[taurean]

Could someone explain what would be the product of this reaction? I want to know if we could predict the product before trying out this reaction.

[Rabn]

Products A and D are the same in the proposed possible reaction products.  Consider the basic conditions and alpha carbon vs. beta carbon chemistry.  To help you move in the right direction cosider the pKa/pKb of the K2CO3 and the proposed sites of the addition. Let me know if you need more assistance. 

[taurean]

Products A and D are the same in the proposed possible reaction products.  Consider the basic conditions and alpha carbon vs. beta carbon chemistry.  To help you move in the right direction cosider the pKa/pKb of the K2CO3 and the proposed sites of the addition. Let me know if you need more assistance. 

I changed A and D, my mistake.  Could you explain more clearly, please?

[taurean]

Could someone please explain the question basing on HOMO-LUMO theory?

[Kryolith]

Ok, what we have is two electrophilic centres. The acyclbromide is more electrophilic than the alpha-C of the bromoalkane. So B, D are not very likely. A is an N-acetylation, C a Friedel-Crafts-acylation.
F-C-acylations usually need the presence of a lewis acid as a catalyst (K₂CO₃ is a base), so I would say A is the main product.

[sjb]

Ok, what we have is two electrophilic centres. The acyclbromide is more electrophilic than the alpha-C of the bromoalkane. So B, D are not very likely. A is an N-acetylation, C a Friedel-Crafts-acylation.
F-C-acylations usually need the presence of a lewis acid as a catalyst (K₂CO₃ is a base), so I would say A is the main product.

Out of those given, yes, I'd agree. However, is an amide really more basic than an indole? Seems a tough call between A, and product arising from the indole NH attacking the acyl bromide? Possible cyclisation with the other bromide on to the amide to follow up? How many equivalents of carbonate are you using?

S

[Kryolith]

In recent literature there's always a lewis acid present. Anyway the reaction (and cyclisation) can also take place. (Amides aren't very nucleophilic)

[taurean]

Ok, what we have is two electrophilic centres. The acyclbromide is more electrophilic than the alpha-C of the bromoalkane. So B, D are not very likely. A is an N-acetylation, C a Friedel-Crafts-acylation.
F-C-acylations usually need the presence of a lewis acid as a catalyst (K₂CO₃ is a base), so I would say A is the main product.

Out of those given, yes, I'd agree. However, is an amide really more basic than an indole? Seems a tough call between A, and product arising from the indole NH attacking the acyl bromide? Possible cyclisation with the other bromide on to the amide to follow up? How many equivalents of carbonate are you using?

S

I am using 2 eq's K2CO3.