Oseltamivir (sold under the trade name Tamiflu®) is a prescription antiviral drug th...

Oseltamivir (sold under the trade name Tamiflu^®) is a prescription antiviral drug that is used in the treatment of both Influenza virus Type A and Influenzavirus Type B.

(a) Identify the various functional groups present in Oseltamivir. Is the amine group primary, secondary, or tertiary? (Chapter 1)

(b) What is the molecular formula of Oseltamivir? (Chapter 1)

(c) Place a check mark in the box next to all the words that describe Oseltamivir:

Chiral

Achiral

Optically active

Optically inactive

Racemic

(d) Label all stereocenters (if any) present in Oseltamivir as either R or S.

(e) Draw an enantiomer of Oseltamivir.

(f) Draw a diastereomer of Oseltamivir.

(g) Oseltamivir is synthesized starting from shikimic acid, which can be partially hydrogenated to form the compound shown below on the right. Draw alternative chair conformations of this molecule and label the more stable and less stable conformations. (Chapter 2)

(h) What is the maximum number of stereoisomers possible for Oseltamivir?