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Chem question help please addition polymerisation

Hi, please could I have help on this question, not sure why my answer is wrong.
Question: https://ibb.co/Cs7vN2Sb
Thank you!

Reply 1

Original post
by anonymous56754
Hi, please could I have help on this question, not sure why my answer is wrong.
Question: https://ibb.co/Cs7vN2Sb
Thank you!

I don’t think your answer is wrong.

I suspect there are several acceptable answers to the question, yours being one of them - you could also divide the chain in such a way that you work out the monomers to be but-1-ene and E- or Z-2-chorobut-2-ene, though these answers seem less intuitive to me and I would probably mark them wrong as the “leftover” bits of the segment at the end don’t add up to either monomer used.

I’d need to see the MS, but they’ve probably shown an alternative answer as the expected one and put yours as an acceptable one somewhere in the marking guidance.
(edited 11 months ago)

Reply 2

Original post
by TypicalNerd
I don’t think your answer is wrong.
I suspect there are several acceptable answers to the question, yours being one of them - you could also divide the chain in such a way that you work out the monomers to be but-1-ene and E- or Z-2-chorobut-2-ene, though these answers seem less intuitive to me and I would probably mark them wrong as the “leftover” bits of the segment at the end don’t add up to either monomer used.
I’d need to see the MS, but they’ve probably shown an alternative answer as the expected one and put yours as an acceptable one somewhere in the marking guidance.

Oh yes it does, I didn’t read the markscheme properly, thanks!
I have another question if you wouldn’t mind answering, I’m not sure why h+ isn’t added onto both nitrogen’s in the question below, the ms only accepts if the h+ is added to one nitrogen?
IMG_0911.jpeg

Reply 3

Original post
by anonymous56754
Oh yes it does, I didn’t read the markscheme properly, thanks!
I have another question if you wouldn’t mind answering, I’m not sure why h+ isn’t added onto both nitrogen’s in the question below, the ms only accepts if the h+ is added to one nitrogen?
IMG_0911.jpeg

I imagine it would only protonate the amine and not the pyridine (i.e the benzene ring with a nitrogen replacing one of the C-H’s).

If you understand orbital hybridisation, you’ll be aware that sp^3 hybrid orbitals are of higher energy than sp^2 (because sp^3 orbitals have higher p-orbital character) and so a lone pair in an sp^3 orbital will be more available. The nitrogen in the amine being sp^3 therefore is the more basic.

As for why the pyridine nitrogen isn’t protonated, ideally you want to keep the charge on a species to a minimum and avoid protonating everything. As such, it is usually only the most basic site on the molecule/ion that gets protonated in an acid-base reaction.

Reply 4

Original post
by TypicalNerd
I imagine it would only protonate the amine and not the pyridine (i.e the benzene ring with a nitrogen replacing one of the C-H’s).
If you understand orbital hybridisation, you’ll be aware that sp^3 hybrid orbitals are of higher energy than sp^2 (because sp^3 orbitals have higher p-orbital character) and so a lone pair in an sp^3 orbital will be more available. The nitrogen in the amine being sp^3 therefore is the more basic.
As for why the pyridine nitrogen isn’t protonated, ideally you want to keep the charge on a species to a minimum and avoid protonating everything. As such, it is usually only the most basic site on the molecule/ion that gets protonated in an acid-base reaction.

I see, thanks for the explanation 🙂

Reply 5

Original post
by anonymous56754
Oh yes it does, I didn’t read the markscheme properly, thanks!
I have another question if you wouldn’t mind answering, I’m not sure why h+ isn’t added onto both nitrogen’s in the question below, the ms only accepts if the h+ is added to one nitrogen?
IMG_0911.jpeg

This isn't the friendly of Q and MS combination.

The Q states "two nitrogen atoms, both of which can act as a base", which most students would accept as in invitation to protonate both. Which is what a student doing OCR A would/should do.

The MS simple has the two mono-protonated structures side by side with the word "or" in between.

Importantly, the word "or" is both in lower case and is not emboldened, which I believe means the two answers stated are not the two you must choose from, especially since this is a one-mark Q, they can't be expecting you to know or write half of what TypicalNerd correctly suggested.

I don't mark for CIE, but I have applied in the past, I decided against accepting a contract, due to how dodgy their MSs were.

Reply 6

Original post
by Pigster
This isn't the friendly of Q and MS combination.
The Q states "two nitrogen atoms, both of which can act as a base", which most students would accept as in invitation to protonate both. Which is what a student doing OCR A would/should do.
The MS simple has the two mono-protonated structures side by side with the word "or" in between.
Importantly, the word "or" is both in lower case and is not emboldened, which I believe means the two answers stated are not the two you must choose from, especially since this is a one-mark Q, they can't be expecting you to know or write half of what TypicalNerd correctly suggested.
I don't mark for CIE, but I have applied in the past, I decided against accepting a contract, due to how dodgy their MSs were.

CIE does expect you to know about orbital hybridisation (which imo is unreasonable at this level).

In general, CIE expects more of their students than any of the UK syllabi, so whilst they might not expect a written answer with absolutely everything I have used to explain it, the principles generally should be well understood.

Reply 7

Original post
by Pigster
This isn't the friendly of Q and MS combination.
The Q states "two nitrogen atoms, both of which can act as a base", which most students would accept as in invitation to protonate both. Which is what a student doing OCR A would/should do.
The MS simple has the two mono-protonated structures side by side with the word "or" in between.
Importantly, the word "or" is both in lower case and is not emboldened, which I believe means the two answers stated are not the two you must choose from, especially since this is a one-mark Q, they can't be expecting you to know or write half of what TypicalNerd correctly suggested.
I don't mark for CIE, but I have applied in the past, I decided against accepting a contract, due to how dodgy their MSs were.

Yes, I thought that when it said both nitrogen atoms can act as a base, it is possible to protonate both. I now understand the explanation for it thanks to TypicalNerd but it is definitely something I wouldn’t have thought about in the exam!

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