The rate constant for the cyclisation of fig C2 is a few times smaller than the
ID: 852656 • Letter: T
Question
The rate constant for the cyclisation of fig C2 is a few times smaller than the (second order) rate constant for reaction of PhCHCl with PHCH2NH2, and thus thousands of times slower than expected for the formation of a 5-membered ring. Why is that? With C3, it is base catalysed reaction of C3 gives an ether and a sulphide (a thioether) as products. What are their structures?
The rate constant for the cyclisation of fig C2 is a few times smaller than the (second order) rate constant for reaction of PhCHCl with PHCH2NH2, and thus thousands of times slower than expected for the formation of a 5-membered ring. Why is that? With C3, it is base catalysed reaction of C3 gives an ether and a sulphide (a thioether) as products. What are their structures?Explanation / Answer
The rate is greatly different due to entropy consideration. When in C2, the position of NH2 is such that this is very available but in a bimolecular reaction, a molecule has to approach in a proper diretion, and energy for the reaction to occur.
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