15-06-10 Simple Organic : Heat Em Up

17 Answers

1
Sonne ·

its a very close call in deciding which has more migratory aptituide
ethyl or methyl

but u can see there are two methyl groups in comparision two one ethyl group
when there is closesness in migratory aptituide
we go for major product
so the methyl group migrating will be the major product (as it has greater chance)

correct me if i am wrong !

1
Ankur ·

for #18
first edited.. then you posted. :P

39
Pritish Chakraborty ·

@Post #15, you have misinterpreted my statement about beta-keto acids. Nobody asked you to look at the ketone group which is formed by hydrolysis of the acetal.
There is no such thing in Morrison and Boyd. Blanc's rule for the heating of 1,3-dicarboxylic acids states that the loss of CO2 occurs, and occurs by a cyclic transition state(sounds familiar?).

But good that you understood...and later edited :P

39
Pritish Chakraborty ·

Not rearrangement actually..migration I mean. And that's CH2CH3

1
Ankur ·

For Q1:

--Edited--

1
Ankur ·

For Q2:

err... entire courtesy to Pritish Chakraborty (including images).

PS: @Pritish: I was not being adamant. I was just trying to check out my basics and get them correct in case they were wrong. :P

39
Pritish Chakraborty ·

@going ahead : I could explain everything right now, but Ankur's being adamant and wants to explain himself first..he's having lunch. Let His Majesty finish his royal luncheon and then I'll see..haha.

1
souvik seal ·

ankur post the mechanism please

1
Ankur ·

Q2

1
souvik seal ·

2nd

39
Pritish Chakraborty ·

The mechanism is perfect....but you have not taken into account migratory aptitude!

1
Sonne ·

39
Pritish Chakraborty ·

Yes it is indeed by the cumene hydroperoxide method. You're nearly there.

Just to clarify, in Q1, those are ether groups attached on the left side of cyclohexane, not carbonyls.

1
Sonne ·

and an alcohol

my working is simillar to production of phenol by cumene peroxide method

yes i think some ammendment is required

please wait

39
Pritish Chakraborty ·

Show your working in Q3 bhai...you are nearly there if you're following the right line of thinking. There will be two products however.

1
Sonne ·

3
??

39
Pritish Chakraborty ·

Incorrect answer, but nice try souvik!
A little hint for you. The cyclopropane group is extremely acid labile. It may look like pinacol rearrangement, but it's not.

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