Optically pure product

Discussion in 'DAT Discussions' started by koreano, 07.12.12.

  1. SDN is made possible through member donations, sponsorships, and our volunteers. Learn about SDN's nonprofit mission.
  1. koreano

    koreano 5+ Year Member

    Joined:
    06.03.11
    Messages:
    559
    Status:
    Dental Student
    Verified
    Navy

    SDN Members don't see this ad. About the ads.
    I just finished DAT qVAULT orgo test #2 and there is one question that I can't seem to wrap my head around... The question asks, Which of the following reactions will give an optically pure product? And the answer is 2-chloro pentane reacting with NaCN... Can someone explain to me why this is the case?
     
  2. SDN Members don't see this ad. About the ads.
  3. koreano

    koreano 5+ Year Member

    Joined:
    06.03.11
    Messages:
    559
    Status:
    Dental Student
    Verified
    Navy
    Does optically pure product refer to a product that only has ONE chiral center...?
     
  4. ktran17

    ktran17 5+ Year Member

    Joined:
    04.12.11
    Messages:
    1,187
    Location:
    socal
    Status:
    Dental Student
    Verified
    Army
    read the question wrong =P.. sorry

    was reviewing my notes for chad at the same time and was on the optically inactive section XD
     
    Last edited: 07.12.12
  5. ah7391

    ah7391 Banned

    Joined:
    10.23.11
    Messages:
    51
    No that's wrong.

    Optically pure means it only has one enantiomer. Since this reaction undergoes sn2 -CN is a typical substitution nucleophile for sn2 chemistry then it forms the inverse product only. All the product will have one chiral center.

    Basically you wont have a racemic mixture at all (when both enantiomers are in solution like sn1 chemistry does)
     
  6. koreano

    koreano 5+ Year Member

    Joined:
    06.03.11
    Messages:
    559
    Status:
    Dental Student
    Verified
    Navy
    But when you react 2-chloro pentane with NaCN, dont you get 2-methyl-1-pentamine, which has a chiral center at carbon #2?
     
  7. ah7391

    ah7391 Banned

    Joined:
    10.23.11
    Messages:
    51
    And optically INACTIVE is when the product is achiral (or meso, watch out for those!)
     
  8. koreano

    koreano 5+ Year Member

    Joined:
    06.03.11
    Messages:
    559
    Status:
    Dental Student
    Verified
    Navy
    I thought so... Thanks ah7391
     
  9. ah7391

    ah7391 Banned

    Joined:
    10.23.11
    Messages:
    51
    Np! Thank chad!
     

About the ads

Share This Page