Shweta Thakur posted an Question
July 10, 2020 • 16:33 pm 30 points
  • IIT JAM
  • Chemistry (CY)

plz expalin this question .... Hs chs , agoh ch 2) heat60 h 3. rans-cyclooctene cis-cyclooctene

Hs CHs , AgOH CH 2) heat NHe H (40%) + (CHa)aN N 3 CHa- NaOH soln. 60 H 3. rans-Cyclooctene Cis-Cyclooctene

2 Answer(s) Answer Now
  • 0 Likes
  • 6 Comments
  • 0 Shares
  • Suman Kumar

    This is Hoffman exhaustive methylation followed by elimination abbreviated as HEME. https://youtu.be/TQ0YYBsIPlA

    eduncle-logo-app

    See the mechanism.

    eduncle-logo-app

    Since cyclooctene can exist in cis & Trans form Hence the product.

    eduncle-logo-app

    If the reactant happens to be cylic ring of less than 8 carbon then only one product i.e cis will be formed. As Trans don't exist

    eduncle-logo-app

    plz draw mam

    eduncle-logo-app

    See

    eduncle-logo-app

    I didn't get

    eduncle-logo-app

    Trans cyclohexene doesn't exist. So only product. But Trans cyclooctene exist so two products

    eduncle-logo-app

    Sweta now?

    eduncle-logo-app

    ok mam

    eduncle-logo-app

    plz tell is it e1cb elimination ....

    eduncle-logo-app

    yes

    eduncle-logo-app

    Whenever there is poor leaving group E1cb occur

    eduncle-logo-app

    mam but n (ch3)3is good leaving group

  • comment-profile-img>
    Dinesh khalmaniya 1

    this is Hoffman exaustive methylation followed by elimination

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

    check the detail explaination

    cropped8840013238379326673.jpg
    eduncle-logo-app

    check it Shweta. hope you will got it

    eduncle-logo-app

    plz draw this on page sir

    eduncle-logo-app

    reaction??

    eduncle-logo-app

    yes

    eduncle-logo-app

    I have sent u the question

    eduncle-logo-app

    yes

    eduncle-logo-app

    plz tell is it e1cb elimanation

    eduncle-logo-app

    E2 elimination

    eduncle-logo-app

    it is good leaving group so gives E2

    eduncle-logo-app

    The E1cB elimination reaction is a type of elimination reaction which occurs under basic conditions, where the hydrogen to be removed is relatively acidic, while the leaving group (such as -OH or -OR) is a relatively poor one. Usually a moderate to strong base is present.

    eduncle-logo-app

    got it??

    eduncle-logo-app

    ok sir

    eduncle-logo-app

    but sir

    eduncle-logo-app

    If it's e2tgen why there is negative charge on carbon and why leaving group is not leaving plz see the structure

  • comment-profile-img>
    Priyanshu kumar

    mixture of cis and trans cyclooctene is obtained from N,N,N trimethylcyclooctylammonium iodide

    eduncle-logo-app

    see what happen actually in this reaction...i think you know this part

    eduncle-logo-app

    this is know sir ...plz solve this question..

    eduncle-logo-app

    yes shweta wait...i m solving...i was busy in some work..sorry for late

    eduncle-logo-app

    it's okay sir

    eduncle-logo-app

    and sir plz tell is it e1cb elimination ???

    eduncle-logo-app

    shweta in e1cb emilination..there is formation of stabilised carbanion

    eduncle-logo-app

    here it is carbanion like transition state...and in e1cb always hoffmann products forms..and in e1 always saytzeff product and in e2 mixed.....i have explained this as due to bulkiness of this group here hoffamnn favours...you have seen this is newmann structure

    eduncle-logo-app

    ok sir

    eduncle-logo-app

    means it is a e1cb

    eduncle-logo-app

    because first proton leave then after leaving group

    eduncle-logo-app

    but sir n(ch3)3is good leaving group then how can this be a e1cb

    eduncle-logo-app

    shweta you have do this mechanism here bulkiness of leaving group comes into play

    eduncle-logo-app

    yes sir

    eduncle-logo-app

    so it's e1cb although good leaving group but bulkiness dominates

    eduncle-logo-app

    yes shweta...

    eduncle-logo-app

    thanku sir

    eduncle-logo-app

    sir but in some books it's written that it's e2 that 's wrong n?

    eduncle-logo-app

    this sir

    eduncle-logo-app

    shweta..see i have written above that in e1cb there is formation of stabilised carbanion but here it is carbanion type transition state formed...and in e1cb hoffmann doninates...and in e2 mixed..so you can say it e2 type in which hoffmann products formed

    eduncle-logo-app

    ok sir 👍👍

  • comment-profile-img>
    Priyanshu kumar best-answer

    shweta this is hoffmann exhaustive methylation reaction....

whatsapp-btn

Do You Want Better RANK in Your Exam?

Start Your Preparations with Eduncle’s FREE Study Material

  • Updated Syllabus, Paper Pattern & Full Exam Details
  • Sample Theory of Most Important Topic
  • Model Test Paper with Detailed Solutions
  • Last 5 Years Question Papers & Answers