Question

Propose a reasonable structure based on the molecular formula, the 1H NMR, and the proton–decoupled 13C NMR data below. The unknown compound has a molecular formula of C7H16O and * = CH2 by DEPT.

Propose a reasonable structure based on the molecular formula, the 'H NMR, and the proton-decoupled 13C NMR data below. The unknown compound has a molecular formula of C7H160 and * = CH2 by DEPT. 'H NMR 3H 8H 13C NMR 2H (CH3)4 Si 26 VIH them wwwwwwwwwwwwwwwwwwwww 3.5 0.0 60 20 3.0 2.5 2.0 1.5 1.0 0.5 300-MHz 'H NMR spectrum ppm (8) 40 13C NMR spectrum ppm (8) -OH

Answer 1

Degree of Unsaturation (DOU) can be calculated as follows

DoU   =   2C+2+N−X−H

               2

C is the number of carbons

N is the number of nitrogens

X is the number of halogens (F, Cl, Br, I)

H is the number of hydrogens

Molecular formula = C7H16O

Sites of unsaturation = 0

1H NMR data:

NMR peak value (ppm)	Protons	Indication
3.3	2H, triplet	CH2 attached to oxygen
1.3	2H, quintet	CH2 attached to two CH2
1.1	8H	Four CH2 having approx. same ppm value merging with each other
0.8	3H, triplet	CH3 attached to CH2
0.6	1H	Exchangeable OH proton

13C NMR data:

NMR peak value (ppm)	Indication
62	CH2 attached to oxygen
32	Aliphatic CH2
30	Aliphatic CH2
28	Aliphatic CH2
25	Aliphatic CH2
22	Aliphatic CH2
13	Aliphatic CH3

DEPT confirms molecule has six CH2 groups

Above data indicates the following structure

heptan-1-ol Exact Mass: 116.12