Cycloserine is an antibiotic isolated from the microbe Streptomyces orchidaceous. It is used in conjunction with other drugs for the treatment of tuberculosis.

a) What is the molecular formula of this compound?

b) How many sp³-hybridized carbon atoms are present in this structure?

c) How many sp²-hybridized carbon atoms are present in this structure?

d) How many sp-hybridized carbon atoms are present in this structure?

e) How many lone pairs are present in this structure?

f) Identify each lone pair as localized or delocalized.

g) Identify the geometry of each atom (except for hydrogen atoms).

h) Draw all significant resonance structures of cycloserine.

Transcribed Image Text:

NH2 N. Cycloserine