In 1914, the chemist Emil Fischer carried out the following conversion in which optically active starting material was transformed into a product with an identical melting point and an optical rotation of equal magnitude and opposite sign. No bonds to the asymmetric carbon were broken in the process.

Show that this result is consistent with either tetrahedral or pyramidal geometry at the asymmetric carbon.

Transcribed Image Text:

CH₂CH₂CH3 T H—C—CONH, I CO₂H several reactions CH₂CH₂CH3 | H-C—COH | CONH₂