[boramhuh]

Hello all,

I had a quick question.

As mentioned, 3-cyclohexen-1-carboxylic acid goes through reactions in 2 steps.
First reaction is with
 I2, Sodium bicarbonate in CH3CN-water

then this product reacts with
Sodium Hydroxid in MeOH-water

What would be the product?

I assume in the first step, you would halogenate the double bond in Cyclohexene and bicarbonate binds to the other of the doulbe bond?
-This i'm not quite sure, because I learned that Iodine doesn't really react with double bonds... and since bicarbonate is a weak base, wouldn't it compete with Iodine to act as a nucleophile to attach to the other side of the double bond?


And for the second step, I guess the carboxylic acid group would be attacked through
acid catalyzed mechanism to form an ester with methoxy group?...

Hmm.. I'm confused.

please help me out

Thank you!

[discodermolide]

Hello all,

I had a quick question.

As mentioned, 3-cyclohexen-1-carboxylic acid goes through reactions in 2 steps.
First reaction is with
 I2, Sodium bicarbonate in CH3CN-water

then this product reacts with
Sodium Hydroxid in MeOH-water

What would be the product?

I assume in the first step, you would halogenate the double bond in Cyclohexene and bicarbonate binds to the other of the doulbe bond?
-This i'm not quite sure, because I learned that Iodine doesn't really react with double bonds... and since bicarbonate is a weak base, wouldn't it compete with Iodine to act as a nucleophile to attach to the other side of the double bond?


And for the second step, I guess the carboxylic acid group would be attacked through
acid catalyzed mechanism to form an ester with methoxy group?...

Hmm.. I'm confused.

please help me out

Thank you!

I2 certainly reacts with the C=C bond, what else does the bicarbonate do?
NaOH-Methanol are not esterification conditions for a carboxylic acid, this mixture is basic not acidic.

[nox]

You have a carboxylic acid, what would bicarbonate do?

[boramhuh]

You have a carboxylic acid, what would bicarbonate do?

wouldn't it act as a base and deprotonate H in the hydroxy group?...
then... the alkoxy group itself would act as a base and attack... methanol? since it's an acid? ...gahhh.

[nox]

The first step is iodination of the double bond, HOWEVER there is more than one nucleophile that can intercept the iodonium intermediate.