Question

Draw the Skeletal Structure of the Unknown Compound, with NMR given below

Information: Each spectra belaw was obtained from a pure compound. Mass Spectrum parent peaks (M) are listed for all examples. IR peaks listed are strong is) unless otherwise indicated for signals above 1500 cm 'H NMR Spectra, the integral is given in number of hydrogens (WH) or as a relative ratio. Important coupling constants (-values) are listed next to the peaks for some examples. For some spectra, an inset (grey box) is also given showing a "zoom-in" on an important part of the spectrum. Mass Spectrometry (not shown): [M] = 116 m/z Infrared Spectroscopy (not shown): 3100, 2963, 2973, 1709 cm 'H Nuclear Magnetic Resonance. PPM 2H9H c Nuclear Magnetic Resonance. 180 160 140 ' 120 . 100 80

Answer 1

spectral Data based on Mass; IR, HINHA ( NHR he probable structure is . 93 COW Hic - ¢ -CH₂- & - CH2 3,3-Di reky, butanuic acid H' NMR: * It consists of 3 types of protons, 3 signals appears in the HI NMR spectrum, which are labelled abc. CH3 (c) o .Hgc-Ć-Clyć - ob - CH₂ ) Type of Integration | Noriber of I Multipicity Proton neighbour papo tome (nt) a ) I S value (PPM) TH singler 18 Рент singlet | 21 PPM : singler 0.9 per

c in ch NMR. NMR : u types of carbons, 4 signals dçh3 Hoc & CH₂ - Cow Ide 15 a H₂C-CCT 6" (a) (a)-Type Carbon & vaner 175 PPM (b)- Type carbon s vane: 48 PPI (C) and (d) Type carbon svake: 88 pan. From IR Data: 3100 cricoh Stretching 2a63 Cal" 1709 cn ch stretching. .co Stretching.

Mass spectrul Duta: - CH3 70 en ♡ HEC kccupé nou Hz( C-Clg - C-OH CH3 Hole colar Ion Peak A = 116