Question

1. Provide a structure that is consistent with the following data C,H,O C,H, Br 10000 1000 11001 CD UL C.H.0 000 000 LA

Answer 1

Hi i have used following table (more specific to these 3 problems) during structure elucidation, as given spectra does not have any peak picking. Hence clear cut closer range only possible. I tried my best, if you have anything queries please comment below at comment section.

a) compound is 3-methyl-1-butanol

b) compound is 3-bromopropyne

c) compound is Propiophenone

Alcohol
O-H	(stretch, H-bonded)	3200-3600	strong, broad
O-H	(stretch, free)	3500-3700	strong, sharp
C-O	(stretch)	1050-1150	strong
Alkane
C-H	stretch	2850-3000	strong
-C-H	bending	1350-1480	variable
Alkyl Halide
C-F	stretch	1000-1400	strong
C-Cl	stretch	600-800	strong
C-Br	stretch	500-600	strong
C-I	stretch	500	strong
Alkyne
C-H	stretch	3300	strong,sharp
$//img.homeworklib.com/questions/ff7ed710-75d0-11ea-9777-2744bbccff8b.gif?x-oss-process=image/resize,w_560$	stretch	2100-2260	variable, not present in symmetrical alkynes
Aromatic
C-H	stretch	3000-3100	medium
C=C	stretch	1400-1600	medium-weak, multiple bands

Ketone
acyclic	stretch	1705-1725	strong
cyclic	stretch	3-membered - 1850            4-membered - 1780 5-membered - 1745 6-membered - 1715 7-membered - 1705	strong
a,b-unsaturated	stretch	1665-1685	strong
aryl ketone	stretch	1680-1700	strong

H,C OH Br : 3-methyl-1-butanol 3-bromopropyne propiophenone

Hope this helped you!

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