[a confused chiral girl]

Hi everyone

I have 2 questions which are asking to predict the major products. I have already gave them both a try, and the 2 structures that are drawn in blue are my predicted products. the black ones are what is given.
In #1, I am thinking that only Br gets affected, but should NH also get affected as well? I don't think so..because Br is a much better leaving group. Please correct me if I'm wrong 

In #2, I think an alkane like the one I have drawn is going to be the major product. correct?

thank you everyone!

[a confused chiral girl]

For the second reaction, would equivalents of CH3OH make a difference in the product?  right now, the reageants are CH3OH, H+. I'm not sure if there are going to be 2 OCH3 adding on the carbon, or just one OCH3 and one H..

[Fry]

The second one looks like it will be a transesterification.. you'll end up with a methyl ester.


The first looks good.. I dont know how easily that amine may deprotonate to destroy the grignard though.

[a confused chiral girl]

The second one looks like it will be a transesterification.. you'll end up with a methyl ester.

do you mean this when you say methyl ester? so ...the C is attached to one OCH3 and one OH? instead of 2 OCH3?
thanks~

[Fry]

No, I mean you'll end up with methyl ethanoate..

CH3CO2CH3

[AWK]

Note, in the first reaction a Grignard reagent can react with ortho-ester (at least side product wiil be formed)

[chengyang79]

I think that the Hydrogen atom of the pyrrole ring is an active one, so the grignard reaction can't initiated. and also,grignard reagent may attack the -C(OMe)3 group that is lead to an corresponding dimethylacetal.

The second one ,the reactant be in equilibrium with product.Yield a mixtrue of ethylacetate and methyl-acetate .

[english]

You haven't downloaded that drawing program yet? 

[gtaskiran1977]

The second predict is too strong . 1-Carbonyl groupe =OH+  2-OCH3 attack so -OH and OCH3 connect the same carbon. 3- Second H+ connect -OH group( -OH2+) Its sigma electrons do a = bond and H+(Catalys) to be regenarate. H2C=COCH3OC2H5 (IN MY OPINION, MAY BE?)

[gtaskiran1977]

I think that first reaction very strong. Because pirol is an aromatic compound. And in this structure, Brom is an electron donör in view of mesomerically and resonance form of pyrrole is not suitable on Br-C=. And the other(3. position) is more suitable for this problem. 

[organoman]

I think both reactions are right. Secand one is an example of acid catalysed ketal formation

[AWK]

Second one is an example of acid catalysed ketal formation

The first reagent in this reaction is an ester not a ketone