Question

TнсттисE A . 00 5D 1000 4100 3000 00 NVENU ERIs 1383 39 1346 5D J017 16 3333 2963 2930 2878 4 969 8 1293 6B 1236 6D 1100 32 1059 B 305 62 888 69 858 755 82 74 5 72 1656 84 L051 1466 84 26 I066 479

Answer 1

IR spectrum:
peak at 3300 cm^-1 corresponds to the stretching frequency of OH group.

Mass spectrum:
Molecular ion peak = 60
Divide molecular ion peak by 13 to get no. of CH units in the molecular formula.
60/13 = C₄H₁₂
from IR we see that there is an oxygen atom. so subtract equivalent amount of CH unit to add oxygen atom.
  C₄H₁₂
+ O
- CH4
----------------------------
= C₃H₈O is the desired molecular formula.

NMR spectrum:
* peak for OH proton is a singlet at 2.2 ppm.
* peak for CH₃ proton is a triplet at 1.1 ppm.
* peak for -CH₂-C proton is a sextet at 1.5 ppm.
* peak for -CH₂-O proton is a triplet at 3.8 ppm because it is attached to highly electronegative atom. So, its highly deshielded.

structure of Compound is CH₃-CH₂-CH₂-OH