PREFERENTIAL OZONOLYSIS

well, today seems to b organic DAY!!! [4]

so try this one : ans is "A"

pl justify!!!

21 Answers

21
tapanmast Vora ·

[11] [11][11][11][11][11][11][11][11]

that means ans A is correct and the mechanism in MTG publication has some flaw (mayb) (SORRY TO MR. MUKUL RAY)............

is 'sykes' quite a dependable source Sir?

3
msp ·

kkk sir

62
Lokesh Verma ·

@sankara.. there is equal steric hindrance at both the sites..

infact more on the right one..

62
Lokesh Verma ·

Yes I think so because the rate determining step is this attack..

But I am not absolutely sure on this one.

3
msp ·

i included steric hinderance so i will dot the option A

21
tapanmast Vora ·

OH K K.... THEN I BETTER BELIEVE that its O+ which attacks and not O-

thnx for the wonderful reference!!!

3
msp ·

can steric effects affects the formation of ozonide in this rxn sir.

33
Abhishek Priyam ·

okieee

62
Lokesh Verma ·

@priyam, sky it is the O+ attacking...

See peter sykes' thing that i posted.. It writes that the part of ozone which is electrophilic initiates the attack. So O+ is the one that attacks.

I have no doubt on peter sykes. That is one of the best books on mechanism that is available.

1
skygirl ·

nahi ... double jake attacj karta hai ... O pe...

was telling naa priyam.... [saw sir's notes]

33
Abhishek Priyam ·

mechanism as in : "Name Reactions" by Mukul C Ray

but in this O- is attacking... [7]

33
Abhishek Priyam ·

it has to be (a) or (b)...
so theres 50-50 chance.. take it... make a tukka... [3]

62
Lokesh Verma ·

From the above it is clear that the +ve charge of ozone will attack first..

so it will attack a electron rich center.....

1
vector ·

+m is acting on both is distance independent but -i is distance dependent n more on right one.so right one more electrophilic thus my ans is correct.

62
Lokesh Verma ·

Reference from Sykes.

21
tapanmast Vora ·

mechanism as in : "Name Reactions" by Mukul C Ray

this mite aid........

but it actually contrasts the answer..........

1
rohan poddar ·

well that is exactly wat i pointed nishant bhaiya ....

33
Abhishek Priyam ·

electron rich bond or deficient bond will be attacked.. [7]

62
Lokesh Verma ·

@ priyam.. yes ur tukka is half correct..

only we have to decide which in a or b

bcos we have to see which one Ozone will attack first..

I think the "left" double bond because there is +R effect on the right one..

I think it should be b :)

1
rohan poddar ·

well i think it shuld be (b) because O-CH3 is involved in resonance with the double bond.

I dunno i myt be wrong.

1
vector ·

as we know dat 2moles of o3 ll be reqd for complete oxidation but we r given 1 mole so more electrophilic bond ll be attacked n it s d right one
if u need further explaination tell me i llexplain it

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