in an eclipsed sawhorse projection  and then in a Fischer projection; then I find easy give the descriptors to the asymmetric carbons
It's a town full of losers, I'm pulling out of here to win

Sponsored Links