Question

Doxycycline is an antibiotic used to treat a wide variety of bacterial infections. The structure of doxycycline is given below. Answer the questions about this structure.

(b) Determine the configuration (c) What is the geom (a) Which orbitals are used for bonding by (Check all that apply) descriptor for the ring fusion at E? of carbon atoms C and D Carbon A Carbon B cis trans sp sp sp sp O sp sp H3C CH (d) Which type of carbon is at the positions A and D? CH OH OH primary primary NH secondary secondary O tertiary O tertiary OH OH OH O quaternary O quaternary continued below (e) Identify the functional groups F, G, H, and l. Select answer Select answer Select answer Select answer

Answer 1

a) Carbon - A - sp \(^{3}\) Carbon \(-B-s p^{2}\) and \(p\)

b) Configuration of \(\mathrm{C}\) and \(\mathrm{D}\) :

\(\mathrm{C}=\mathrm{S}\) and \(\mathrm{D}=\mathrm{R}\)

c) Geometric descriptor for the ring fusion at \(\mathrm{E}=\) cis

d) Type of carbon at the position \(\mathrm{A}\) and \(\mathrm{D}\) :

\(\mathrm{A}=\) primary

\(\mathrm{D}=\) tertiary

e) Functional groups:

\(\mathrm{F}=\) tertiary amine \(\mathrm{G}=\) amide

\(\mathrm{H}=\) ketone \(\mathrm{I}=\mathrm{alcohol}\)

Answer 2

(a) In Doxycycline, sp³ orbitals are used to formation of carbon A and sp² orbitals are used to formation of carbon B.

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(b) In Doxycycline, the carbon C has (S)-configuration and carbon D has (R)-configuration.

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(c) In Doxycycline, the geometry descriptor for the ring fusion at E is cis-configuration because the H and OH groups are in same side of the plane.

CH3 H,C CH3 OH E H H- он (cis-configuration) NH2 он OH Doxycycline

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(d) In Doxycycline, the carbon A is primary carbon because this carbon is bonded with only one carbon. The carbon D is tertiary carbon because this carbon is bonded with three carbons.

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(e) In Doxycycline, the functional group for F is tertiary amine, the functional group for G is amide, the functional group for H is ketone, and the functional group for I is alcohol.