Identify each of the following compound (C4H8O2) from its molecular formula and its IR and 1H NMR spectra: Note: Offset means: “add “offset to 8 ppm.”Assign the peaks in NMR spectrum. You must indicate clearly the hydrogen/s of the molecule responsible for the peak/s.

A compound and its ¹H-NMR spectrum are shown below. Assign peak 1 and peak 2 in the spectrum to the hydrogen(s) labeled in red. i. a H3C- 10 C4H8O₂ Compound C b c -O—CH,CH3 2006 Brooks/Cole Thomson Submit Answer C 9 ↑ Which labeled hydrogen(s) correspond to each peak? peak 1: peak 2: 8 7 6 2H 5 Chemical Shift (8) Peak 3 Retry Entire Group 6 more group attempts remaining 3. 3H Peak 2 3H Peak 1 0 ppm

Steps in Spectral Identification: •Identify major peaks in IR spectrum, if any. •Deduce structural fragments for each of the 1H NMR spectral signals. •Give the structure of the compound •Assign the signals in the 1H NMR spectra to specific protons •Assign carbons to the peaks in the 13C NMR spectrum Step 1. Calculate the degree of unsaturation for the unknown. Step 2. Determine the functional group from IR Step 3. Analyzing the MS spectrum Step 4. Analyzing the 1H NMR spectra Determine the number of different kinds of protons Step 5. Analyzing the 13C NMR spectra

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The proton NMR and IR spectra of an unknown compounds is shown on the next page. Using the molecular formula C5H12O, find L a) the index of saturation b) the structure of the unknown compound c) assign the absorption bands to the functional groups in the IR spectrum d) label all peaks in the NMR spectrum, and label the same peak on the hydrogens in the structure Transmittance (%) 100 80 60 40 20 0 3500 CT TYCE Tabdf62 2874.30 2500 Wavenumber (cm-¹) 3000 2000 1466.09 1500 1307.78 1124.04 21 seser 908.46 1000 37.21

1. How would you differentiate between the following sets of molecules by IR and ¹H NMR? Consider: IR frequency and shape/intensity and NMR chemical shift, integration, and splitting. (There are multiple ways for each, but I am looking the 'blinding headlights' clue that would jump out at you.) VS CI OH VS VS ai i VS OH VS OH

Determine the compound (name or structure) from the data. Explain features from each data.  Molecular formula: C6H5Br Use molecular formula to determine IHD IR: Identify the presence/absence of five key functional groups NMR: Analyze this last. Consider multiplicity and peak area to confirm compound. The 5 H peak area covers both peaks (at 7.1 and 7.5 ppm Structure?

Which of these choices best describes the interpretation of the following peak that may be recorded in a 'H NMR spectrum? 2.5 8 (2H, d). The underlined hydrogen atom is intended to be the one producing the peak that we are interpreting. O=C-CH,CO2H O=C-CH2CHX2 O=C-CH2CH2X O=C-CH2CH3 None of these interpretations describes this peak.

Steps in Spectral Identification: •Identify major peaks in IR spectrum, if any. •Deduce structural fragments for each of the 1H NMR spectral signals. •Give the structure of the compound •Assign the signals in the 1H NMR spectra to specific protons •Assign carbons to the peaks in the 13C NMR spectrum Step 1. Calculate the degree of unsaturation for the unknown. Step 2. Determine the functional group from IR Step 3. Analyzing the MS spectrum Step 4. Analyzing the 1H NMR spectra Determine the number of different kinds of protons Step 5. Analyzing the 13C NMR spectra