¹H-NMR Spectra 2 M.F. = C₁1H₁2O 15 15 -∞ 15 15 6 15 -LO 5 PPM 4 2) 3 -~ 2 31

¹H-NMR Spectra 3 M.F. = C₂H₁3NO 1 S 10 -00 8 6 PPM 4 N 21 3 ſ 2[2] -~ 2 3 j

¹3C NMR Spectrum (CDCI, 25MHz, ¹ H decoupled, solvent signals removed for clarity) Not sure how to interpret this C NMR. The molecular formula is C9H100 200 13C NMR Spectrum (CDCI3, 25 MHz, ¹H decoupled, solvent signals removed for clarity) d S 180 160 140 120 Ć 100 ppm 80 60 40 20 0

A student performed a series of reactions and obtained the spectral data provided. The reaction sequence is shown below.. What are the structures for A, B, C, and D? Compound B NMR (relative integrated areas below peaks) CH;CH,O°N 1. BHTHF N-bromosuccnimide A CH;CH,OH B 2. H,O,/OH- D hv reflux Compound A NMR (relative integrated areas below peaks) PPM 5 Compound B IR INFRARED SPECTRUM PPM 5 1 6 0.8 Compound A IR INFRARED SPECTRUM 0.6 0.8 0.4 0.4 0.2- 3000 2000 Wavenumber (cm-1) 1000 The MS of compound B shows an M+ peak at 198 and an M+2 peak at 200 with a relative abundance of 1:0.97 2000 Wavenumber (cm-1) 3000 1000 Transmitance Relative Transmittance

PART 2: NMR SPECTRA #1: C4H,Cl- no important IR peaks are seen. 3.5 2H 3.0 possible structure 2.5 300 MHz 'H NMR In CDC3 2.0 it wa 1.5 2H 2H 1.0 3H 0.5 0.0

Saturated aldehyde Aromatic aldehyde At what position would you expect to observe IR absorption for the carbonyl groups in the following molecules? Infrared Absorptions of Some Aldehydes and Ketones. Carbonyl type Absorption cm-1 1730 1705 Example CH3CHO PhCHO a,ẞ-Unsaturated H2C=CHCHO 1705 aldehyde Saturated ketone CH3 COCH3 1715 Cyclohexanone 1715 Cyclopentanone 1750 Cyclobutanone Aromatic ketone 1785 PhCOCH3 a,ẞ-Unsaturated ketone H2C=CHCOCH3 1685 1690 Molecule #1: Molecule #2: CHO CHO CH3 cm-1 cm -1

Please identify Molecule A, formed from the reaction shown, from the 13C NMR spectra shown. All peaks below are single peaks (no overlapping peaks). Inset is an expansion of the downfield section of the spectra.

23Na has no NMR frequency. What is its magnetogyric ratio? A) 101.1 x 10\^7 T-1 s-1 B) 26.75 x 10\^7 T-1 s-1 C) 7.081 x 10\^7 T-1 s-1 D) 0.9377 x 10\^7 T-1 s-1

is the product supposed to be 2- methyl-3-pentanol?

¹H-NMR Spectra 3 M.F. = C₂H₁3NO 1 S 10 -00 8 6 PPM 4 N 21 3 ſ 2[2] -~ 2 3 j