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junior college 1 | H3 Maths
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My answer will be Compound A. However i am not sure if Compound B will be the correct answer instead?
Date Posted: 3 years ago
Views: 588
B. The nucleophile attacks from the opposite side of the leaving group.
There is an inversion of configuration.
There is an inversion of configuration.
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg)/09%3A_Phosphate_Transfer_Reactions/9.03%3A_Phosphate_Transfer_Reactions_-_An_Overview
Refer to the energy diagram for the pentavalent transition state
Refer to the energy diagram for the pentavalent transition state
Thank you! Actually i have another question. Could u please help me if i post it under answers?
Got to see the question first
I added the question together with my answer. My approach to the question is stated in the answers but not too sure if my way of thinking is correct?
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Is my concept correct here? Ketone is meta directing hence is 1,3. So i count from the carbon nearest to ketone (the circled carbon) to the third carbon. There can be two possibilities. However the one on top cannot be the answer due to steric hindrance. Am i correct?
Date Posted:
3 years ago
Both are possible.
The ketone attached to C1 is meta-directing (1,3 relative to this carbon)
The alkyl group next to it on C2 is ortho-para directing (2,4 relative to this carbon)
Both directing groups are in sync and don't conflict. So you'll expect the SO3H to be added to be added to C3 or C5.
The steric hindrance just means that addition to C3 will be the minor product and to C5 will be the major product. (In some percentages)
It isn't necessarily all or nothing.
The ketone attached to C1 is meta-directing (1,3 relative to this carbon)
The alkyl group next to it on C2 is ortho-para directing (2,4 relative to this carbon)
Both directing groups are in sync and don't conflict. So you'll expect the SO3H to be added to be added to C3 or C5.
The steric hindrance just means that addition to C3 will be the minor product and to C5 will be the major product. (In some percentages)
It isn't necessarily all or nothing.
Thank you for the reply! I added a new picture under answers i hope i understood your explanations correctly?
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Is this what u mean? So this should be the right answer?
Date Posted:
3 years ago
Yes.
Ahh i see! Okay thank so much for your help!!! I really appreciate it!!
Even for basic electrophilic addition of something like Cl to methylbenzene (toluene) you'll usually see the para addition to be the major product and ortho addition to be the minor product, despite very small steric hindrance.
https://www.masterorganicchemistry.com/2018/01/29/ortho-para-and-meta-directors-in-electrophilic-aromatic-substitution/
https://www.masterorganicchemistry.com/2018/01/29/ortho-para-and-meta-directors-in-electrophilic-aromatic-substitution/
Ok sure will check out the link! Thank you very much!
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