Question

2) Megace (megestrol acetate, USP) is a synthetic derivative of the naturally occurring steroid hormone progesterone. MEGACE Oral Suspension is indicated for the treatment of anorexia, cachexia, or an unexplained significant weight loss in patients with a diagnosis of acquired immunodeficiency syndrome (AIDS). a) (5 pts) Outline and name five functional groups present in this compound b) (1 pt each + 1 pt) Place asterisk (*) next to each chiral carbon. How many stereoisomers of this compound are possible? c) (1 pt) How many carbons are present in this compound? → d) (1 pt) How many highly electronegative atoms (oxygen or nitrogen atoms) are present in this compound? e) (1 pts) How many charged groups would you expect to arise on this compound when in blood plasma at physiological pH of 7.40? (1 pts) Would you expect this compound to be highly soluble, soluble, slightly soluble, or insoluble in blood plasma? Support your answer with a clear argument. CH151 - Homework 6 - Organic Chemistry - Y3

Answer 1

The answers are explained in the uploaded image.

a) There are five different functional groups in the molecule

1. Ester functional group

2. Ketone functional group

3. Alkene functional group

4. Methyl functional group

5. Methyl ketone functional group

b) There are 6 chiral carbons in the molecule. 64 different stereoisomers are possible to the given molecule.

c) There are 24 carbon atoms in the molecule

d) There are 4 highly electronegative atoms are present in the molecule.

To metigt ketone Ester functional group. El Alkene Ketone functional group methyl group functional group. C Estes-R-20-2 Ketone - RE-R These five functional Alkene -c=c- group are present in the compound methyl citly & are mentioned at their respective menys kelone -CH₂-C positions. 6 chiral carbons are present which have given at (t) symbol. These are the chiral carbons as at each of these - carbons four different groups are attached Number of stereo isomers can be calcatated from the formula 22 where in a number of chiral carbons. Hence stereoisomers = 2 = 26 = 64 estexeo isomers. There are 24 carbons in this compound . Numbering is given in a random fashion to all available carbon atoms. d, four BOS Four oxygen atoms are present in this compound. No nitrogen atoms are present