Question

please answer all 6 points breakout. (a-f)

13. (16 pts) Compound P was a pleasant smelling, colorless liquid with a boiling point of 218 degrees C. It had no effect on either red or blue litmus paper. A mass spectrum of Compound showed a molecular ion at 134 with a base peak at 105. When an ir spectrum was taken as a liquid film of Compound P, an intense peak was observed at 1683 cm. Both proton nmr and carbon-13 nmr were taken of Compound P, and both are shown on the next page. For the proton nmr spectrum, the number of protons contributing to a resonance is shown above the resonance multiplet. For the carbon-13 nmr spectrum, the multiplicities are NOT given. Note that two carbon-13 peaks are very close to each other. Tables with reference infrared frequencies and nmr chemical shifts are given on the two pages just before the answer sheet. Points Breakout Interpretation of infrared, 2 pts Calculation of molecular formula, 2 pts Calculation of degrees of unsaturation, 2 pts Interpretation of proton nmr (show deductions), 3 pts Interpretation of carbon-13 nmr (show deductions), 3 pts Correct structure of Compound P (including reasoning), 4 pts

Answer 1

(a) intense freak at 1683 cm conjugated carbonyl carbon may be i (b) m/2=134 Using Rule of 13 = 133 134 . Go Hiu .: O- is there ( 10 Cty) [Ca 4,00 € Molecular formula (c) IID = deti - 24 2 (9+) -1% - 10-5 =2 Fing) IHD-2 Degreef unstweration d) NMR dedectes (ppm) Integration splutting Possible fragment 1.18 3H triplet CH₂ - CH2 3. 54 2H quartet CH₂ - CH3 7.9 12H doublet Aromatic - CH 7.5-706 3H Multiplet Aromatur -CH are e) CNMR &(ppm) Indensation splitting possible tegiment 8.4 | CH3 o 31 -CH2-d- 136.7 - 3 Aromatic - C Aromatic -C 12 2 2 If This based on all information we concluded structure is Aromatie Ketone that is sweet Smelling

it is 7.9 1018 3.5 7.3- 7.6 . Propiophenore) 126 136 127 Val 1/ 200 737 8.4 132 120 127 Thus the whole information was utelised and product structure was deduced.