give the structure that corresponds to the following molecular formula and 1H NM

Question

give the structure that corresponds to the following molecular formula and 1H NMR spectrum: C4H10O2: delta 1.36 (3H, d, J=5.5Hz); delta 3.32(6H,s); delta 4.63 (1H,q, J=5.5 Hz)

Explanation / Answer

Molecular Formula : C7H16O ____ [ CnH2n+2O ] ----> Acyclic Saturated Compound ----> Alcohol _ or _ Ether H-NMR Spectrum : Singlet at ~ 1.38 ppm ; Area 1275 ; Disappear after Shaking with D2O ----> 1 Proton ; " acidic " proton - exchangable with D from D2O ; No Peak Splitting ( No Proton at Adjacent Carbon ) ----> Proton at -OH Group of Tertiary Alcohol Quartet at ~ 1.42 ppm ; Area 7473 ----> 6 Identical Protons ; Located closer to Alcohol Group ; Peak Splitting by 3 Protons at Adjacent Carbon ----> [ Carbon with no H -- CH2 -- Methyl Group ] ----> 3 Identical -CH2- Groups Triplet at ~ 0.9 ppm ; Area 11238 ----> 9 Identical Protons ; Located far away from Alcohol Group Peak Splitting by 2 Protons at Adjacent Carbon ----> [ -- Carbon with 2 H -- CH3 ] ----> 3 Identical -CH3 Groups Conclusions : Tertiary Alcohol [ One -OH Group ] Three ( 3 ) Identical -CH2-CH3 Groups attached to Tertiary Carbon [ Three -CH2- ( 6 Protons ) ; Three -CH3 ( 9 Protons ) ] Structure ____ ( CH3CH2 )3C-OH IUPAC Name ____ 3-Ethyl-3-pentanol

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