More carbonyls wahoo

[dawn parrot]

Attached is the question and the solution

[proud veldt]

<@&1227988359910260737>

Note for OP

+solved @user1 @user2... to close the thread when your doubt is solved. Mention the users who helped you solve the doubt. This will be added to their stats.

[dawn parrot]

how does one infer the second thing here going backwards

following it backwards, i thought it was -OH on top of the 5-ring with a still intact 5-ring

ill draw it hang on

my inference of compound 2

[dawn parrot]

heating -OH makes the double bond go onto the same position as compound number (3) here, goes it not?

[brave kraken]

It does, yeah, but see that there is no methyl group connected to the C-OH, which would be a necessity assuming you prepared the alcohol with an aldehyde and methyl magnesium bromide

Which means that you initially had a tertiary alcohol

Meaning your original compound was a ketone

[dawn parrot]

ah shiyet

that's true

also, why are acidic hydrolysis and conc,H2SO4/heat listed as separate steps?

even in the solution they only consider H+ and heat

[brave kraken]

The hydrolysis is for the magnesium complex to be split into an organic compound and a magnesium salt.

[dawn parrot]

Oh I took that for granted

[brave kraken]

No, it isn't.

[dawn parrot]

?

It sounds correct once you said it

[brave kraken]

Then the second conc.H2SO4 protonates OH and abstracts H2O, generating electrophile (carbocation). No rearrangement since it's already tertiary, so EAS happens

Ortho instead of meta because of bond length constraints.

[dawn parrot]

Yeah got that part

Thanks for solving a lot of my doubts by the way

+solved opt314