The Student Room Group

Protonation question

Hi,

I was wondering if someone could let me know why it is the O that gets protonated instead of a C? Thanks in advance!!#

Q2H in https://www.c3l6.caths.cam.ac.uk/files/C3L6_student_exam_2015.pdf
Ans: https://www.c3l6.caths.cam.ac.uk/files/C3L6_Teachers_mark_scheme_2015.pdf
Original post by Felix'sfreckles
Hi,

I was wondering if someone could let me know why it is the O that gets protonated instead of a C? Thanks in advance!!#

Q2H in https://www.c3l6.caths.cam.ac.uk/files/C3L6_student_exam_2015.pdf
Ans: https://www.c3l6.caths.cam.ac.uk/files/C3L6_Teachers_mark_scheme_2015.pdf


Oxygen has a lone pair of electrons and is electronegative.
Original post by charco
Oxygen has a lone pair of electrons and is electronegative.


Thank you!! I wasn't sure if an element being more electronegative in general meant it accepted a hydrogen more readily...
Original post by Felix'sfreckles
Thank you!! I wasn't sure if an element being more electronegative in general meant it accepted a hydrogen more readily...


The lone pair of electrons is the most important factor.
Original post by charco
The lone pair of electrons is the most important factor.


Ah okay thanks! If there was also a NH2 group, then would the O still be the one that is protonated because though both N and O have lone pairs, O has a bigger electronegativity?
Original post by Felix'sfreckles
Ah okay thanks! If there was also a NH2 group, then would the O still be the one that is protonated because though both N and O have lone pairs, O has a bigger electronegativity?


They will both be protonated
Original post by charco
They will both be protonated


Ah okay, thank you!!

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