Unknown Number: Molecular Formula: Index of Hydrogen Deficiency: Structure: Mass

Question

Unknown Number:
Molecular Formula:
Index of Hydrogen Deficiency:
Structure:
Mass Spec
Molecular Weight:
Important Fragments; what are they and what do they mean? (base peak structure, is there a halogen, is there a benzene ring, is there an odd number of nitrogens, other important fragments that tell something about the structure)
IR
Is there an OH? Wavenumber?
Is there a carbonyl group? If so what type (acid. ester, amide, aldehyde, ketone etc.)? Wave number?
Other important peaks (terminal alkyne, cyano group, aromatic, alkene, nitro group, amine etc.) and where are they?
1H-NMR
Identify every signal; chemical shift, what is it due to( i.e what type of proton, aromatic, aldehydic, O-H, N-H, vinyl etc.) and how many protons does it represent.
13C-NMR
How many different types of carb
ons are present?
What type of carbon does each signal represent?
How can you put the skeleton together?
LOGIC:
Carefully, and thoroughly show how you used the spectral data to determine your structure. Show how all your data confirms your structure. Especially useful is using 1H-NMR as confirmation.

Explanation / Answer

Unknown Number:
Molecular Formula: C5H8O
Index of Hydrogen Deficiency:

Structure: CH3CCCH2CH2OH

Mass Spectrometry

Molecular Weight: 84

Important Fragments; what are they and what do they mean? (base peak structure [M – OH]+ = 66, is there a halogen (no halogen), is there a benzene ring (No), is there an odd number of nitrogens (No), other important fragments that tell something about the structure)
m/z 83 peak is correspond to [M - H]+

IR
Is there an OH? Wavenumber?

Yes, around 3300 cm-1

Is there a carbonyl group? If so what type (acid. ester, amide, aldehyde, ketone etc.)? Wave number?

No

Other important peaks (terminal alkyne, cyano group, aromatic, alkene, nitro group, amine etc.) and where are they?

Alkyne (2250 cm-1)

1H-NMR
Identify every signal; chemical shift, what is it due to (i.e what type of proton, aromatic, aldehydic, O-H, N-H, vinyl etc.) and how many protons does it represent.

All are aliphatic proton. 1H (OH), 4H (CH2), 3H (CH3)
13C-NMR
How many different types of carb

Five signals correspond to carbon.
Most of the things detailed in spectrum itself.

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