HNMR

A. This proton is found on an sp2 hybridized carbon and has no neighbors that contribute to vicinal coupling. This explains its singlet splitting pattern and its chemical shift around 5.98 ppm.

B. Protons labeled B are actually diastereotopic and are therefore found at different chemical shifts. They couple with each other and proton c and therefore show a splitting pattern of doublet of doublets. Diastereotopic coupling shows a high value of around 18 Hz while the coupling with proton C is around 5.5-7 Hz. These two hydrogen’s are found on sp3 hybridizned carbons and therefore show up around 3.03 and 2.55 ppm.

C. Proton C is found around 3.84 ppm-3.74 ppm due to an inductive effect from the neighboring oxygen atom. It is suspected that proton C is found on the H-NMR along with another proton, possibly proton O, due to their similar chemical characteristics of being right next to highly electronegative oxygen atoms. These show up as multiplets due to their complex splitting patterns due to several three bond neighbors.

D. Proton D is also suspected to be found on the H-NMR with another proton, possibly proton Q, due to their similar chemical characteristics of close-by neighbors with oxygen atoms. These protons can be found around 4.02-3.97 ppm and are hard to distinguish between protons C and O as well. They show up as multiplets due to complex splitting patterns with three bond proton neighbors.

E. The two protons labeled E are actually diastereotopic and therefore show up at different chemical shift values. They are found around 1.91 ppm and 2.8 ppm due to their attachment on an sp3 hybridized carbon and no nearby electronegative atoms. They show a large coupling value of around 18 Hz when coupled with each other but also show coupling with a nearby proton neighbor, proton D. These protons show up as ddd and br d which is slightly misleading, however, may be due to the magnification of the NMR machine.

F. Proton F is found on an sp2 hybridized carbon and therefore is found at about 5.41 ppm. The splitting pattern is a doublet of doublets due to its coupling with proton D at around 6.5 Hz and also its coupling with proton G, about 16 Hz. Proton G and proton F experience trans double bond coupling, thus explaining the large Hz value.

G. Proton G shows up around 5.67 ppm because it is also found on an sp2 hybridized carbon and shows the large coupling constant that matches proton F, about 16 Hz, thus confirming that the two couple with each other via trans double bond coupling. However, proton G shows as a doublet of doublets with one other proton for a value of 1.0 Hz. This may be due to a very small coupling effect with a distant proton, however, it may not be predicted which proton this is.

H. Protons labeled H are also a diastereotopic 3H pair. They are found on sp3 hybridized carbons and are fairly upfield at about 1.09 ppm and 0.95 ppm. They are singlets because of no nearby proton neighbors.

I. Protons I are found extremely upfield at about 0.01 ppm due to the effect of the nearby silicon atom which is less electronegative then carbon and therefore contributes to more shielding around the protons. They are singlet’s because of no proton neighbors.

J. J2 is found slightly more downfield then protons I due to being slightly more distant from the silicon atom, however, the protons still display a more shielded, upfield character at around 1.03 ppm. These 9Hs are singlets due to no nearby proton neighbors.

K. Proton K shows up around 1.4 ppm because of its association with an sp3 hybridized carbon.

L. Protons labeled L are actually diasteretopic 3H pairs. They are found on sp3 hybridized carbons and therefore are found around 1.18 ppm and 0.94 ppm. They have no nearby proton neighbors and therefore show up as singlet’s.

M. See explanation for C.

N. Protons N are actually diastereotopic, but may be displayed on the H-NMR around the same chemical shift of about 1.88 ppm-1.78 ppm due to their attachment on an sp3 hybridized carbon. These protons show as multiplets due to complex splitting patterns.

O. See explanation for C.

P. Protons P show up around 2.13 ppm due to a slight deshielding effect from a nearby oxygen atom although being attached to a sp3 hybridized carbon. These protons show up as multiplets due complex splitting patterns, possibly due to the fact that these protons are actually diastereotopic.

Q. See R for explanation.

R. Protons R are found as a diastereotopic pair around 2.67 ppm and experience a multiplet coupling pattern due to its complex splitting pattern with itself and several neighboring protons.

S. The 9H group of hydrogen’s around 0.89 ppm are found extremely upfield due to electron distribution from the very electropositive nearby silicon atom. These hydrogen’s are shown as singlets because they have no nearby neighbors.

T. The diastereotopic pair of T protons are found fairly downfield at about 4.56 ppm and 4.35 ppm due to a nearby oxygen atoms which deshields the two atoms. They show up as doublets due to coupling with each other, both with a coupling constant of about 11.5 Hz.

U. Protons U are found fairly downfield at around 6.76 ppm due to their association with carbon atoms in an aromatic ring. It also displayed a doublet coupling pattern of about 8.5 Hz with the other pair of protons in the aromatic ring.

V. Protons V are found 7.13 ppm due to their association with carbons on an aromatic ring similarly to protons U. They display doublet coupling peaks due to coupling with protons U and therefore have matching coupling constants of 8.5 Hz.

W. Protons W can be found near 3.73 ppm due to their close vicinity to an oxygen atom, thus causing deshielding. They are also found as singlets due to no nearby neighbors.

Y.   Z.  These protons can all be found around 7ppm due to their association with carbons on an aromatic ring. They show multiplets due to their complex splitting patterns around the ring.

A. This proton is found on an sp2 hybridized carbon and has no neighbors that contribute to vicinal coupling. This explains its singlet splitting pattern and its chemical shift around 5.98 ppm.

B. Protons labeled B are diastereotopic and can be found around 2.21 ppm. They display a multiplet splitting pattern due to complex splitting patterns with each other and proton C.

C. Proton C can be found around 3.57 ppm due to the deshielding effect provided by the nearby oxygen atom.

D. Proton D is displayed around 4.58 ppm due to a deshielding effect caused by a nearby oxygen atom. It also exhibits a multiplet coupling pattern due to complex coupling with diastereotopic protons E and proton F.

E. Protons labeled E are actually diastereotopic pairs that can be found around 2.25 ppm. They are displayed as multiplets due to complex splitting patterns with each other as well as proton d.

F. Proton F is found on an sp2 hybridized carbon and therefore is found slightly more downfield due to deshielding. Proton F is found around 5.52 ppm and expresses a doublet of doublet of 5.2 Hz (most likely with protons E) and 16 Hz which comes from the trans double bond coupling with proton G.

G. Proton G is also found on an sp2 hybridized carbon and is found around 5.71 Hz. It displayed a doublet of doublet splitting pattern with a small Hz value of 1.2 that may be from a distant proton neighbor and also 16 Hz which comes from its trans double bond neighbor, proton F.

H. Protons H are actually found in 3H diastereotopic pairs around 1.20 ppm and 1.14 ppm due to their association with sp3 hybridized carbons. They show singlet splitting patterns due to no effect of nearby proton neighbors.

I. Protons labeled I are a diastereotopic pair found near 4.18 ppm and 4.38 ppm due to the relative closeness to an electronegative oxygen, thus deshielding the protons. They show doublets due to their interactions with each other at about 11.2 Hz.

J. Proton labeled J is found directly attached to an oxygen atom and is therefore fairly downfield due to a large deshielding effect. It also displays a singlet splitting pattern due to no nearby proton neighbors.

K. Protons labeled K are diastereotopic pairs and show up at different ppm values of 2.18 ppm and 2.26 ppm. They couple with each other as well as with proton C and therefore display a doublet of doublets.

L. The protons L are found at 3.31 ppm due to a neighboring oxygen atom causing deshielding of the proton nucleus. Also, the splitting pattern of the proton is a singlet due to no nearby proton coupling.

M. Protons labeled M are diastereotopic pairs of 3H and are found around 0.90 ppm and 0.91 ppm due to their association with sp3 hybridized carbons. They also show singlet coupling patterns due to no nearby proton neighbors.

N. Protons N are actually diastereotopic and can be found around 3.13 ppm. They are slightly deshielded due to a neighboring oxygen atom and also show singlet coupling patterns due to no nearby protons to contribute to coupling.

O. These protons can be found around 6.99 ppm due to their association with an sp2 hybridized carbon involved in an aromatic ring. They show multiplet coupling due to complex coupling with other protons in the ring such as proton P.

P. These protons may be found around 6.92 ppm due to their association with an sp2 hybridized carbon involved in an aromatic ring. They show multiplet coupling due to complex coupling with other protons in the ring such as proton O.

Q. Protons Q are in a 3H group found around 4 ppm due to their closeness to a neighboring oxygen atom. They show singlet splitting patterns due to no neighboring protons to contribute to coupling.

R. This proton can be found around 3.71-3.64 ppm and may be categorized with proton T due to similar characteristics of being nearby an oxygen atom and also being associated in the same ring. Therefore, they show multiplet coupling due to complex coupling experienced between the two.

S. Protons labeled S are diastereotopic pairs found with diastereotopic protons U around 1.81-1.65 ppm due to their association with sp3 hybridized carbons. They display multiplet coupling due to complex coupling between each other as well as proton R and proton T.

T. See explanation for R.

U. See explanation for S

V. Proton V and W can be found around 2.97 and 1.54 ppm due to its relative closeness to an electronegative oxygen atom. It also shows multiplet coupling due to complex coupling patterns with neighboring protons.

W. See explanation for V

X. Protons X can be found around 2.90 ppm due to its closeness to a carbonyl group (usually bringing H-NMR peaks around 3 ppm). They are also singlet’s due to no nearby protons contributing to coupling.

Y. These 9H protons are found very upfield around 1.17 ppm due to their closeness to an electropositive atom, silicon, which shields the protons. They are also singlets because they don’t experience coupling with any nearby protons.

ZA.   ZB.  These hydrogen’s may all be found around 7-7.5 ppm due to their associations with aromatic sp2 hybridized carbons. They show multiplets because of complex coupling with protons amongst the ring.