Proton Asssignment	Shift	Integration	Splitting Pattern
1	1.20	3H	Triplet
2	3.88	2H	Quartet
3	5.55	1H	Triplet
4	1.74	1H	Doublet of Doublets
5	1.99	1H	Doublet of Doublets
6	3.45	1H	Doublet of Doublets
7	1.70	1H	Doublet of Quintets
8	1.45	1H	Doublet of Quintets
9	1.62	1H	Doublet of Quintets
10	1.38	1H	Doublet of Quintets
11	1.34	1H	Doublet
12	0.88	1H	Doublet
13	0.89	3H	Singlet
14	1.81	1H	Doublet of Triplets
15	1.56	1H	Doublet of Triplets
16	2.40	1H	Doublet of Triplets
17	2.30	1H	Doublet of Triplets
18	2.38	1H	Doublet
19	2.12	1H	Doublet

Proton Shift Reasonings

1) The 1.20 ppm peak corresponds to the three hydrogens on the sp3 carbon. The peak shows up as a triplet due to the vicinal coupling with the two 3-bond neighboring protons.

2) The 3.88 ppm corresponds to the two hydrogens next to the oxygen atom. These protons are deshielded due to the inductive effect of the oxygen. This peak shows up as a quartet because of the vicinal coupling with the methyl group hydrgens.

3) The 5.55 ppm peak corresponds to the hydrogen atom within the cyclopentane. It is attached to two oxygens; the indicative effect from the oxygen atoms deshields the hydrogen resulting in its high ppm value. This peak shows up as a triplet due to vicinal coupling with the two hydrogen 3-bond neighbors.

4) The 1.74 ppm peak corresponds to the downward-facing hydrogen that is on the ethyl group inside of the cyclopentane. This peak is the farthest away from the oxygen that is coming off of the cyclopentane in an upward direction, and therefore it is more shielded due to the lack of inductive effect. This shows up as a doublet of doublets due to 2-bond coupling 3-bond coupling.

5) The 1.99 ppm peak corresponds to the upward-facing hydrogen that is on the ethyl group inside of the cyclopentane. This peak is more downfield due to inductive effect from the oxygen atom. This shows up as a doublet of doublets due to 2-bond coupling and 3-bond coupling.

6) The 3.45 ppm peak corresponds to the hydrogen in the cyclohexane that is close to the oxygen atom within the cyclopentane. Inductive effect of the oxygen contributes to the deshielding of this hydrogen. This peak shows up as a doublet of doublets due to the 3-bond coupling and W-letter coupling.

7) The 1.70 ppm peak corresponds to a proton within the cyclohexane that is facing downward. It is deshielded due to the inductive effect from the oxygen in the pentane. This peak shows up as a doublet of quintets due to the 2-bond coupling and 3-bond couplings.

8) The 1.45 ppm peak corresponds to the hydrogen within the cyclohexane that is facing upward. It is more shielded due to its further distance from the oxygen atom within the cyclopentane. This peak shows up as a doublet of quintets due to the 2-bond coupling and 3-bond couplings.

9) The 1.62 ppm peak corresponds to the downward facing hydrogen. It is deshielded due to its proximity to an oxygen atom. This peak shows up as a doublet of quintets due to the 2-bond coupling and 3-bond couplings.

10) The 1.38 ppm peak corresponds to the upward facing hydrogen. It is further away from oxygen and therefore more shielded. This peak shows up as a doublet of quintets due to the 2-bond coupling and 3-bond couplings.

11) The 1.34 ppm peak corresponds to the hydrogen attached to the same carbon as the methyl group coming off of the cyclohexane. This peak shows up as a doublet due to 3-bond coupling with the methyl hydrogens and the ethyl hydrogens.

12) The 0.88 ppm peak corresponds to the hydrogens on the methyl group attached to the cyclohexane. These hydrogens are attached to an sp3 carbon causing them to be upfield and shielded. This peak shows up as a doublet due to the 3-bond coupling with the hydrogen.

13) The 0.89 ppm peak corresponds to the hydrogens on the methyl group between the two cyclohexanes. These hydrogens are attached to an sp3 carbon causing them to be upfield and shielded. This peak shows up as a singlet because it has no neighbors and therefore no coupling.

14) The 1.81 ppm peak corresponds to the downward facing hydrogen. It is closer to the ketone, which contributes to its more downfield ppm. This peak shows up as a doublet of triplets due to 3-bond and 2-bond coupling.

15) The 1.56 ppm peak corresponds to the upward facing hydrogen. It is further away from groups attached to the cyclo-hexane and –pentane structures and therefore experiences no inductive effect and as a result is more shielded. This peak shows up as a doublet of triplets due to its 3-bond and 2-bond coupling.

16) The 2.40 ppm peak corresponds to the downward facing alpha hydrogen. It is deshielded due to inductive effect from attached ring and methyl structures. This peak shows up as a doublet of triplets due to 3-bond and 2-bond coupling.

17) The 2.30 ppm peak corresponds to the upward facing alpha hydrogen. It is more shielded due to its further proximity from the rest of the structure. This peak shows up as a doublet of triplets due to 3-bond and 2-bond coupling.

18) The 2.38 peak corresponds to the downward facing alpha hydrogen that is closer to the cyclopentane. It is deshielded due to inductive effect of the attached ring structure and ketone. The peak shows up as a doublet due to 2-bond coupling.

19) The 2.12 peak corresponds to the upward alpha hydrogen that is close to the pentane. It is more shielded because it is further away from the rest of the ring structure. This peak shows up as a doublet due to 2-bond coupling.