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Theobromine (C7H8N4O2; M=180.2 g/mol) is an alkaloid found in chocolate. 1)Despite having several nitrogen atoms in...

Theobromine (C7H8N4O2; M=180.2 g/mol) is an alkaloid found in chocolate.

1)Despite having several nitrogen atoms in its sturcture, it is an extremely weak base in water. Provide a reasonable explanation for this behavior?

2)Propose and draw a structural modification to the molecule of theobromine that would transform the substance into a stronger base. Justify your reasoning.

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Answer #1

Any compound having nitrogen atom is basic in nature but it's only the case when the lone pair electrons of nitrogen atom are free for donation.

Here in theobromine lone pairs of nitrogen atoms are involved in the resonance delocalisation and are not free for donation. Therefore the molecule is weakly basic.

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