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DLS

  • 2 years ago

Organic chemistry

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

  2. shubhamsrg
    • 2 years ago
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    D) maybe ?

  3. shubhamsrg
    • 2 years ago
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    A) is 3 degree and so is C)

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

  5. DLS
    • 2 years ago
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    its definitely not A for sure

  6. DLS
    • 2 years ago
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    C is not 3 degree i guess

  7. shubhamsrg
    • 2 years ago
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    C is attached to 3 carbons ?

  8. DLS
    • 2 years ago
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    its bridgehead

  9. shubhamsrg
    • 2 years ago
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    hmm ? well still there are 3 carbons !

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

  11. DLS
    • 2 years ago
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    ITS C DAMMIT

  12. shubhamsrg
    • 2 years ago
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    hmm,, sorry about that then! :|

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

  14. DLS
    • 2 years ago
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    hmm okay sorry :P

  15. shubhamsrg
    • 2 years ago
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    Wish your thinking was true!

  16. shubhamsrg
    • 2 years ago
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    Well I have never seen a bridged carbocation before.

  17. DLS
    • 2 years ago
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    are u freaking kidding me ._.

  18. shubhamsrg
    • 2 years ago
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    On a bridge head a positive carbon never occurs ~Wikipedia

  19. shubhamsrg
    • 2 years ago
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    http://en.wikibooks.org/wiki/Organic_Chemistry/Introduction_to_reactions/Carbocations

  20. DLS
    • 2 years ago
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    so what :P

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

  22. DLS
    • 2 years ago
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    wtf

  23. shubhamsrg
    • 2 years ago
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    :)

  24. DLS
    • 2 years ago
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    whaaaaaaaaaaat

  25. DLS
    • 2 years ago
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    thoda detail zara?

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

  27. shubhamsrg
    • 2 years ago
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    never formed*

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

  29. DLS
    • 2 years ago
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    formed*

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

  31. shubhamsrg
    • 2 years ago
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    reason of the fact*

  32. DLS
    • 2 years ago
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    \m/

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

  34. DLS
    • 2 years ago
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    god i cant read that whole thing :/

  35. shubhamsrg
    • 2 years ago
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    learn as fact! thats what I just did !

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

  37. DLS
    • 2 years ago
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    rehne de be :P

  38. shubhamsrg
    • 2 years ago
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    sure! :D

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

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

  41. Yahoo!
    • 2 years ago
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    Shuld nt the answer be D............

  42. chmvijay
    • 2 years ago
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    i think answer is D

  43. DLS
    • 2 years ago
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    its C

  44. DLS
    • 2 years ago
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    and its proven I guess

  45. DLS
    • 2 years ago
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    @abb0t

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

  47. DLS
    • 2 years ago
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    answer is C?

  48. DLS
    • 2 years ago
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    wikipedia says too..

  49. DLS
    • 2 years ago
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    but i want smt more detailed

  50. abb0t
    • 2 years ago
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    Wikipedia says the answer is C?

  51. DLS
    • 2 years ago
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    On a bridge head a positive carbon never occurs ~Wikipedia

  52. abb0t
    • 2 years ago
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    The + isn't on the bridge though.

  53. DLS
    • 2 years ago
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    that is why it cant resonate,the charge is localized.

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

  55. abb0t
    • 2 years ago
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    Resonance is not the same as formation of a carbocation

  56. DLS
    • 2 years ago
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    its about the stability of the carbocation

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

  58. DLS
    • 2 years ago
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    more resonating structures=more stable C h as 0 resonating structures

  59. DLS
    • 2 years ago
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    D has one if you see

  60. abb0t
    • 2 years ago
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    Draw them for acetylene.

  61. DLS
    • 2 years ago
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    |dw:1360961235810:dw| not sure duh

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

  63. DLS
    • 2 years ago
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    idk man

  64. abb0t
    • 2 years ago
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    Resonance is only movement of the electron. Not protons.

  65. DLS
    • 2 years ago
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    so whatnow

  66. abb0t
    • 2 years ago
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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

  67. DLS
    • 2 years ago
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    hmm okay

  68. BluFoot
    • 2 years ago
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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

  69. DLS
    • 2 years ago
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    okay,thanks :D

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

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

  72. BluFoot
    • 2 years ago
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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.

  73. DLS
    • 2 years ago
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    its C idk why....

  74. BluFoot
    • 2 years ago
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    I have no idea, sorry :/

  75. abb0t
    • 2 years ago
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    It's a bicyclo compound.

  76. abb0t
    • 2 years ago
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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.

  77. aaronq
    • 2 years ago
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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

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