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Alkylation of lithium enolate P occurs through a
- a)chair-like transition state and the major product is N
- b)chair-like transition state and the major product is M
- c)twist boat-like transition state and the major product is M
- d)twist boat-like transition state and the major product is N
Correct answer is option 'C'. Can you explain this answer?
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Alkylation of lithium enolate P occurs through aa)chair-like transitio...
Alkylation of lithium enolate P occurs as follows:
- To get at the reason for this result we need to look at the conformation of the enolate intermediate.
- At this point, we shall generalize a bit more and write a structure that represents any enol derivative where X may be OH, O−, OSiMe3, NR2, and so on.
- We place the t-butyl group in an equatorial position because, as with cyclohexanes, it is so bulky it cannot go axial. This means that there is only one conformation to consider—the one shown below.
- Now, the electrophile must attack the π system of this conformation, and to do so it has to attack from more or less directly above or below because only then can it interact with one of the lobes of the p orbital at the enol position.
- The top of the molecule looks to be more open to attack so we shall try that approach first.
- As the electrophile forms a bond to the trigonal carbon atom, that atom must become tetrahedral and it does so by forming a vertical bond upwards. The result is shown in the diagram- the ring turns into a twist-boat conformation.
- After the reaction is over, the ring can flip into a chair conformation and the new substituent will then be equatorial.
- Thus, the reaction pathway will be as follows:
Hence, the Alkylation of lithium enolate P occurs through a twist boat-like transition state and the major product is M.
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Alkylation of lithium enolate P occurs through aa)chair-like transition state and the major product is Nb)chair-like transition state and the major product is Mc)twist boat-like transition state and the major product is Md)twist boat-like transition state and the major product is NCorrect answer is option 'C'. Can you explain this answer?
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