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chem question help please organic

hi, please could I have some help on question 3aii of this paper. The question asks to draw a dipeptide, on the ms they have drawn the peptide with the COOH group but is it still correct if I drew it with NH2?
Also for part b where it says serotonin reacts with Br2, I understand it reacts with phenol but does it also not react with the alkene via electrophilic addition?
question: https://www.physicsandmathstutor.com/pdf-pages/?pdf=https%3A%2F%2Fpmt.physicsandmathstutor.com%2Fdownload%2FChemistry%2FA-level%2FPast-Papers%2FCAIE%2FPaper-4%2FQP%2FNovember%202017%20(v2)%20QP.pdf
ms: https://www.physicsandmathstutor.com/pdf-pages/?pdf=https%3A%2F%2Fpmt.physicsandmathstutor.com%2Fdownload%2FChemistry%2FA-level%2FPast-Papers%2FCAIE%2FPaper-4%2FMS%2FNovember%202017%20(v2)%20MS.pdf

Thank you!

Reply 1

Original post by anonymous56754
hi, please could I have some help on question 3aii of this paper. The question asks to draw a dipeptide, on the ms they have drawn the peptide with the COOH group but is it still correct if I drew it with NH2?
Also for part b where it says serotonin reacts with Br2, I understand it reacts with phenol but does it also not react with the alkene via electrophilic addition?
question: https://www.physicsandmathstutor.com/pdf-pages/?pdf=https%3A%2F%2Fpmt.physicsandmathstutor.com%2Fdownload%2FChemistry%2FA-level%2FPast-Papers%2FCAIE%2FPaper-4%2FQP%2FNovember%202017%20(v2)%20QP.pdf
ms: https://www.physicsandmathstutor.com/pdf-pages/?pdf=https%3A%2F%2Fpmt.physicsandmathstutor.com%2Fdownload%2FChemistry%2FA-level%2FPast-Papers%2FCAIE%2FPaper-4%2FMS%2FNovember%202017%20(v2)%20MS.pdf
Thank you!

I don’t think there is anything wrong with drawing the peptide bond formed at the NH2 of tryptophan, rather than its carboxylic acid group.

The “alkene” group in the molecule is technically part of something called a pyrrole. In fact the fused rings in tryptophan and serotonin are what we call an indole group in organic chemistry - for reasons not explained at A level (Hückel’s rules), both rings in the indole group are considered aromatic and thus resist electrophilic addition. In theory, the pyrrole part of the molecule should also be susceptible to electrophilic substitution (rather than addition), but the site on the ring that would be most reactive is already bonded to something else (the -CH2CH2NH2).
(edited 2 months ago)

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