Simun Mishra posted an Question
July 29, 2020 β€’ 16:28 pm 30 points
  • IIT JAM
  • Chemistry (CY)

Why in case of pinacol pinacolone rearrangement mechanism when c+ form in stable position why bond sifting occurs ?

2 Answer(s) Answer Now
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  • comment-profile-img>
    Dinesh khalmaniya 1

    hope this will help you

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    sir in my book also their is no reaction given like this which product is aldehyde

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    later I'll check if some examples given in my books

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    ok sir tq sir

  • Suman Kumar best-answer

    See carbocation rearrange only if there is formation of more stable carbocation. Once carbocation is formed in pinacol then after rearrangement more stable carbocation is formed.

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    I will clear your doubts for sure.

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    just you respond and my answer

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    Now you tell me which carbocation is more stable

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    3degree

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    the 2nd one

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    Correct. now rearrangement will only be possible if there is formation of more stable carbocation

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    Now you tell me is rearrangement is possible

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    please respond other wise your doubts will remain forever

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    i will help you dear. please respond

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    See this.

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    Answer to your previous question which Dinesh answered incorrectly.

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    but sir aldehyde can't form na

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    it always gives ketones

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    why not ?

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    That's why mechanism is important

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    I m checking it sir

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    I wanted to correct you step by step but you were not responding so i answered it completely

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    but sir in 2nd steep why H migrate to carbocation

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    Is there any other possibility Simun

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    I can't understand

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    See once again I am saying carbocation rearrange tabhi hoga jab stable carbocation banega. Here mesomeric carbocation ban raha hai.

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    see this

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    ok sir

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    but sir in books and is ketone of the reaction

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    i didn't get

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    ans of the question means the product of the reaction is ketone .?

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    in books

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    Product is definitely aldehyde. please trust me

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    but sir in books in ketone so I asked

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    For this if product is Ketone then it is definitely wrong

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    ok ..sir

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    Please mechanism isiliye important hota hai.

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    yes sir I will do mechanism

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    https://youtu.be/5Ujj265D0HU

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    See this Simun 😊

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    i have seen this sir

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    Then you must have listened that mesomeric carbocation don't undergo for rearrangement

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    yes

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    Then you can solve the problem.

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    yes except this question

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    No Simun don't think this is exception. Go by mechanism. you will not do mistake

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    Solve this & so your product

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    ok sir

  • comment-profile-img>
    Dinesh khalmaniya 1 Best Answer

    in the pinacole pinacolone rearrangement carbocation is formed so rearrangement possible

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    here we will see the migratory aptitude of groups

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    if possible the ring expansion takes place

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    but sir we will remove OH to from stable c+ na so why next rearrangment takes place

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    next rearrangement to get most stable carbocation

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    we rearranged the carbanion untill we can't get most stable carbocation

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    sir in this case the carbocation is 3 degree so why further the rearrangment or shifting of CH3 occurs

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    wait I'm explaing this

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    check this

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    always remember stability order of carbocation which we have discussed in previous query 😊

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    got it Simun??😊😊

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    yes sir ...if stable then it is possible na

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    yes, we have to make most stable carbocation. in pinacole pinacolone rearrangement substituted carbocation is formed so we shift group

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    now understood concept?

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    Simun check this rearrangement notes, this will help you to understand concepta

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    yes sir I got it but sir pls check the comment of suman sir he told that aldehyde also form in some case

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    wait..

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    ok sir

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    this was the question you've sent yesterday 😊

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    yes sir

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    so I m confused on that question sir 2 mechanism are come for this so

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    Simun you can my solution it is always based on comcepts and reference source so i always provide references also

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    I know sir and I have done this

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    πŸ˜ŠπŸ‘

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    but after seeing this I m confused so I asked

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    yes sir he told ring expansion Hoga hi nahi tho ..I m confused

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    yes sir I m also confuse on that because my product is ketone

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