Part 1. • Draw the structures of the three C5H12 structural isomers below. • • Make models of the molecules to be sure that you understand which of the carbons are identical by symmetry. Fill in the table, using NMR spectra 1a-c. Structure IUPAC Name Number of C's # of Types of C's (Skeletal) Labe 1° 2° 3° 4° 1° Corr.* NMR(s) 2° 3° 4° Tot *"Corr." Is an abbreviation for "Corresponding" 1a 1b 15 30 25 20 15 10 PPM 0 35 30 35 1c 25 -25 20 20 15 10 PPM 0 35 30 25 20 PPM 15 10 C (cour waste)

Identify and draw the structure of the important peaks in the MS spectral data of C9H8O given below.

6) The compound with the molecular formula C4H10O was synthesized. It was further analyzed using IR spectroscopy. The spectrum of the compound is illustrated below. Identify the structure of a compound. Justify your answer. Identify as many peaks on its IR spectrum as possible. (5 points) 100 80 60 60 %T 40 20 20 0 4000 R2020-93124TM 3000 2000 1500 1000 400 Wavenumber [cm-1]

The number of peaks in the ¹H-NMR spectrum of a com-pound depends on the number of different kinds (environments)of H atoms. How many peaks appear in the spectrum of each iso-mer of C₄H₁₀and of C₅H₁₂

1. Draw two constitutional isomers of the formula C6H11B1. Explain how you would differentiate those molecules using either spectroscopy or spectrometry. You only need to differentiate them using one example.

%3D %3D %3D %3D %3D %3D IR spectrum shown below. Draw a structure that best fits this data. A molecule with the molecular formula of C3H8O produces the 000 000 0007 000 0000 Wavenumbers (cm') Drawing

CHM 2410Z - Organic Chemistry I Lab 2) Consider the following molecules and choose the two represented by the spectra below. Use the IR spectra to narrow the possibilities, and then use the NMR data to confirm your choice. a. 1H NMR data: OH 8 3.6 ppm (2H, quartet) 8 3.0 ppm (1H, triplet) 82.6 ppm (2H, triplet) 8 2.2 ppm (3H, singlet) 8 1.8 ppm (2H, pentet) b. 1H NMR data: 83.7 ppm (3H, singlet) 82.6 ppm (1H, septet (7)) 81.2 ppm (6H, doublet) OH IR spectrum: 100 4000 IR spectrum: OH Дог ная 3000 lion OH 0.8 0.4 2000 VNUMBER U 0.6 3000 1500 2000 Wavenumber (cm-1) OCH 3 1000 1000

5. Determine the structure of a compound with a molecular formula of C4H8O2 with the 13C and 'H NMR spectra below. No peaks exchange with D20 on the 'H NMR spectrum. ada I=2 |=3 1=3 1.2 4.0 4.0 3.0 2.0 1.0

A'2 The 'H-NMR spectra of cyclohexanol and cyclohexanone are given below. Identify which spectrum belongs to which compound and assign the peaks in each spectrum that substantiate your decision.

Propose a structure consistent with each set of data.a. a compound that contains a benzene ring and has a molecular ion at m/z = 107b. a hydrocarbon that contains only sp3 hybridized carbons and a molecular ion at m/z = 84c. a compound that contains a carbonyl group and gives a molecular ion at m/z = 114d. a compound that contains C, H, N, and O and has an exact mass for the molecular ion at 101.0841