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DLS

Organic chemistry

  • one year ago
  • one year ago

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  1. DLS
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    Which carbo cation is least likely to form as as intermediate? |dw:1360852772005:dw|

    • one year ago
  2. shubhamsrg
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    D) maybe ?

    • one year ago
  3. shubhamsrg
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    A) is 3 degree and so is C)

    • one year ago
  4. shubhamsrg
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    B is 2 degree, also has a double bond which adds to the stability

    • one year ago
  5. DLS
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    its definitely not A for sure

    • one year ago
  6. DLS
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    C is not 3 degree i guess

    • one year ago
  7. shubhamsrg
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    C is attached to 3 carbons ?

    • one year ago
  8. DLS
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    its bridgehead

    • one year ago
  9. shubhamsrg
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    hmm ? well still there are 3 carbons !

    • one year ago
  10. shubhamsrg
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    If i had to put a guess, I'd say D)

    • one year ago
  11. DLS
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    ITS C DAMMIT

    • one year ago
  12. shubhamsrg
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    hmm,, sorry about that then! :|

    • one year ago
  13. DLS
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    man I really thought u shud know all that before 2 months of JEE LOL

    • one year ago
  14. DLS
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    hmm okay sorry :P

    • one year ago
  15. shubhamsrg
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    Wish your thinking was true!

    • one year ago
  16. shubhamsrg
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    Well I have never seen a bridged carbocation before.

    • one year ago
  17. DLS
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    are u freaking kidding me ._.

    • one year ago
  18. shubhamsrg
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    On a bridge head a positive carbon never occurs ~Wikipedia

    • one year ago
  19. shubhamsrg
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    http://en.wikibooks.org/wiki/Organic_Chemistry/Introduction_to_reactions/Carbocations

    • one year ago
  20. DLS
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    so what :P

    • one year ago
  21. shubhamsrg
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    hmm, that is why it must be least likely to form! hmm, seems legit

    • one year ago
  22. DLS
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    wtf

    • one year ago
  23. shubhamsrg
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    :)

    • one year ago
  24. DLS
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    whaaaaaaaaaaat

    • one year ago
  25. DLS
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    thoda detail zara?

    • one year ago
  26. shubhamsrg
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    well since bridged carbocation is not formed, hence it is least likely to be formed here.

    • one year ago
  27. shubhamsrg
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    never formed*

    • one year ago
  28. DLS
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    i asked why it isnt form ._. i dont want to accept it as a fact

    • one year ago
  29. DLS
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    formed*

    • one year ago
  30. shubhamsrg
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    I don't know the fact! I just learnt it!

    • one year ago
  31. shubhamsrg
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    reason of the fact*

    • one year ago
  32. DLS
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    \m/

    • one year ago
  33. shubhamsrg
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    Here, you may read this, this has the reason http://www.tricity.wsu.edu/Chem540/ar00096a001.pdf

    • one year ago
  34. DLS
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    god i cant read that whole thing :/

    • one year ago
  35. shubhamsrg
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    learn as fact! thats what I just did !

    • one year ago
  36. shubhamsrg
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    In chem, most of times, there aren't reasons, there are rules, !

    • one year ago
  37. DLS
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    rehne de be :P

    • one year ago
  38. shubhamsrg
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    sure! :D

    • one year ago
  39. DLS
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    http://fc06.deviantart.net/fs70/f/2011/288/3/c/nothing_to_do_here_by_rober_raik-d4cxltj.png

    • one year ago
  40. shubhamsrg
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    http://narwhaler.com/img/ys/x/i-see-your-point-spear-spiderman-YsX3vo.jpg

    • one year ago
  41. Yahoo!
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    Shuld nt the answer be D............

    • one year ago
  42. chmvijay
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    i think answer is D

    • one year ago
  43. DLS
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    its C

    • one year ago
  44. DLS
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    and its proven I guess

    • one year ago
  45. DLS
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    @abb0t

    • one year ago
  46. abb0t
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    If (A) is benzene, then it's (D). Remember you can't form primary carbocations ever.

    • one year ago
  47. DLS
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    answer is C?

    • one year ago
  48. DLS
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    wikipedia says too..

    • one year ago
  49. DLS
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    but i want smt more detailed

    • one year ago
  50. abb0t
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    Wikipedia says the answer is C?

    • one year ago
  51. DLS
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    On a bridge head a positive carbon never occurs ~Wikipedia

    • one year ago
  52. abb0t
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    The + isn't on the bridge though.

    • one year ago
  53. DLS
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    that is why it cant resonate,the charge is localized.

    • one year ago
  54. DLS
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    so isnt C in a worse condition than D? it cant resonate at all but D still can

    • one year ago
  55. abb0t
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    Resonance is not the same as formation of a carbocation

    • one year ago
  56. DLS
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    its about the stability of the carbocation

    • one year ago
  57. abb0t
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    Resonance just tells you where electron behaves or forms a more stable structure

    • one year ago
  58. DLS
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    more resonating structures=more stable C h as 0 resonating structures

    • one year ago
  59. DLS
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    D has one if you see

    • one year ago
  60. abb0t
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    Draw them for acetylene.

    • one year ago
  61. DLS
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    |dw:1360961235810:dw| not sure duh

    • one year ago
  62. abb0t
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    I don't think that would work. Did you move the hydrogen?????

    • one year ago
  63. DLS
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    idk man

    • one year ago
  64. abb0t
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    Resonance is only movement of the electron. Not protons.

    • one year ago
  65. DLS
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    so whatnow

    • one year ago
  66. abb0t
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    Maybe @BluFoot can help right now I'm not on my comp so I can't give detailed answers right now and don't have my notes w/ me. If you're on later I will explain better if no1 else has helped you. I gtg

    • one year ago
  67. DLS
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    hmm okay

    • one year ago
  68. BluFoot
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    A is very stable because of all the resonance from the phenyl groups. B is kinda stable from the resonance of the double bond. This is called an "allylic carbocation" http://science.uvu.edu/ochem/index.php/alphabetical/a-b/allylic-carbocation/ C has no resonance, but it's tertiary at least D is definitely the least stable. Vinylic carbocations (+ on the C=C) are reaalllllllyyyy unstable. The reason is based in orbitals. C=C are sp2, but with a carbocation it becomes sp. sp orbitals are situated close to the nucleus, so the positive charge is very close to the nucleus, which is positive, so it's unstable

    • one year ago
  69. DLS
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    okay,thanks :D

    • one year ago
  70. BluFoot
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    I've never seen the structure in C btw... do you know what it's called?

    • one year ago
  71. DLS
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    ive been taught its bridgehead carbon (out of the plane)

    • one year ago
  72. BluFoot
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    Oh right, I haven't learned about those. It's still probably D but don't make my word for it since I know nothing about the bridges.

    • one year ago
  73. DLS
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    its C idk why....

    • one year ago
  74. BluFoot
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    I have no idea, sorry :/

    • one year ago
  75. abb0t
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    It's a bicyclo compound.

    • one year ago
  76. abb0t
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    Well, "C" would form a radical rather than a carbocation since it's an all hydrocarbon structure. That could be one argument. I'm not entirely sure about this one to be honest. But I can't help but also think the answer could be D since you don't usually ever have primary carbocations. And there's no type of resonance in structure D. If you take out the double bond, you'd have another charge and that would definitely form a very thermodynamically unstable structure. It would definitely prefer to stay.

    • one year ago
  77. aaronq
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    If the answer was to be C, then, i imagine that'd it would be because the strain put on it by it's inability to undergo an sp2 conformation (180 degree angles) since it's fixed on the frame and it would make of high energy/unstable

    • one year ago
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