QuestionStereochemistry / nitrogen inversion, Curtin-Hammett
The structures of conformer A and B as well as the products C and D in the following free energy profile diagram for the SN2 reaction of tropane with isotopically labelled ¹³CH₃I is :
- (a) A = N-CH₃ over the propano (six-ring) side, lone pair over the ethano bridge; B = N-CH₃ over the ethano bridge; C = ¹³CH₃ on ethano side, CH₃ on six-ring side; D = CH₃ on ethano side, ¹³CH₃ on six-ring side
- (b) A = N-CH₃ over the six-ring side; B = N-CH₃ over the ethano bridge; C = CH₃ on ethano side, ¹³CH₃ on six-ring side; D = ¹³CH₃ on ethano side, CH₃ on six-ring side
- (c) A = N-CH₃ over the ethano bridge, lone pair over the six-ring side; B = N-CH₃ over the six-ring side; C = ¹³CH₃ on ethano side, CH₃ on six-ring side; D = CH₃ on ethano side, ¹³CH₃ on six-ring side
- (d) A = N-CH₃ over the ethano bridge, lone pair over the six-ring side; B = N-CH₃ over the six-ring side; C = CH₃ on ethano side, ¹³CH₃ on six-ring side; D = ¹³CH₃ on ethano side, CH₃ on six-ring side
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