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5-14) A compound A has a strong, broad IR absorption at 3200–3500 cm–1 and the proton NMR spectrum shown below. Treatment of compound A with H2SO4 gives compound B, which has the NMR spectrum shown at bottom and a molecular ion at m/z = 84 in its EI mass spectrum. Identify compounds A and B.

Question 5 of 5 A compound A has a strong, broad IR absorption at 3200-3500 cm 1 and the proton NMR spectrum shown below. Treatment of compound A with H gives compound B, which has the NMR spectrum shown at bottom and a molecular ion at m/z 84 in its El mass spectrum. Identify compounds A and B. chemical shift, Hz 900 300 600 2400 2100 1800 1500 1200 Draw compound A. 8966 i ii i compound A disappears after 1595 4461 D20 shake 616 H2SO4 chemical shift, ppm (o) Map

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Question 5 of 5 Map o A compound A has a strong, broad IR absorption at 3200-3500 cmand the proton NMR spectrum shown below.

он 2-methylpentan-2-0l Chemical Formula: CgH140 Exact Mass: 102.10 ChemNMR H Estimation 0.89 1.34 4.49 он 1.30 1.20 1.20 4 PP

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