One of the first drugs to be approved for use in treatment of acquired immune deficiency
syndrome (AIDS) was azidothymidine (AZT). Complete the Lewis structure for AZT.
a. How many carbon atoms are sp3 hybridized?
b. How many carbon atoms are sp2 hybridized?
c. Which atom is sp hybridized?
d. How many σ bonds are in the molecule?
e. How many π bonds are in the molecule?
f. What is the N=N=N bond angle in the azide (–N3) group?
g. What is the H–O–C bond angle in the side group attached to the five-membered ring?
h. What is the hybridization of the oxygen atom in the –CH2OH group?
a. Any carbon connected to four unique atoms is sp3 hybridized. Hence there are 6 carbon atoms that are sp3 hybridized in this molecule.
b. Any carbon connected to three unique atoms is sp2 hybridized. Hence there are 4 carbon atoms that are sp2 hybridized in this molecule.
c. An atom connected to only two unique atoms with 0 lone pairs is sp hybridized. Hence the center nitrogen atom in — N = N = N is sp hybridized.
d. Each single bond is made up of a sigma bond. Each double bond contains one sigma bond and one pi bond. Hence there are 33 sigma bonds present in this molecule.
e. Each double bond contains one sigma bond and one pi bond. There are 5 double bonds present in this molecule. Hence there are 5 pi bonds present in this molecule.
f. Since N atom undergoes sp hybridization, bond angle is 180°.
g. Tetrahedral geometry has 109.5 degree angles.
h. Any oxygen connected to two unique atoms with two lone pairs is sp3 hybridized
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