http://papers.gceguide.com/A%20Levels/Chemistry%20(9701)/9701_w13_qp_43.pdf
http://papers.gceguide.com/A%20Levels/Chemistry%20(9701)/9701_w13_ms_43.pdf
http://papers.gceguide.com/A%20Levels/Chemistry%20(9701)/9701_w13_er.pdf
In Q6 part f(i) , i dont understand 2 things.
First of all, i dont understand why G and H are not similar to
F...if we rotate both the left and right hand side of the molecule,
shouldnt we get F.
Secondly, how does rotating right hand side of J by 60o
clockwise make ot identical to F as suggested by the examiner
report. And why is Chirality of Left hand carbon of both G and H
opposite to that of F.
After all this, how to solve f(iii) ie drawing the fourth
optical isomers.
Is this related to R,S configurations or is this something
else...as to where can i read more about this?
If you could explain this i detail, i would be
grateful..thanks.
This is the toughest question in the paper for 2 reasons : because
it's slightly beyond the A level syllabus, and also because it's
extremely difficult to visualize (solely using imagination) the
rotation of 3D structures.
Going beyond the syllabus, ie. at Uni level, the correct way to
approach such questions is to assign priorities to the 4 different
groups based on the
Cahn–Ingold–Prelog priority rules, and concordantly label each
of the 2 chiral C atoms present as either
R (Rectus) or S (Sinister). The 4 optical stereoisomers would
then be (2R,3R), (2R,3S), (2S,3R) and (2S,3S), where (2R,3R) &
(2S,3S), and (2R,3S) & (2S,3R), are the 2 sets of enantiomers, while
(2R,3R) & (2S,3R), (2R,3R) & (2R,3S), (2S,3S) &
(2S,3R), and (2S,3S) & (2R,3S), are the 4 sets of diastereomers.
Alternatively, or simultaneously, if you can obtain (or make for
yourself) a 3D 'ball-&-stick' model of the molecule, and rotate
each end, it'll help you to better visualize and solve this
question. Of course, you won't be allowed to bring in such tools or
toys in the A level exams, so you'll have to settle with using your
hands : orientate your fingers (using both hands) in a tetrahedral
geometry, with 1 finger towards you (the wedge), 1 finger away from
you (the hash or dash), and 2 fingers (1 from each hand) neither
towards or away (the normal bonds), then slowly rotate your hands.
While simultaneously mentally keeping track of which finger
representing which group of atoms, *and* the priority of each group
(if you're assigning R vs S configuration to help you answer this
question). Not an easy task, unfortunately.
You could say this question is unfair to be asked at A levels.
But it's a bell-curve anyway, so since it's unfair for everyone,
it's arguably still fair. Such questions are intended for only the
top few % of the A level cohort to be able to answer correctly,
otherwise too many people would score A grade. Regardless of where
you're ranked in the cohort, exam-smart students would always skip
such time-consuming questions first, complete the rest of the
paper, then go back to such 'skipped' questions last. It'll be
penny-wise-pound-foolish to waste 15 min struggling on this 3 marks
question, then find out at the end of the exam that you only have 3
min left with 15 marks of much easier questions left
unanswered.
Lets assume that i know how to assign R and S priorities
To assign these, the lowest priority group has to be oriented
away from us..in this case, the lowest priority group is the
Hydrogen atom but the problem is that on the Left Hand Carbon atom
for each of the structures, the H-atom is shown to lie on the plane
rather than pointing out or into the plane...so assuming that we
know how to assign R and S, how can we get past this issue?
By visualizing the structure vividly in 3D space using your
imagination, than slowly rotating (not just the single sigma bond,
but move the entire structure) it in your mind, until the lowest
priority substituent, is pointing away from yourself. And try using
your fingers (orientated in a tetrahedral geometry, eg. left hand 3
fingers in a trigonal pyramidal tripod stand, right hand's
forefinger representing lowest priority facing up, before rotating
it till it's away from you) to help.
Also see these videos :
https://www.youtube.com/watch?v=auphHXYK8tE
https://www.youtube.com/watch?v=kFD6hzLseVs