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Archived Discussion => 2010 => Mid-year exams => Exam Discussion => Victoria => Chemistry => Topic started by: ashwin on June 10, 2010, 01:13:30 am

Title: Equivalent Proton question
Post by: ashwin on June 10, 2010, 01:13:30 am
In the NMR Question, it asked: "The signal at 1.3ppm is split into a triplet. What is the number of equivalent protons bonded to the adjacent carbon atom?"

I put 0, as the protons bonded to the adjacent carbon atom are non-equivalent (different from the CH2 protons), so none are equivalent (in the same environment).
However, Mao's answer says 2. Can anyone clarify this please? (Question 2 d i).

Thanks
Title: Re: Equivalent Proton question
Post by: vexx on June 10, 2010, 01:19:14 am
yeah adjacent carbon atom, the number of hydrogens, therefore it is a triplet caused by 2 hydrogen atoms.
its definitely 2.
Title: Re: Equivalent Proton question
Post by: Davoo! on June 10, 2010, 08:24:30 am
I got 2. I think it's the N+1 rule?
Title: Re: Equivalent Proton question
Post by: vexx on June 10, 2010, 02:56:53 pm
I got 2. I think it's the N+1 rule?

yep that's it.
Title: Re: Equivalent Proton question
Post by: nick5335 on June 10, 2010, 04:21:22 pm
yea... i got 0 as well, im 100% sure this is the answer... one of the trick Q's
Title: Re: Equivalent Proton question
Post by: monicapham93 on June 10, 2010, 05:13:53 pm
yeah ive been stressing about this too... i put 0... cause they weren't equivalent.. and kinda did this whole explanation thing underlining the word EQUIVALENT.

yet most people didnt pick up on this.

am i completley off?
Title: Re: Equivalent Proton question
Post by: Greggler on June 10, 2010, 05:19:09 pm
if this is another ghey friggin vcaa trick ill be pisseeeddd

fuckn hell. dont know whether everyone's overthinking it or what. but this exam has just turned out to be the biggest bitch. I studied so much for it and if it ends up ive lost majority of my marks on stupid crap like this it'll piss me off. What'll piss me even more off is if i end up doing better for physics (which it looks like might be the case) when i did not study for physics and a absolute shitload for chem.

rawwwwwrrrrrrrrrrr
Title: Re: Equivalent Proton question
Post by: jimmy999 on June 10, 2010, 06:39:42 pm
The answer is definitely 2. It's not a trick question at all. Or even so, if the protons aren't equivalent at all, then this would be too difficult of a question for year 12s to answer
Title: Re: Equivalent Proton question
Post by: kakar0t on June 10, 2010, 06:41:51 pm
Hahaha if VCAA embedded some sort of trick in this question i've lost all faith in the system IMO :/
Title: Re: Equivalent Proton question
Post by: amimery on June 10, 2010, 09:11:56 pm
 its deceiving that question
 because it previously states says
" the signal is split into a triplet"
 why would they tell you that in the first place?
is it possibly an error on vcaas part?
Title: Re: Equivalent Proton question
Post by: kenhung123 on June 10, 2010, 09:24:43 pm
It most likely you are not used to the chemistry wording of it. Its saying how many hydrogens in the same chemical environment adjacent to the hydrogen under investigation causes a triplet in NMR spectrum
Title: Re: Equivalent Proton question
Post by: chem-nerd on June 10, 2010, 09:42:24 pm
It most likely you are not used to the chemistry wording of it. Its saying how many hydrogens in the same chemical environment adjacent to the hydrogen under investigation causes a triplet in NMR spectrum
^^this
Title: Re: Equivalent Proton question
Post by: VeryCrazyEdu. on June 10, 2010, 09:47:55 pm
I took the question as asking how many protons on the adjacent carbon were equivalent...as in off that carbon...how many were in the same environment lol
Title: Re: Equivalent Proton question
Post by: Lighties on June 10, 2010, 09:53:03 pm
I debated over this question and in the end put a 0 with an explanation, and squished into whatever space was left another explanation stating that if it wasn't the case, then it's 2. Except I wrote 2 at the end really small, so I'm not sure if the examiners'll be bothered reading it. =|

I'm going to hope they mark both as right though =|
Title: Re: Equivalent Proton question
Post by: VeryCrazyEdu. on June 10, 2010, 10:00:23 pm
yeah...using the n+1 rule...the question said equivalent protons on the adjacent carbon so i kinda assumed how many protons attached to that carbon are equivalent...which is 2 obvioucly because they dont split each other....kinda looking silly now because...why wouldn't they be equivalent lol *prays the answer is 2
Title: Re: Equivalent Proton question
Post by: Lighties on June 10, 2010, 10:15:34 pm
Yeah, I was trying to decide which definition of 'equivalent' they meant. XD Both answers looked dodgey either way, so I just picked one and hoped for the best. :P
Title: Re: Equivalent Proton question
Post by: Mao on June 10, 2010, 10:38:14 pm
The answer is definitely 2. The exact wording reads:

"What is the number of equivalent protons bonded to the adjacent carbon atom?"

"equivalent proton" here refers to protons that are the same environment compared to each other. It is well established that the adjacent carbon atom is bonded to two H, and these two H are in the same, thus there are two equivalent protons bonded to the adjacent carbon.

If you have interpreted it the other way, the question would have read:

"What is the number of protons bonded to the adjacent carbon atom that are equivalent to the protons detected at ppm?"
This question doesn't make logical sense. If the answer is more than 0, i.e. the carbon and H environments are equivalent, all of these protons will be found in the same peak at 1.3ppm, thus it will be referring to the adjacent carbon atom that is of a different environment. Hence the answer has to be 0, and the interpretation goes 'how many other protons outside of this peak is equivalent to this peak? 0 under all circumstances'.
Title: Re: Equivalent Proton question
Post by: Lighties on June 10, 2010, 11:02:33 pm
The answer is definitely 2. The exact wording reads:

"What is the number of equivalent protons bonded to the adjacent carbon atom?"

"equivalent proton" here refers to protons that are the same environment compared to each other. It is well established that the adjacent carbon atom is bonded to two H, and these two H are in the same, thus there are two equivalent protons bonded to the adjacent carbon.

If you have interpreted it the other way, the question would have read:

"What is the number of protons bonded to the adjacent carbon atom that are equivalent to the protons detected at ppm?"
This question doesn't make logical sense. If the answer is more than 0, i.e. the carbon and H environments are equivalent, all of these protons will be found in the same peak at 1.3ppm, thus it will be referring to the adjacent carbon atom that is of a different environment. Hence the answer has to be 0, and the interpretation goes 'how many other protons outside of this peak is equivalent to this peak? 0 under all circumstances'.

That's some pretty good logic, but isn't 0 technically a correct answer? And why did they even include the word 'equivalent'?
Title: Re: Equivalent Proton question
Post by: crayolé on June 10, 2010, 11:04:18 pm
equivalent refers to the 2 H's that are equivalent on the adjacent carbon
It's just sucky english that goes both ways
Title: Re: Equivalent Proton question
Post by: Mao on June 10, 2010, 11:07:02 pm
"Equivalent protons" is a fairly common phrase in NMR, it usually refers to a group protons bonded to the same carbon [or carbons of the same environment]. Since these protons [bonded to the same carbon] are in the same environment, they are equivalent to each other, thus as a group, they are called "equivalent protons".

So as opposed to saying "it has a neighbouring -CH2- group", you can say "there are two neighbouring equivalent protons".
Title: Re: Equivalent Proton question
Post by: Lighties on June 10, 2010, 11:11:55 pm
I see, thank you!

Sigh, my explanation is completely wrong, there goes another mark. >.>

Urgh at sucky english/not enough knowledge for chem.
Title: Re: Equivalent Proton question
Post by: Davoo! on June 10, 2010, 11:17:43 pm
if this is another ghey friggin vcaa trick ill be pisseeeddd

fuckn hell. dont know whether everyone's overthinking it or what. but this exam has just turned out to be the biggest bitch. I studied so much for it and if it ends up ive lost majority of my marks on stupid crap like this it'll piss me off. What'll piss me even more off is if i end up doing better for physics (which it looks like might be the case) when i did not study for physics and a absolute shitload for chem.

rawwwwwrrrrrrrrrrr

I feel your pain.
Physics 6 exams, and I feel really confident.
Chemistry 17 exams, and I'm so sure I got analed by their 4375643979836753 booby traps.
Title: Re: Equivalent Proton question
Post by: clumsy_culhane on June 12, 2010, 08:31:23 pm
The answer is definitely 2. The exact wording reads:

"What is the number of equivalent protons bonded to the adjacent carbon atom?"

"equivalent proton" here refers to protons that are the same environment compared to each other. It is well established that the adjacent carbon atom is bonded to two H, and these two H are in the same, thus there are two equivalent protons bonded to the adjacent carbon.


Thanks for the clear-up Mao. I put down 0 as well, as I thought as per a few practice exams, that splits have to be formed from non-equivalent protons. Maybe they will give marks for both 0 and 2, as it's somewhat ambiguous?  Far out.. this makes me annoyed, they put that equivalent word in there, and a lot of the people that really thought about the question then got it wrong :(


Edit: From KBT solutions :"If the hydrogens of a particular environment have n neighbouring, non-equivalent hydrogens,
the peak from that environment will be split into n+1 component peaks.
Keep in mind that the word ‘neighbouring’ as it’s used above means ‘on the adjacent carbon
atom’. ‘Non-equivalent’ means ‘not of the same environment’."

And yes, I know I'm now wrong as proven by Mao in all his awesomeness, but I still want to feel a little right...
(http://www.kbtlectures.com/wp-content/uploads/2010/04/KBT_unit3chemistry_trialexamsolutions.pdf)
Title: Re: Equivalent Proton question
Post by: sajib_mostofa on June 30, 2010, 02:44:46 pm
I'm pretty sure the answer is 0. Equivalent protons are protons in the same environment but in the structure, the protons are all in different environments. Hence it is 0.
Title: Re: Equivalent Proton question
Post by: kenhung123 on June 30, 2010, 02:58:11 pm
Pretty sure they are talking about protons that are equivalent and adjacent to the ones in question. Sure, they are non equivalent with respect to the hydrogen in question, however they are equivalent to one another in the adjacent environment. By definition in the n+1 rule, n=number of equivalent protons.
Title: Re: Equivalent Proton question
Post by: sajib_mostofa on June 30, 2010, 03:29:26 pm
Sounds a bit ambiguous to me...
Title: Re: Equivalent Proton question
Post by: pooshwaltzer on June 30, 2010, 07:23:22 pm
It most likely you are not used to the chemistry wording of it. Its saying how many hydrogens in the same chemical environment adjacent to the hydrogen under investigation causes a triplet in NMR spectrum

Guys,

Even though the answer is 2, it would be probable to attract consequential/consolation marks IF adequate explanation was provided to substantiate the albeit flawed construction of the facts surrounding the question. So if your explanatory paragraph provides logical and rational justification of the answer 0, despite it being a misinterpretation of the question, then SOME marks will be awarded for commensurate effort with due regard and consideration.
Title: Re: Equivalent Proton question
Post by: kenhung123 on June 30, 2010, 10:26:18 pm
Its only worth 1 mark from memory.
Title: Re: Equivalent Proton question
Post by: m@tty on June 30, 2010, 11:58:08 pm
Yep, 1 mark.

And honestly I think that 0 has no chance of getting the mark; even though on reading it is ambiguous, that wording is prevalent when dealing with these type of questions.
Title: Re: Equivalent Proton question
Post by: iffets12345 on July 01, 2010, 12:12:38 am
Crap I do not know what I put for that one! Now I'm all worried!

Is the debate as to what equivalent proton means?
e.g:

Side A believes equivalent proton means protons similar to the Ch3 environment.
Side B states equivalent protons are just Hs on the adjacent carbon which are esentially in the same environment.

I HOPE I WROTE TWO FREAKING HELL.
Title: Re: Equivalent Proton question
Post by: chansthename on July 01, 2010, 12:01:40 pm
^^ Calm down, I'm sure you did great