[a confused chiral girl]

Hello~

I am unsure what reagents to use that can form the products for these 2 questions. I tried to give it a couple of attempts, and this is what I have ended up with.
I'm not sure if they make sense, especially for the second one because the product has a protecting group..

for #1, I don't know what to use to kick off the C=0Cl group..
thanks!

[a confused chiral girl]

The Second One....#2

thank u 

[Dan]

#1 You could have a look at decarboxylation
#2 Careful, can you draw a mechanism for that second step? Think about the oxidation state of the C in the carboxylic acid group compared to the acetal group in the product.

[kremar]

on #1, the two carbonyls beta to each other make the hydrogen alfa to both much more acidic than the two other alfa hydrogens. there's no need to protect the ketone.

the acyl chloride group is pointless, since you dont want to use that carbonyl as a nucleophillic center.
beta-keto acids and beta-keto esters, however, can be decarboxilated easily to yield ketones...

[a confused chiral girl]

#1 You could have a look at decarboxylation
#2 Careful, can you draw a mechanism for that second step? Think about the oxidation state of the C in the carboxylic acid group compared to the acetal group in the product.

#1 I looked at decarboxylation and realized how ridiculous my attempt was. Thanks for the pointer. I changed it now...but will adding H3O+, and heat give me the product directly?
#2. I still know that OHCH2CH2OH, H+ gives a acetal/ketal protecting group..and the end product does indeed have a protecting group..hm...