Answer:
The answer is 3-Phenylpropanoic acid (see attached structure)
Explanation:
From spectral data:
3005 cm-1 ⇒ carboxylic acid (broad band)
1670 cm-1 ⇒ C=C
1603 cm-1 ⇒ Aromatic C-C bond
H NMR frequency at 2.6 ppm, singlet, ⇒ OH with no surrounding protons, possible deshielding (clearer investigation of spectrum would be expedient).
Hence, our C9H10O2 compound has an aromatic ring and carboxylic acid group attached to it.
The conversion of 2 - butanol to 2 - nitrobutane involves conversion of 2 butanol to 2 - bromobutane and subsequently to 2 - nitrobutane.
In order to convert 2 - butanol to 2 - nitrobutane, an SN2 reaction is first carried out in which 2 - butanol is converted to 2 - bromobutane. This reaction proceeds with inversion of configuration at the chiral carbon as expected.
This product is subsequently reacted with silver nitrite in ethanol to yield 2 - nitrobutane along side silver bromide. Some alkyl nitrite is also produced as a by product. The components of the mixture are separated by fractional distillation. The scheme of the reaction is shown in the image attached to this answer. This reaction is only applied to primary and secondary alkyl halides.
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