5. Below is an IR spectrum of the Diels-Alder product. Identify and label peaks related to the carboxylic acid functionality. 400 2008 2000 VENUBE

6-Infrared spectroscopy provides valuable information about molecular weight. B) melting point. C) conjugation. 7-Which of the following is not an IR vibrational mode? stretching B scissoring C rocking D rolling A) A 8- Which of these molecules best corresponds to the IR spectrum below? O • H₂C. m m m m b) m m но OH c) 3300 2900 2800 1465 1450 1375 HO 9-A strong signal at 1700 cm-1 in an IR spectrum indicates the presence of a(n) A) C) carbonyl D) amine D) functional groups. alcohol B) ether 10-Deduce the structure of an unknown compound with molecular formula CsH12O using information given by its infrared spectrum. Intensity (peak): Frequency (cm¹¹): d E wagging B- •) nammm 1000 HO OCH, X 11-Which of the following bonds would be expected to have the highest frequency= double bond

III) Can 1H NMR spectroscopy be used to differentiate between the two compounds? Briefly explain why or why not. Predict the 1H NMR spectrum for each compound (include integration, multiplicity, and approximate chemical shift). For each set, be sure that you put them in a data table format!

In the attached H1-NMR, draw and identify each set of equivalent hydrogens in the structure and list peak they belong to in the NMR spectrum.

Can you use IR spectroscopy to differentiate between an Alkene and an arene?

3. The spin-decoupled 1C NMR spectrum of an unknown compound contains a peak near 8 210 ppm, and a 'H NMR signal near & 9.5 ppm. Which of the following compounds could be this unknown? А. (CH):ССНО В. СН:CH-CH,CH-ОН С. CНCH-0CH-Ph D. CHCH-CH-СООН E. PHCH2C(O)CH3

Identify the structure of the unknown compound from the given spectra. The letters on the NMR indicate the splitting pattern.@GMU 2020 Integrations: OA OB OD OE 7 5 -- DOM ►

300 MHz 1H NMR spectra in CDCl3 are shown below for five of the six isomers of dimethylphenol. Match each spectrum to the appropriate compound and assign the resonances of the spectrum to the appropriate protons in the compound.

2. Which C4H,Br isomers give rise to the two spectra shown below? b. 8 C. 8 7 7 6 5 5 34 4 8 (ppm) 33 32 PPM 4 8 (ppm) 2H t I 2H d 3 ند 3 2H 2H quint sext NH 2 1H m 2 6H d I C 3H 1.0 PPM 0 0

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