[Jonata_B]

Hi guys! Hope you all are staying safe in these strange times.

I'm having a little trouble with these two organic synthesis. Can anyone help me with the steps to prepare these two compounds, from the initial ones? Any organic or inorganic reagents can be used. Thanks!

[Babcock_Hall]

It is a forum rule that you must show your attempt before we can help you, but I will offer a general suggestion.  I often find that it is easier to work backward from the product in a step-by-step manner.

[Synthol]

Hi guys! Hope you all are staying safe in these strange times.

I'm having a little trouble with these two organic synthesis. Can anyone help me with the steps to prepare these two compounds, from the initial ones? Any organic or inorganic reagents can be used. Thanks!

XXX i saw that i cant post this information as soon as i see your attempt I’ll post it

[Jonata_B]

Sorry, I'm new to this forum and didn't know about this rule.
For the first item (b), I thought about first reacting with a strong base (:X), resulting in a negative charge, wich would make the double bond, after Br^- leaving the molecule (E2 mechanism, I think?). But then, I don't know how to proceed to form the second double bond, on the cycle.
For the second item (c), I thought about doing an oxidation with KMNO₄ and heat, but I saw a similar reaction and apparently whens this compound reacts with a double bond, it breaks it in two, generating the carboxilic acid and CO₂? Does that make sense?
Thanks for the *delete me*

[Babcock_Hall]

With respect to c) cold potassium permanganate provides a vicinal diol, which is not what you want.  Under hot, acidic conditions, one obtains more oxidation (the double bond is broken entirely), but which products are formed depend upon which alkene is the starting material.  If the double bond is broken entirely, then your product will necessarily have one less carbon than what you want.  You might try working backwards.

With respect to b), can you think of any transformations that happen to carbon atoms one bond removed from the double bond?  You need to be more specific in your choice of the strong base; depending on which base you use, you may not get the alkene you want as the major product.  Also, the elimination mechanism that you wrote is questionable; the reaction is more likely to happen in one step (E2 elimination) than in two steps (E1cb).

[insertwittyname]

For (B) I was thinking of going as the attached image. The only doubt is if ^tBuOH by virtue of a being a bulky base, prevent Saytzeff dehydrohalogenation and form the desired product? The regioselectivity in the final step just relies on the formation of a conjugated product.

For (C) could we possibly use hydroboration-oxidation to generate a 1° alcohol, and then oxidise that to get the carboxylic acid?

[Babcock_Hall]

We generally ask the OP to do the heavy lifting; however, this is an old thread.

Is your bromine atom in the allylic position?