c



 





Ha: Ha is the most downfield because it is attached to a
benzene ring and is ortho to a great electron donating
group. However, the electron donating groups are most
effective at shielding toward para hydrogens, and so Hb is
more upfield than Ha.

Hb: 6.58 ppm. Hb is the second most downfeld because it

is attached to a benzene ring and is para to a great electron
donating group. The electron donating groups are most
effective at shielding toward para hydrogens, and so Hb is
slightly more upfield than Ha.

Hc: The major rotomer, which has the ester group pointing
up, is further away from the two hydrogens than it is from
the two hydrogens of the minor rotomer. Because these two
hydrogens are close to the nitrogen, the ester group, and the
ketone group to the left (in 3D structure), it is also fairly
deshielded. It couples with many of the hydrogens around
it, thus the peak is broad.

Hc: The minor rotomer, which has the ester group pointing
down, is closer to these two hydrogens, and thus the level
of deshielding increases. Because these two hydrogens are
close to the nitrogen, the ester group, and the ketone group
to the left (in 3D structure), it is also fairly deshielded. It
couples with many of the hydrogens around it, thus the
peak is broad.
Hd: It¶s a singlet because it is orthogonal to the other
hydrogen atoms around it. It is also close to the nitrogen
and ester groups in the 3D formation, so it is fairly
deshielded.

He: Major rotomer, which has the ester group pointing up,
is much closer to this H, thus making He more deshielded
than it does to the H in the minor rotomer. It couples with
one Hj that is not in a 90 degree angle to it in a doublet.

He: Minor rotomer, which has the ester group pointing

down, is much farther away from this H, thus making He
more shielded than it does to the H in the major rotomer. It
couples with one Hj that is not in a 90 degree angle to it in
a doublet.

Hf: 3H single that is next to the ester group. Hf is more

deshielded than Hg because it is next to an ester, and not
merely an ether.

Hg: 3H singlet that is next to the ether group. It is more

shielded than Hf because it is next to only one oxygen,
whereas Hf is close to two oxygens of the ester.

Hh: These hydrogens are near a ketone group and other

hydrogens, thus accounting for the 2.70-3.20 ppm
multiplet.
Hi: Next to an oxygen, thus the 2.64 ppm. It¶s also a
doublet since it is at a 90 degree angle to one of the
hydrogens.

Hj: Some of the most shielded hydrogens because they are

far away from most electronegative atoms. The broad range
of chemical shifts indicates many different hydrogens in
multiplets.

Hk: Even more shielded hydrogens. These hydrogens are

the most shielded hydrogen atoms because they are farthest
away from the electronegative atoms. The broad range of
chemical shifts indicates many different hydrogens in
multiplets.